When I started this newsletter in June 2024, my goal was simple: to help the HubSpot ecosystem get tactical about what it takes to move past “basic CRM usage” and build true connected go-to-market excellence.

Since then, ConnectedGTM has grown into a community of builders, thinkers, and leaders. It’s been an incredible journey, from being one of the first dedicated newsletters in the space to partnering with some of the best HubSpot agencies and software providers in the world.

Today, I’m excited to share that ConnectedGTM has been acquired by Attribution Academy and will be merging into Ryan Gunn’s newsletter, Hubsessed.

I’ve loved building this newsletter in the HubSpot ecosystem and I’m forever thankful for your feedback, ideas, and encouragement over the last two years.

Why Hubsessed?

If you’ve been in the HubSpot ecosystem for any length of time, you know Ryan. Our paths first crossed years ago when we were at Arrows and Aptitude 8 respectively, and we’ve been collaborating ever since.

When Ryan was first getting Hubsessed off the ground, he reached out to get my advice on how to run a successful newsletter. Since then, I’ve watched him turn it into a critical resource technical HubSpot strategy and attribution expertise.

“Stuart built the blueprint for how to educate and empower the HubSpot ecosystem. As a mentor and a friend, he’s been instrumental in how I think about Hubsessed. I am incredibly honored to welcome the ConnectedGTM community and continue the work Stuart started.”

— Ryan Gunn, Founder of Attribution Academy

I’m excited for Ryan to take the tactical content you’re used to from ConnectedGTM and share new use cases and deep dives to help everyone trying to get more from their HubSpot account and grow their impact at their company.

What This Means for You

Ryan and I have worked to make sure this transition is as seamless as possible for everyone. Here is exactly what to expect:

• Free Subscribers: There is no action required on your part. You’ll stay on the free tier and will begin receiving emails from ryan@mail.hubsessed.io. You will also still have full access to the ConnectedGTM archive, which has been migrated over to the Hubsessed website.
  

• Paid Subscribers: Your subscription is being automatically transitioned to the Hubsessed Pro tier. You will maintain your current pricing and billing schedule. The only change you’ll notice is on your credit card statement, which will now say HUBSESSED instead of CONNECTEDGTM.
  

• New Ways to Level Up: If you’re looking for even deeper involvement, Hubsessed is launching a new Enterprise tier. This includes all premium newsletter content, plus full access to Attribution Academy courses and a 1-hour quarterly strategy consulting call with Ryan to dig into your specific GTM hurdles.
  

Let us know if you have any questions, we’re here to help make this transition as smooth as possible. And most of all, thank you. It’s been a real privilege to build this newsletter in the HubSpot ecosystem 🧡

– Stuart

Question: Who's the hidden decision-maker that can kill your HubSpot app deal?

Answer: "A lot of times an admin's job is veto more than anything else. They're the guardian of the CRM. If we can build deeply in a way that when they get looped in and look at the screen, they're like, 'yep, looks good to me' - that's all you need."

In this newsletter & podcast episode:

• The journey from HubSpot solutions partner to app developer

• Why most integrations fail to capture value (and how to build differently)

• The hidden power of agency partnerships for bootstrapped SaaS

• Building for the admin: The stakeholder who can veto your deal

• How to validate demand before writing a single line of code

The Built For HubSpot series is presented by Ampersand, the deep integration platform that enables the best startups and AI agents to work seamlessly with platforms like HubSpot without having to manage the complexity and tedious maintenance that comes with integrations at scale.

Why deep integrations win: From agency pain to product solution

Harris Kenny's journey to building OutboundSync started hands deep in agency work: "We were in the portal with the customers, seeing how other apps worked, seeing how apps like Arrows worked, and then comparing that to other apps that we tried where the integrations were just really bad."

The pain point was clear: teams were using tools like Smartlead for outbound campaigns but needed that data in HubSpot for revenue attribution, handoffs, and compliance. The existing solutions? Nonexistent or poorly executed.

"It was like, wow, what is even the point of installing this app at all? And so seeing like, okay, there is a spectrum of quality here. And that's up to the developer to decide what kind of app they wanna build."

What separates a checkbox integration from one that actually drives revenue? Harris learned it's about building for how HubSpot admins actually evaluate apps:

Timeline Events Matter: "There's a lot of stuff that if you build for HubSpot it enables, but it's not obvious."

Forward Compatibility: "Because we integrate in a way that's conscientious of HubSpot's data model, our integration is forward compatible. As new features come out, I'll refresh the UI and be like, 'oh yeah, turns out OutboundSync supports that’”

Build for the Veto: "A savvy HubSpot admin will get it. In a single screenshot, they can see all the integration filter properties and know what they'll be able to do with it."

The HubSpot admin: Your hidden stakeholder

One of Harris's most valuable insights is about who really makes integration decisions:

"An admin, RevOps admin, super admin, a lot of times their job is veto more than anything else. They're the guardian of the CRM."

This persona isn't necessarily your buyer, but they can kill your deal. The solution? Build so deeply that when they review your app, their response is simply: "Yep, looks good to me.”

Why agencies aren't just a stepping stone to growth

While many SaaS companies view agencies as temporary partners that drive pipeline, Harris fundamentally disagrees:

"Some people talk about agencies as like a stepping stone, 'oh yeah, we worked through some agencies, found some traction and now we're moving on.' For us, I fundamentally disagree with that."

The reason? Agencies have superpowers that most SaaS companies can't replicate:

• Specialized Knowledge: They have very specific insights about how things work in their clients portal.

• Access to Power Users: The agencies are general doing the best work, finding the fastest growing companies and iterating their playbook across them.

• Trust Transfer: Agency clients generally trust their recommendations on tooling to achieve the outcomes they want.
  

OutboundSync's agency strategy reveals a counterintuitive truth about ecosystem growth. By partnering with agencies who already understood advanced outbound strategies, OutboundSync could focus on building deep HubSpot functionality rather than educating the market on the outbound maturity curve.

"We eliminated the Smartlead requirement basically. These were companies wanting to move up that outbound maturity curve to level three or four, having multiple domains, using multiple data providers, using AI and dynamic personalization."

Bootstrappers mindset: Singles and doubles

Harris's transition from agency owner to app developer meant confronting harsh economic realities:

"I was running my solutions partner agency where I'm getting HubSpot implementation projects, multiple month, four to five figure contracts. So then to be like, 'okay, well now I'm gonna go try to sell a single seat of OutboundSync for a couple hundred dollars a month'... it was really difficult."

The solution? A Moneyball approach:

"We're hitting singles and doubles. We're not swinging for the fences. When we write code, it needs to work. When we write docs, people need to read 'em. When we onboard someone, we wanna retain that customer."

The most powerful validation of demand came from unexpected user behavior:

"We found users were using HubSpot's Salesforce data sync to get the data into Salesforce. I got a customer service ticket with a screenshot of a contact record in Salesforce and they were like, 'Hey, why is this happening?'"

This organic demand, users hacking together solutions to get OutboundSync data into Salesforce validated the need to expand beyond HubSpot.

The Built for HubSpot series explores the stories behind how the best products and companies are winning by going deep in the HubSpot ecosystem. The series is presented by Ampersand, the deep integration platform that enables the best startups and AI agents to integrate seamlessly and scale fast.

Question: What's the most critical thing HubSpot ecosystem partners need to focus on right now?

Answer: If you're not thinking about how Customer X or Industry Y can leverage AI to transform and grow, you're not doing your job. If you're not obsessing about where things are headed on behalf of your customers and prospects, that's a problem.

In this newsletter & podcast episode:

• Why clearly defined missions ultimately drive ecosystem scale

• Lessons from scaling ecosystems at AWS and HubSpot

• The urgent AI transformation window for HubSpot partners

• Evolving from "doing work" to "designing systems"

• The critical value of partners to a growing ecosystem

The Built For HubSpot series is presented by Ampersand, the deep integration platform that enables the best startups and AI agents to work seamlessly with platforms like HubSpot without having to manage the complexity and tedious maintenance that comes with integrations at scale.

"Meaning Matters": A foundation for scale

Why your mission ultimately determines ecosystem success

Brian shared a lesson that's carried through his journey from AWS to HubSpot to Profoundly: "I really believe that meaning matters. And what I mean by that is like an organization's mission really makes a difference. It's deeper purpose, it's reason for being and so on."

This isn't about feel-good corporate culture, it's about defining your “why” so your customers, partners, and team know where you’re trying to launch the rocket to:

"I think that really has an impact on the organization's ability to truly scale. I think that's because people do their best work when they can identify with what it is that the underlying platform and organization is attempting to accomplish."

Brian’s personal Mission Examples Across Ecosystems:

• AWS: Transforming cancer research through cloud compute power

• HubSpot: The "helping piece" in helping millions of organizations grow better

• Profoundly: Helping customers and experts thrive together

The takeaway is clear: when people see themselves in the mission and understand their personal "why," it drives the commitment and creativity needed for massive ecosystem scale.

Companies Don't Scale. Ecosystems Do.

Brian's second lesson challenges how most companies think about growth:

"Companies don't scale, in my opinion. The platforms that grow exponentially are the ones that really go out of their way to empower others to build on top of them."

At AWS, this meant asking interview questions like "How have you changed your industry?" to find partners who could think at ecosystem scale. At HubSpot, it meant recognizing that partners drive innovation and retention well beyond the initial deal and building internal programs to support them.

What makes ecosystem partners uniquely valuable is their depth of focused:

"When we would go out and recruit industry experts, they knew every crevice of that industry. They knew the metrics that mattered. They knew how to speak that language... somebody incredibly bright waking up every day and ending every day obsessing about what's gonna happen in an industry."

This level of deep industry focus is almost impossible for any single platform with aspirations of hyper growth to replicate across multiple industries and segments simultaneously.

Beyond pipeline: The true value of ecosystem partners

Brian revealed that the biggest unlock at HubSpot wasn't just recognizing partners as lead sources, but understanding their broader impact across the customer journey:

"It wasn't until the organization said, oh, partners are about more than sourcing opportunities. They get customers using what they bought, optimizing their investments, growing, identifying new ways to leverage HubSpot."

Partners as aggregators of customer sentiment

Even more valuable:

"Partners were aggregators of customer sentiment and customer needs. If you talk to one partner, it's like talking to dozens of customers because they're talking to customers each and every day."

This aggregation of insights and context across clients means partners can often articulate customer needs more effectively than customers themselves, helping platforms understand what to build next.

The AI transformation opportunity

Brian delivered an urgent PSA about AI's impact on the HubSpot ecosystem:

"I hope everyone is paying attention... I'm shocked every day at the customers that I talk to who are not using it. I don't even know how that happens at this point."

For partners, there's a brief opportunity to help companies adapt:

"There's this opportunity for partners and experts right now to be one of the organizations that helps those customers rethink things like workflows and building agents and embedding AI into their daily operations... but I don't think that that's measured in years."

The reason? AI will soon make much of traditional implementation and configuration work intuitive and automatic.

From "Doing Work" to "Designing Systems"

The fundamental shift for partner value

Brian outlined the most significant change facing HubSpot ecosystem partners:

"The ecosystem's gonna have to evolve and figure out if that's (implementation) not what customers are gonna need anymore, how do I refactor for what they need? And so I think it's gonna be more about going from doing the work like we had, right? Do it for me, sort of services to how do you design the systems that do the work for the customer forever?"

This shift from execution to system design represents a fundamental change in how partners create and capture ecosystem value.

The AIOps evolution

DevOps for the AI Era

Brian drew parallels between the current AI transformation and the cloud and elastic compute transformation he witnessed at AWS:

"I remember at AWS when the concept of DevOps kind of emerged... Being in the room when those concepts were flushed out in frameworks and like how transformative it was... refactoring for the cloud and now like refactoring for AI."

Brian sees "AIOps" (referenced in a recent Dharmesh Shah post) as the next framework for how organizations structure teams to scale with AI tools. An evolution of RevOps that puts revenue leaders who understand the business context, their customers, and AI as a trusted authority for growth.

Three strategic imperatives for HubSpot Partners

Based on Brian's ecosystem experience:

1. Get Clear on Your Why

Organizations with meaningful missions scale exponentially because they inspire the best work from people who can see themselves in the purpose.

2. Help Customers Refactor for AI Right Now

If you're not obsessing about how AI is transforming your customers' industries, you're failing at client service. This window won't last long.

3. Evolve from Execution to System Design
The future of partner value is designing systems that work forever, not doing repetitive work that AI will soon automate.

Takeaways for the HubSpot ecosystem:

• Meaning-driven missions are strategic advantages, not just culture initiatives

• Ecosystem partners succeed through deep industry obsession that platforms can't replicate

• AI transformation is urgent—partners must help customers adapt now or lose relevance

• The shift from "doing work" to "designing systems" is fundamental to future partner value

• Good client service in 2025 means obsessing about customers' AI transformation

The Built for HubSpot series explores the stories behind how the best products and companies are winning by going deep in the HubSpot ecosystem. The series is presented by Ampersand, the deep integration platform that enables the best startups and AI agents to integrate seamlessly and scale fast.

Question: Is it better to build a standalone product or integrate deeply with HubSpot's platform?

Answer: Where are your users doing their work multiple hours per day? And can you ergonomically meet them there? If that is in the CRM, then strongly consider that. Do it because it's better for the customer. Do not build in a platform like HubSpot or Salesforce with the expectation that it's a magic unlock for distribution.

In this newsletter & podcast episode:

• The strategic decision to build deeply for HubSpot vs. a standalone product

• Why betting on a platform isn’t only about your product

• The myth of "marketplace distribution" and the reality of ecosystem partnerships

• How AI is changing the CRM landscape and integration strategies

• Best practices for evaluating if a deep platform integration the right play

The Built For HubSpot series is presented by Ampersand, the deep integration platform that enables the best startups and AI agents to work seamlessly with platforms like HubSpot without having to manage the complexity and tedious maintenance that comes with integrations at scale.

"Going Deep: Why Arrows bet on HubSpot"

The Big Decision: Product-First or Platform-First?

Three years ago, Arrows made a bold decision that dramatically reshaped the business: “We launched in the HubSpot marketplace for Arrows, and we made a big bet to delete a big chunk of Arrows and focus on the CRM.”

This wasn't just adding an integration, it was reimagining their entire product and go-to-market strategy around HubSpot's platform. Instead of building a standalone product that pulled data from HubSpot, Arrows decided to build a collaborative layer on top of HubSpot that enhanced what users were already doing.

“We really were looking at the product we had built and wondering if we built it today from scratch, how would we build it? And we realized it would be a very CRM-centric, CRM-first product.”

This choice forced difficult tradeoffs:

• Deleting the Salesforce integration

• Removing dashboards and standalone features

• Rebuilding core elements to work natively within HubSpot
  

The "Better Together" strategy

What made this approach successful wasn't just technical integration, it was creating a narrative where Arrows and HubSpot were better together than either product alone.

“What is the unique value we provide? Arrows is the collaborative space for your customers. We don't need to manage any of the commodity data layer, consolidating all the activity and email communications and reporting and automations layer. We don't need to build all of that. That is done very, very well by the CRM, specifically HubSpot.”

By focusing on collaboration, something HubSpot doesn't natively offer Arrows has been able to build a complementary product that solves a specific painful problem while leveraging HubSpot's existing strengths.

"Most people still wouldn't want to log into Arrows for that. I am the CRO, I'm the CEO, I'm the VP of success. Where do I want to go look at reports about what's happening in my onboarding process? I'm gonna wanna look at the CRM."

The distribution myth vs. reality

One of the most surprising revelations from Daniel was about distribution expectations versus reality:

“I think our expectation, and it's still true, was that there would be a stronger distribution within the platform. Most of our distribution comes from doing marketing kind of outside of the platform, outside of the app marketplace.”

The hard truth: HubSpot just does not have a mechanism to match the customers that are using HubSpot for onboarding with an app like Arrows that would make that more valuable to them.

Three key questions to ask before building for HubSpot

Based on Daniel's experience, here are the critical questions to consider:

1. Where do your users spend their time? Where are the actual users doing their work most of the time, multiple hours per day? And can you ergonomically meet them there? A native integration can mean less clicks, less tabs, and deeper adoption.
   

2. Will the depth of your integration create better customer outcomes? Do customers need the UI your product provides to receive value or are they better served to continue using the tools they already know and gain new capabilities through your integration.
   

3. Are you betting on distribution or increased customer value? Do not build in a platform like HubSpot or Salesforce with the expectation that it's a magic unlock for distribution.
   

AI in the HubSpot ecosystem: Reality vs. Hype

Daniel offered a grounded perspective on AI's current state in the HubSpot ecosystem (with a lot of perspective from building with AI at Arrows):

“The marketing is far ahead of the capabilities of the product in terms of AI and agents. The talk about it is far ahead of what's possible and what people are actually doing.”

When asking teams what AI tools they're actually using day-to-day:

• Call recorders with AI note summaries

• ChatGPT for writing assistance

• Limited use of AI assistants for specific workflows

The real opportunity isn't in flashy AI features but in embedding AI capabilities directly into existing workflows:

“Most people don't care about AI necessarily. They'd like to use it more, but I just want to do my job better, get the outcome better. I want it to be easier. I don't want to think about the query. I don't wanna think about the prompt, and I don't want to think about refining it. I just want the result.”

Deep integration bets that change company culture

A fascinating insight from the conversation was how going all-in on HubSpot changed every aspect of Arrows as a company:

“Every aspect of our company understands CRM, how to use it pretty well. What's possible, what's capable, the pros and cons of the data that's accessible, how you would set up reports and workflows and pipelines, and how do you demo around it and do content around it. And that just filters through everything we create and put out there.”

From product development to sales demos to marketing content, the deep integration with HubSpot shapes how the entire company thinks and operates.

Takeaways for building in the HubSpot ecosystem

Whether you’re a founder, product leader, or ops team considering tooling:

1. Focus on customer workflows first, meet users where they already work

2. Don't expect magical distribution, partnerships require long-term investment

3. Consider the "better together" narrative, how does your product enhance HubSpot?

4. AI should solve real problems, not just be a marketing checkbox

5. Be prepared for organization-wide impact—a deep integration strategy affects every department

The Built for HubSpot series explores the stories behind how the best products and companies are winning by going deep in the HubSpot ecosystem. The series is presented by Ampersand, the deep integration platform that enables the best startups and AI agents to integrate seamlessly and scale fast.

Throughout the series, we'll dive into the stories behind how those solutions came to be and how the companies building them are winning by going deep in the HubSpot ecosystem.

The Built For HubSpot series is presented by Ampersand, the deep integration platform that enables the best startups and AI agents to work seamlessly with platforms like HubSpot without having to manage the complexity and tedious maintenance that comes with integrations at scale.

For HubSpot users, this means discovering tools that feel like natural extensions of the platform they already love. For founders and product teams, it means a blueprint for standing out in an increasingly crowded marketplace.

Join me as we explore the companies and innovators who understand what it truly means to be Built for HubSpot.

Find the show on Apple Podcasts, Spotify, YouTube, and all your favorite players.

Back at Inbound 2022, HubSpot CEO Yamini Rangan introduced the connected customer platform, a vision that you could bring your entire customer journey into HubSpot. Fast forward to 2025 and HubSpot has made huge strides in that direction.

But there's always been a fundamental challenge when you’re trying to run a connected go-to-market motion:

HubSpot simply doesn't (and likely can’t) have ALL the context GTM teams need to make the most strategic decisions.

While the app marketplace and custom integrations solve part of the problem, they've always been limited by the rigid and structured nature of APIs and HubSpot’s data model, requiring you to know specific schemas and configure your CRM precisely.

This week, HubSpot released a new beta that changes this integration paradigm.


MCP (Model Context Protocol) - a bridge that allows LLMs like Claude to directly access and modify your HubSpot data through natural language conversation.

HubSpot has moved remarkably quickly to release their MCP Server, and I'm genuinely excited to see what it enables for go-to-market teams, so that’s what we’re digging into today.

This edition of ConnectedGTM was kindly supported by:

Your deal room shouldn't just look good, it should do the work. Flowla 2.0 turns static sales rooms into dynamic workflows that improve prospect experience and remove sales rep busy work.

Book a demo with the Flowla team to see the workflows you could build for your team.

Understanding MCP: The universal language to connect your tools with AI

Most companies are building GTM stacks that are disconnected by default. Even if you’re using best in class integrations, you can’t engage with ALL your integrated data through one pathway.

If you’re trying to use the power of AI to reason and analyze your data across sources you’re likely battling:

❌ Constant context switching as you jump between data and AI tools
❌ Outdated (or unverifiable) information as AI can't access your real-time CRM data
❌ Manual data entry when adding AI-generated insights back into HubSpot

What if your could talk directly to your HubSpot data and combine it with research from the public web (via AI Agents) and any other data source you like using an LLM, without you having to copy/paste or build complex integrations?

MCP is fundamentally different way to connect and engage with data, it isn’t limited by the constraints of traditional integrations:

• Rigid API requirements and specific data formats

• Complex authentication and permission management

• Technical knowledge needed to build and maintain connections

• Point-to-point integrations that don't scale easily
  

So what exactly is MCP?

MCP is an open standard that enables AI systems to communicate with software applications through a consistent language. In simple terms:

Think of MCP as a special mail service for robots 🤖

The AI is like a kid who writes a letter, and MCP makes sure every different system (like a library, a game, or a school database) can read that letter and answer back.

This way, the LLM can get answers or do things in lots of places using one simple mailbox system instead of many complicated ones.

By breaking down data silos, MCP helps advanced AI models give better, more relevant answers because they can fetch up-to-date facts and context.

How to connect to the HubSpot MCP server (plus a practical workflow example)

Let's walk through both setting up the MCP connection with an example of how to use this new connection to analyze our closed-won deals and generate a CRM verified segment and campaign idea.

Step 1: Create a Private App in HubSpot

1. Log in to your HubSpot account, navigate to Settings → Integrations → Private Apps and Click "Create private app"

2. Fill in the basic information:
   → Name: "MCP Access"
   → Description: "Connects HubSpot to Claude via Model Context Protocol"

3. Configure auth by selecting the necessary scopes:

   • Contacts (Read, Write)

   • Companies (Read, Write)

   • Deals (Read, Write)

4. Create the app and copy your access token

💡 Security Tip: For initial testing, grant limited read-only permissions first. You can expand to write permissions once you're comfortable with how the system works.

Step 2: Connect Claude Desktop to the HubSpot MCP Server

1. Install and open the Claude Desktop app and click on settings and in the app toolbar (at the top of the screen not inside the app) click “Settings”

2. Select "Developer" in the left sidebar and then click “Edit Config”

3. This will open a JSON file on your computer “claude_desktop_config.json”. Paste the following code including your HubSpot access token from step 1 into that file.

{
  "mcpServers": {
    "hubspot": {
      "command": "npx",
      "args": ["-y", "@hubspot/mcp-server"],
      "env": {
        "PRIVATE_APP_ACCESS_TOKEN": "< YOUR HUBSPOT ACCESS TOKEN >"
      }
    }
  }
}

4. Save the file and you should now see HubSpot and it’s 21 available tools inside of the “Search and Tools” menu for a new Claude chat.

If you’ve made it this far. You’re ready to “talk” to HubSpot.

Example HubSpot Workflow: Deal Pipeline Analysis and Action

Here's a complete workflow demonstrating how MCP lets you combine HubSpot data with external research to build a hyper-targeted outreach strategy:

Discover Common Traits in Your Best Customers

We all want better ways to refine our segmentation and targeting to be able to send the most relevant message so let’s start by asking Claude to analyze recent closed-won deals for patterns:

What are the common traits of my closed deals in HubSpot, research the companies in the last 5 closed won deals to find signals that could be used to create a tightly defined segment with a common acute pain point.

Claude will then:

• Query HubSpot for your recent closed-won deals

• Retrieve all associated company data

• Analyze patterns across company size, industry, technologies used, etc.

• Look for commonalities in the sales notes and interactions

The power of MCP here is that Claude can run multiple HubSpot queries to gather all this data without you having to specify exactly how to get each piece of information, it knows how to navigate HubSpot's data structure.

Once Claude analyzes the HubSpot data, it will present you with:

• Common characteristics of your winning deals

• Patterns in the problems these customers were trying to solve

• The specific pain point that your solution addressed

For example, Claude might discover: "Your last five closed deals were all mid-sized manufacturing companies (100-500 employees) that mentioned 'inventory forecasting challenges' during the sales process.

Now comes the truly powerful part, instead of being limited to just HubSpot data, you can ask Claude to combine what we know from our CRM with other sources of data and build a more in depth understanding of those new customers.

Try prompting Claude:

What would be publicly available signals that a business might be experiencing this kind of acute pain point? Give me 10 to 20 signals and potential sources of the data that I might use to identify them.

Now you can use these recommendations (either directly in Claude with web search turned on), by calling a more specialized MCP connected data source, or by referencing additional data enriched in HubSpot to identify a list of additional companies that match the same profile as your recently closed won deals.

Now what I want you to do is to search HubSpot for a list of 20 additional companies that might meet these same criteria and be currently experiencing the same acute pain as the closed won deals you analyzed.

The result is a highly personalized, pain-focused segment based on a combination of your internal HubSpot data and external research all orchestrated through a simple conversation with Claude.

p.s. If you’re interested in learning more about how you can use AI to identify new segments and send more relevant campaigns in HubSpot I’d love to chat.

Your best customer just churned.

Their health score was green. The product adoption numbers looked solid. Your CSM had regular check-ins scheduled.

Yet somehow, they still left.

This scenario plays out daily. Why? Because companies are building complicated systems that miss what actually matters and don’t help them connect with customers.

A better answer to bloated CS platforms could be sitting in your HubSpot account.

The Customer Success Workspace just got a big update at HubSpot’s spring spotlight has quietly evolved into a system for driving retention that rivals platforms costing 10x more.

"I hated that I had to recommend tools that were $20-30K a year and took months to launch. Now, with the Customer Success Workspace in HubSpot, I have a tool that saves me time on implementation and training while delivering results, with a system that is already in-house and integrated with customer data."

Jeff Kushmerek, Founder, Infinite Renewals

Today, we're exploring how to leverage HubSpot's CS Workspace to transform your post-sale operations, with a special focus on building effective at-risk playbooks to prevent churn before it happens.

✨ What's New in the HubSpot Customer Success Workspace

This year’s Spring Spotlight brought some major changes to HubSpot's Customer Success Workspace, from entirely new features to deeper customization of the existing functionality. Here's a breakdown of the key improvements:

1. Real-Time Alerts and Actions

The new actions section provides immediate visibility into critical customer signals:

• Health Status Changes: Get instant notifications when customers move between health status categories

• Task Management: See due, overdue, and upcoming tasks in one centralized view and more deeply integrate the customer success workspace with HubSpot’s existing task based features.

• New Customer Assignments: Quickly identify accounts newly added to your book of business

Pulling customer data and the action required into one workspace helps avoid things falls through the cracks, allowing CSMs to prioritize their day effectively without constantly monitoring individual records.

2. Service Object ✨

One of the most significant additions is the ability to use the new Service object as a dedicated post-sale tracking tool:

• Customizable Pipeline: Rename stages to match your specific customer journey (Onboarding, Implementation, Value Realization, etc.)

• Required Properties: Customize the properties you need and enforce data collection milestones at each stage of the journey

• Automated Stage Movement: Configure triggers to automatically advance customers through stages

The Service object essentially functions as a free custom object that can help pick up where your sales pipeline ends, creating continuity across the customer lifecycle.

3. Increased customization options

The settings pages for Customers, Services, Revenue, and Health Scores in the Customer Success Workspace provide a lot of options to make the workspace work the way your existing data structure and processes run in HubSpot:

• Object Configuration: Select which objects and properties to use for key functions

• Pipeline Selection: Choose which pipelines appear in your workspace

• Default View Settings: Configure default views for each tab

• Owner Assignment: Define how customer ownership is determined

These settings allow you to align the workspace with your existing HubSpot configuration rather than requiring you to adapt your processes to fit the tool.

The 4 part framework for Customer Success in HubSpot: The Infinite Renewals Approach

When it comes to implementing customer success in HubSpot, Infinite Renewals advocates for a clear, fundamentals-first approach. Based on their work with CS teams, they've identified four core playbooks that deliver the most impact for retention and growth.

"Implementations usually take months because everyone’s trying to do 15 plays they don’t really need…I'm really trying to pull back and start off with a health score, a renewal playbook, a single at-risk play, and a relationship strategy. Then build up from there."

Jeff Kushmerek, Founder, Infinite Renewals

By starting with these core elements, teams can see immediate value in their day-to-day process and metrics while establishing the foundation for more sophisticated approaches as they mature.

Taking a fundamentals-first approach has helped Infinite Renewals clients achieve impressive results, including a helping a company decrease churn by 28% in just three months and drive 85%+ retention rates across their customer base.

Here’s how the 4-part framework works in HubSpot:

1. Health Score Management

Health scoring is your early warning system for retention risks and expansion opportunities.

HubSpot makes it possible to build a health score with:

• Multi-dimensional approach: Combine usage, relationship, support, business outcomes, and financial indicators in one score.

• Segmented scoring: Create different health scores for different customer segments or journey stages

• Actionable thresholds: Set clear trigger points to drive specific interventions using HubSpot’s automation and engagement tools.

"If you have 10 items that are 10 percent, you don't really know what makes a difference. Regardless of the platform when it comes to health score, let's go for big chunks here and see what really makes the difference."

Jeff Kushmerek, Founder, Infinite Renewals

💡 Start with 3-5 dimensions that actually predict retention for your specific business model, then refine based on real outcomes.

2. Risk Management

Effective risk management identifies and addresses issues before they impact renewal decisions:

• Automated detection: Use health score changes to trigger investigation tasks

• Structured intervention: Follow consistent playbooks for different risk categories

• Root cause analysis: Document the underlying issues driving risk signals

• Escalation paths: Define clear procedures for when standard interventions aren't sufficient

⚡️ Set up a simple workflow triggered by health status changes to "At Risk" that creates a task for the CSM to reach out (see how it works in the next section).

3. Renewal Management

Successful renewals don’t happen on the close date, they're processes that begin the moment a customer signs.

• Time-based workflows: Trigger actions at key intervals (120, 90, 60, 30 days before renewal)

• Value documentation: Systematically track and showcase ROI throughout the customer lifecycle

• Stakeholder mapping: Identify and engage all decision-makers well before renewal conversations

• Forecast tracking: Monitor and report on the renewal pipeline to predict revenue

💡 Start your renewal process at least 90 days before the contract end date to allow time for addressing any issues that emerge.

4. Relationship Check-ins

Regular, structured engagement is the foundation of strong customer relationships:

• Segmented cadence: Align check-in frequency with customer tier (monthly, quarterly, bi-annually)

• Structured agendas: Use standardized templates to ensure consistency and efficiency

• Outcome focus: Center discussions on progress toward customer goals and success metrics

• Action tracking: Document and follow through on commitments made during check-ins

⚡️ Create playbook templates in HubSpot for different types of customer meetings to ensure consistent, high-quality interactions.

The beauty of this approach is that it works with the tools you already have in HubSpot, no expensive third-party platforms or clunky integrations required. With the Customer Success Workspace as your foundation, you can build a retention engine that scales with your business and continuously improves over time.

Step-by-step: Build a simple at-risk playbook in the HubSpot Customer Success Workspace

The real power of the HubSpot customer success workspace (and HubSpot in general) when it comes to preventing churn lies in the ability to identify signals and take proactive action.

One of the most impactful ways to do this is by building an automated risk detection and intervention system. Jeff recommends making the HubSpot customer success workspace part of a weekly operating rhythm.

"We run account health meetings like sales teams run pipeline reviews. The job of CS to be a hundred percent clear from my perspective is to protect revenue.

So how do you protect revenue? Every week you get together and you talk about in reverse sort order with your highest yellow is more important than your lowest red, and you're just kinda working your way through that. And when I say highest, I mean by dollar and how much they're paying you per year."

Jeff Kushmerek, Founder, Infinite Renewals

Let's explore how to implement this step-by-step:

Step 1: Set up health score triggers

Health scores are your early warning system, but they're only valuable if they drive action. Here's how to configure your system to notify the right people when a customer becomes at-risk:

1. Navigate to Customer Success Workspace → Settings → Health Scores

2. Configure your health score thresholds (typically 70-85 as "Neutral" and below 70 as "At Risk")

3. Ensure both the numerical score and status properties update automatically

💡 Operator Tip: Instead of creating multiple complex playbooks initially, focus on one simple workflow triggered by health status changes to drive consistent action.

Step 2: Build your at-risk detection workflow

1. Go to Automation → Workflows

2. Create a new company-based workflow

3. Name it "At-Risk Customer Playbook"

4. Set the enrollment trigger:
   → When property value has changed
   → Property: Health Status
   → New value is: At Risk

5. Click "Save" to confirm your trigger configuration

Step 3: Create a CSM investigation task

The first action when a customer becomes at-risk should be a task for the customer success manager to investigate:

1. Add action: Create a task

2. Configure the task details:
   → Title: "Investigate risk factors for [Company Name]"
   → Notes: Include context about what triggered the at-risk status
   → Assign to: Company owner or CS Manager
   → Type: Email
   → Priority: High

This simple task creates accountability and ensures someone is assigned to follow up on every at-risk signal.

Step 4: Design your outreach email template

Create a template for your CSMs to use when reaching out to at-risk customers. The key is balancing concern with value:

Subject: [specific blocker] to [business outcome]

Hi [First Name],

I noticed some recent changes in how your team is using [Product Name] and wanted to reach out to make sure everything is on track to [business outcome].

Specifically, I saw [specific observation about usage/engagement/support tickets] and wanted to discuss how we can help address any challenges you might be facing.

Would you have 15 minutes this week for a quick chat? I'd like to ensure you're getting the value you expect from [Product Name].

Here's a link to my calendar: [Calendar Link]

Best,
[Your Name]

💡 Make sure to include how the specific risk reason will impact their outcomes in the email. Generic check-ins are less likely to get a response than emails that demonstrate you've noticed something specific.

Step 5: Create a guided playbook for the call

Use HubSpot's Playbooks feature to give your CSMs a structured approach to at-risk conversations:

1. Go to Library → Playbooks

2. Create a new playbook named "At-Risk Customer Call"

3. Add these key sections:
   → Opening: Acknowledge the specific risk factors that prompted the call
   → Discovery Questions: Open-ended questions to uncover underlying issues
   → Action Plan: Framework for addressing identified concerns
   → Next Steps: Clear action items and follow-up timeline

4. Configure the playbook to display automatically when viewing at-risk accounts:
   → In playbook settings, select "Show this playbook to users when..."
   → Set condition: Company health status is "At Risk"

This framework gives you a starting point for proactive risk management. As you gather data about the types of challenges your customers face and which interventions work best, you can expand this playbook with more specific branches for different risk categories.

The goal isn't to create complex automations, but to ensure that every at-risk customer receives timely, relevant attention before it's too late.

Today, retention is the foundation of sustainable growth and the HubSpot customer success workspace provides everything you need to build a scalable, effective retention program with the context across the customer journey in one place.

Infinite Renewals brings more than 100 years of combined CS expertise from leaders who have actually built and scaled customer success teams from the ground up.

Jeff and the team have put together an awesome program specifically designed for HubSpot and can help you implement a system that drives real results for your business to reduce churn and protect revenue.

Definitely get in touch with Jeff and the Infinite Renewals team to make sure you have the right playbook in place to make your customers successful.

Become a paid subscriber to receive additional playbooks each month and get access to the archives.

Busy sales reps often spend hours manually creating quotes (hours they could have spent with prospects).

Too often it takes multiple spreadsheet calculations, document configurations, and approval emails only to find the quote needs to be redone, the prospect is kept waiting, and the sales cycle extends by another week.

For businesses using HubSpot there are many Configure-Price-Quote (CPQ) solutions that can transform this painful process into a streamlined, error-free workflow that takes minutes instead of hours.

Most sales teams face similar CPQ challenges:

→ Manual errors and inconsistency: 42% of companies admit they have "no deal-level pricing guidance" for reps, leading to inconsistent pricing and reduced margins.

→ Time-consuming quote creation: Sales reps spend hours creating quotes manually when automation could reduce this to minutes.

→ Approval bottlenecks: Without structured workflows, quotes get stuck awaiting approvals, extending sales cycles unnecessarily. The shift to remote selling has further accelerated CPQ adoption.

But CPQ isn't a one-size-fits-all category, because no two businesses have the exact same requirements, sales processes or product catalogs.

In this guide:

• The state of CPQ in the HubSpot ecosystem: Results from a survey of more than 100 HubSpot users and partners.
  

• Comparing the top 6 CPQ solutions for HubSpot: Each solution has it’s benefits and drawbacks, but how do their HubSpot integrations compare.
  

• How to get the best results from a CPQ implementation: A handy cheatsheet and checklist to make sure you have your CPQ basis covered.

We’ll get into a comparison of HubSpot’s native quoting features with advanced CPQ tools later in this guide. But first, I want to give a callout to the 2 HubSpot elite partners Aptitude8 and RevPartners who have supported this guide and shared their experience managing complex CPQ implementations for HubSpot customers.

Let’s get into it.

The State Of CPQ In The HubSpot Ecosystem

As HubSpot continues to expand upmarket and attract larger organizations with more complex selling processes, the need for sophisticated Configure, Price, Quote (CPQ) solutions has grown. To learn more I surveyed 126 HubSpot customers and partners about their current CPQ usage, challenges, and future plans.

Recommended HubSpot partners for CPQ

Implementing CPQ in HubSpot requires more than just technical knowledge, it demands a deep understanding of sales processes, revenue operations, and critically, change management. Our featured partners bring specialized expertise to ensure your CPQ implementation delivers maximum value.

RevPartners is a HubSpot Elite Solutions Partner that takes a process-first approach to CPQ implementation. They focus on optimizing human and automated workflows to maximize efficiency and compliance.

→ Strategic Solution Selection: RevPartners follows a structured assessment framework to determine the right CPQ solution based on specific client needs. They evaluate complexity levels—from simple tiered pricing that can use HubSpot's quoting tools to guided selling experiences and complex quote documents with PandaDoc.

→ Cross-System Integration: Specialists in bridging systems for organizations where different teams need different access levels. For example, connecting sales teams in HubSpot with implementation teams in PandaDoc to eliminate double data entry and maintain data consistency.

→ Product Library Standardization: RevPartners helps clients transform inconsistent pricing models into standardized tiers and packages, reducing quote creation time and shortening approval cycles—particularly valuable for organizations transitioning from spreadsheet-based quoting.

→ Advanced Document Customization: Their team implements solutions for cases where HubSpot's native quoting is insufficient, such as when quotes need to display complex product attributes (targeting details, specifications, etc.) that aren't supported in standard templates.

→ Implementation Troubleshooting: With deep experience in common integration challenges, they navigate technical hurdles that even vendor support teams may not understand—like field mapping inconsistencies between HubSpot and PandaDoc that can break integrations.

→ Adoption-Focused Approach: RevPartners drives CPQ adoption by connecting implementation to tangible business benefits, particularly by demonstrating the reporting advantages of structured quote data for sales leadership.

Aptitude 8 is a HubSpot Elite Solutions Partner with extensive experience implementing sophisticated CPQ solutions for mid-market and enterprise clients.

Their approach combines technical expertise with strategic revenue operations guidance.

→ Needs-Based Solution Matching: Aptitude 8 evaluates each client's quoting complexity to recommend the right tool—from HubSpot Quotes for basic needs to DealHub for comprehensive requirements—ensuring clients don't overpay for features they won't use.

→ Results-Driven Implementation: Their CPQ implementations deliver measurable improvements, with clients experiencing up to 75% reduction in quote approval time and 30% faster deal closures through process automation and standardization.

→ Product Catalog Optimization: Aptitude 8 excels at organizing complex product offerings, having successfully streamlined 50+ sales packages into coherent product libraries that simplify quoting and ensure pricing consistency.

→ Margin Protection Systems: They implement robust pricing and bundling rules that safeguard profitability, achieving 100% discount compliance for clients who previously struggled with inconsistent pricing and negative margins.

→ Technical Integration Mastery: Their team bridges gaps between HubSpot and specialized CPQ solutions, creating seamless workflows where data flows automatically between systems without manual intervention.

→ Legacy System Transition: Aptitude 8 specializes in migrating organizations from outdated quoting processes (including spreadsheets and disconnected systems) to unified CPQ solutions with minimal disruption to ongoing sales activities.

Comparing The 6 Best CPQ Tools For HubSpot

To help you navigate the CPQ landscape for HubSpot, we've evaluated the leading solutions across key criteria including capabilities, integration, user experience, and total cost of ownership.

As with purchasing any tool, it’s important to consider the total cost of ownership beyond the software price. For CPQ solutions specifically consider these return on investment factors:

1. Time Savings: Calculate hours saved per quote × quotes per month × hourly cost of sales reps.

2. Error Reduction: Estimate the cost of pricing errors and incorrect configurations prevented.

3. Faster Sales Cycles: What is the value of improved cash flow from reduced quote-to-cash time in your business model.

4. Margin Improvement: Impact of controlled discounting and optimized pricing.

5. Scalability: Ability to handle increased quote volume without adding headcount (or onboard reps faster to a streamlined system).

Most organizations I spoke to have found that a well-implemented CPQ solution pays for itself within 3-9 months through efficiency gains, error reduction, and improved sales effectiveness.

HubSpot Quotes

HubSpot's built-in quoting functionality has evolved significantly over the years, now offering a solid foundation for basic CPQ needs. Understanding what's available natively helps determine whether you need additional tools.

💪 Core Capabilities

• Product Library: HubSpot maintains a centralized product catalog with SKUs, descriptions, and pricing that feeds into quotes and deals. Products can be one-time or recurring, and prices can be fixed or user-editable.

• Quote Templates: Sales Hub Professional and above includes pre-built quote templates ("Original," "Basic," and "Modern") that can be customized with your branding. Enterprise users can create custom templates using the design manager with HTML/CSS for advanced customization.

• E-Signature: Quotes can be sent to customers for electronic signing, with legally binding signatures.

• Payment Collection: In supported regions, HubSpot Payments (powered by Stripe) allows customers to pay invoices online directly from quotes, supporting credit cards and ACH payments.

• Approval System: Sales Hub Enterprise includes a basic approval system where quotes can be set to require manager approval before being sent to customers.
  

❌ Limitations

• Pricing Logic Limitations: HubSpot's native quoting doesn't support sophisticated pricing rules like volume discounts, tiered pricing, or conditional pricing based on customer attributes.

• Basic Approval Workflows: The approval system is primarily an on/off toggle without multi-tier approvals or conditional routing based on deal characteristics.

• No Guided Selling: There's no built-in guardrails or guided selling flow to help reps select the right products or ensure valid configurations.

• Minimal Bundle Support: While you can group products manually, there's no automated bundling or required/optional component relationships.

• Template Constraints: Customizing templates beyond basic branding requires technical skills (HTML/CSS) and is limited to Enterprise tier.

🎯 Best For

• Straightforward products or services with simple pricing models

• Lower quote volume and complexity

• Small sales teams with minimal approval requirements

• Basic document branding needs

🔐 Security & Compliance

• Benefits from HubSpot's security infrastructure and compliance certifications (SOC 2 Type II, ISO 27001, GDPR)

• Permission-based access control through HubSpot's team management

• All data remains within your HubSpot instance

• E-signatures are legally binding and compliant with ESIGN Act

When HubSpot's native capabilities aren't sufficient for your quoting and CPQ requirements several third-party CPQ solutions integrate with HubSpot to provide enhanced functionality. Check out all the options in the HubSpot marketplace.

Here's how 6 of the most popular compare:

quote•hapily is built exclusively for HubSpot and works natively inside the HubSpot experience. It adds powerful CPQ features (pricing rules, approvals, bundles) inside the interface you already use.

📌 Key highlights

✅ Operates completely within HubSpot, no additional logins or context switching
✅ Enables complex pricing rules and approvals while maintaining a native experience
✅ Configures product bundling and calculated pricing using HubSpot products
✅ Fast implementation (typically 2-4 weeks)

📝 Solution breakdown

quote•hapily extends HubSpot's native quoting capabilities with the sophisticated pricing and approval features typically found only in standalone CPQ systems. It keeps both configuration and daily execution in one system, which means faster time to adoption and powerful ways to use your existing HubSpot data across objects.

The solution allows you to create multiple price books for different regions or customer segments, ensuring the right pricing is applied automatically based on deal criteria. For complex product offerings, you can configure bundles with automatic product inclusion, ensuring reps always include necessary items and maintain margin requirements.

👀 What stands out

quote•hapily's deep integration with HubSpot and the inline validation of business process rules means reps never leave the CRM to create quotes, significantly improving adoption rates compared to external CPQ tools.

💪 Key Features

• Price Books: Create dynamic price books for different regions, customer segments, or channels, ensuring the right pricing is applied automatically based on deal criteria.

• Product Bundling: Configure product bundles with automatic component inclusion, ensuring reps always include necessary items and maintain margin requirements.

• Advanced Approvals: Set up multi-level, conditional approval workflows based on any HubSpot data (discount percentage, margin, product mix, etc.).

• Rules Engine: Implement pricing and validation rules to enforce business policies, prevent errors, and maintain consistency across quotes.

• Native Experience: The entire solution operates within HubSpot's interface, meaning reps never have to leave HubSpot to create quotes.

🔥 Integration Depth

quote•hapily is the most deeply HubSpot integrated CPQ:

• Uses HubSpot's UI extensions framework to provide a quote building experience that appears as a native part of HubSpot

• Works directly with all HubSpot objects (deals, products, contacts), eliminating data synchronization issues or delays

• Uses HubSpot's workflow automation features for approvals and notifications

• Leverages HubSpot's existing quote templates and e-signature capabilities

✨ User Experience:

For sales reps:

• No additional login or context switching

• Familiar HubSpot interface with added capabilities

• Guided quote building with validation and automatic calculations

• Visibility into approval status within the deal timeline

For admins:

• Configuration through a HubSpot-like interface (inside HubSpot)

• Rules management through a visual editor (no code required)

• Minimal training needed for HubSpot administrators
  

🔐 Security & Compliance

• Operates within HubSpot's security boundary

• Leverages HubSpot's permission model for access control

• Maintains audit trails of quote creation and approval inside HubSpot

• SOC 2 Type 2 compliant with regular security assessments
  

💰 Implementation & Cost:

• Implementation timeframe: 2-4 weeks

• Pricing: $4,999/year for 5 users, then $49/month for each additional user

• White-glove onboarding $1,000 for standard, $2,500 for advanced

✅ quote•hapily is best for

• Organizations committed to HubSpot as their primary CRM

• Teams wanting to minimize system complexity and additional user training

• Mid-market companies with moderate to complex pricing needs

• Businesses requiring approval workflows and pricing enforcement

PandaDoc

PandaDoc CPQ for HubSpot is a native Configure, Price, Quote solution built for growing businesses that use HubSpot. It accelerates deal cycles by empowering reps to generate quotes and execute contracts without leaving HubSpot and combines document automation, guided selling, and e-signature in one platform.

📌 Key highlights

✅ Creates highly customized proposals with drag-and-drop editing and rich media
✅ Includes powerful e-signature with audit trails and optional payment collection
✅ Tracks when customers view proposals and which sections they engage with
✅ Maintains a library of pre-approved content blocks sales reps can easily include

PandaDoc connects with HubSpot through its marketplace integration to create an end-to-end document creation and signature workflow.

📝 Solution breakdown

PandaDoc combines document automation, CPQ features, and e-signatures into one platform. While not a dedicated CPQ system, it fills the gap for organizations that need to create professional quotes and proposals that close faster.

Its interactive pricing tables allow customers to select options or quantities within the document with automatic price calculation. The platform's analytics track when customers view proposals, which sections they spend time on, and when they sign, giving sales teams unprecedented insight into prospect engagement.

👀 What stands out

PandaDoc CPQ for HubSpot stands out by combining guided selling with powerful document analytics. Sales teams can create standardized quotes within HubSpot while gaining insight into prospects engagement with the proposal, seeing which sections they review to allow more targeted follow-up conversations and faster deal cycles.

💪 Key Features

• Document Customization: Create highly customized proposals with drag-and-drop editing, rich media, and conditional content based on deal attributes.

• Guided selling: Build quotes inside HubSpot with PandaDoc’s UI card selling experience in HubSpot deals (Enterprise CPQ plan only)

• Content Library: Maintain a library of pre-approved content blocks (product descriptions, terms, case studies) that reps can easily include in proposals.

• E-Signature & Payment: Built-in electronic signature with audit trails and optional payment collection capabilities.

• Interactive Pricing Tables: Allow customers to select options or quantities within the document, with automatic price calculation.

• Document Analytics: Track when customers view proposals, which sections they spend time on, and when they sign.
  

🔥 Integration Depth

PandaDoc CPQ for HubSpot offers an embedded quoting experience.

• Generate quotes directly within HubSpot without switching contexts

• Use HubSpot UI cards to ensure quote accuracy and standardization in a guided selling experience

• Two-way integration ensures all data remains synced between systems in real-timeSeamless guided selling experience in HubSpot UI cards

• Pull contact, company, and product data from HubSpot into PandaDoc documents

• Updates HubSpot when documents are viewed, signed, and completed

• Attaches signed documents to the HubSpot timeline

✨ User Experience:

For sales reps:

• Modern, intuitive document editor

• Start from templates that automatically populate with HubSpot data

• Real-time notifications when prospects interact with documents

• Mobile app for on-the-go document management

For administrators:

• Template designer for creating professional document layouts

• User permission management across templates and documents

• Analytics dashboard for tracking document performance

• Integration configuration through PandaDoc's admin panel
  

💰 Implementation & Cost:

• Implementation timeframe: 2-6 weeks depending on template complexity

• Pricing: Business plan starts at $49/user/month. For CPQ, Enterprise tier with CPQ feature add-on is required. Typically $149/user/month.

• Additional implementation services may be required for complex templates

• Premium onboarding available at additional cost
  

🔐 Security & Compliance

• SOC 2 Type II certified with encryption for data at rest and in transit

• GDPR, HIPAA, and ESIGN/UETA compliant

• Comprehensive audit trails for document history

• Advanced access controls and user permissions

• Digital signature certificates with validation
  

✅ PandaDoc is best for:

• Sales teams that value highly customized, visually impressive proposals

• Growing businesses using HubSpot as their primary CRM

• Revenue Operations leaders looking to standardize the quoting process

• Sales teams wanting to accelerate deal cycles with guided selling and approvals

• Organizations wanting to manage their sales process without leaving HubSpot

DealHub CPQ

DealHub offers a comprehensive CPQ platform with an emphasis on guided selling, collaborative deal spaces, and a complete "quote-to-revenue" approach.

📌 Key highlights

✅ Creates personalized DealRooms for buyers and sellers to collaborate
✅ Guided selling playbooks that ensure accurate product selection and pricing
✅ Integrates CPQ, CLM, and subscription management in a unified platform
✅ Provides advanced rules engine for sophisticated product and pricing rules

DealHub CPQ is a comprehensive solution that integrates with HubSpot to streamline the entire quote-to-cash process.

📝 Solution breakdown

DealHub stands out with its unique DealRoom—a personalized digital space for each opportunity where buyers and sellers can collaborate on proposals, configure options, and finalize agreements. This creates a premium buying experience that accelerates deals and improves win rates.

The platform's guided selling playbooks walk reps through the configuration process using interactive questionnaires, ensuring accurate product selection and pricing even for complex deals. It also includes contract lifecycle management capabilities, allowing teams to generate and manage contracts from the same platform.

👀 What stands out

DealHub's DealRoom provides a collaborative buying experience that many other CPQ solutions don't offer. Buyers can interact with proposals, select options, communicate with sales reps, and sign agreements all in one branded digital space.

💪 Key Features

• Guided Selling Playbooks: Interactive questionnaires that guide reps through the configuration process, ensuring accurate product selection and pricing.

• DealRoom: A personalized digital space for each opportunity where buyers and sellers can collaborate on proposals, configure options, and finalize agreements.

• Contract Lifecycle Management (CLM): Generate and manage contracts from the same platform, with approval workflows and redlining capabilities.

• Subscription Management: Handle complex subscription pricing, renewals, and amendments within the platform.

• Advanced Rules Engine: Configure sophisticated product and pricing rules to handle even the most complex scenarios.
  

🔥 Integration Depth:

• Embedded access from HubSpot deals

• Bi-directional data synchronization

• Quote and contract data written back to HubSpot

• Additional integrations with ERP, billing systems, and other platforms
  

✨ User Experience:

For sales reps:

• Guided configuration through interactive playbooks

• DealRoom for buyer collaboration and engagement tracking

• Mobile-friendly interface for accessing deals on the go

• Comprehensive view of the entire sales process in one place

For administrators:

• No-code configuration for product rules and pricing

• Visual workflow builders for approval processes

• Template management for documents and playbooks

• Robust reporting and analytics capabilities
  

💰Implementation & Cost:

• Implementation timeframe: 4-12 weeks depending on complexity

• Pricing: Custom enterprise pricing (typically $75-100/user/month or higher)

• Implementation services often required

• Premium support and success management included

🔐 Security & Compliance

• Enterprise-grade security with SOC 2 Type II compliance

• Role-based access controls with granular permissions

• Secure customer portal with authentication

• Detailed audit logs for compliance purposes

• Support for data residency requirements
  

✅ DealHub is best for:

• Enterprise organizations with complex products and pricing models

• Companies seeking an end-to-end solution from configuration to billing

• Sales teams that value guided selling and collaborative buying experiences

• Businesses with multi-stage approval requirements and complex workflows

Mobileforce CPQ

Mobileforce CPQ is a no-code, enterprise-grade CPQ solution that integrates with multiple CRMs (HubSpot, Salesforce, Dynamics, etc.) with an emphasis on ease-of-use and fast deployment.

📌 Key highlights

✅ Provides mobile and offline quoting capabilities—create quotes anywhere, even without internet
✅ Features no-code configuration for complex pricing rules and product dependencies
✅ Works with multiple CRMs including HubSpot, Salesforce, and others
✅ Offers field service integration for a seamless quote-to-service workflow

Mobileforce CPQ connects to HubSpot while maintaining flexibility for companies with complex environments or multiple CRMs.

📝 Solution breakdown

Mobileforce CPQ delivers enterprise-level CPQ capabilities with a focus on ease of implementation and use. Its standout feature is mobile and offline quoting—reps can create and manage quotes on tablets or phones, even without internet connectivity, with automatic syncing when back online.

The platform's no-code approach allows administrators to configure complex pricing rules and product dependencies through a visual interface, eliminating the need for custom development. This makes Mobileforce particularly well-suited for organizations with limited IT resources but complex quoting needs.

👀 What stands out

Mobileforce's offline capabilities are unique among CPQ solutions, making it ideal for field sales teams working in areas with unreliable connectivity. Reps can configure and quote on-site with customers, even without internet access.

💪 Key Features

• Mobile & Offline Quoting: Create and manage quotes on tablets or phones, even without internet connectivity, with automatic syncing when back online.

• No-Code Configuration: Configure complex pricing rules and product dependencies through a visual interface without custom development.

• Multi-CRM Support: Works with HubSpot, Salesforce, and other CRMs, making it suitable for organizations with diverse or changing CRM strategies.

• Field Service Integration: Connect quoting directly to field service management for a seamless quote-to-service workflow.

• Customer Portal: Optional portal for customer self-service quoting and ordering.

🔥 Integration Depth

Mobileforce CPQ connects to HubSpot while maintaining flexibility:

• Launch Mobileforce CPQ from HubSpot deals (interface does not match HubSpot)

• Synchronize product, contact, and pricing data

• Update HubSpot with quote information and status

• Flexible integration options through the Mobileforce CPQ API

✨ User Experience

For sales reps:

• Dedicated mobile app optimized for field sales

• Offline capabilities for quoting without connectivity

• Guided product configuration based on rules

• Quick quote generation even for complex products

For administrators:

• Visual rule builder for product and pricing logic

• Template management for quote outputs

• User and permission management

• Multi-language and currency support
  

💰 Implementation & Cost:

• Implementation timeframe: 3-8 weeks depending on complexity

• Pricing: Professional tier at $30/user/month; Enterprise at $65/user/month

• Basic onboarding included; additional implementation services available

• Support for custom integration needs
  

🔐 Security & Compliance

• SOC 2 compliant platform with encrypted data storage

• Secure offline operation with encrypted local data

• Role-based permissions and access controls

• Audit trails for quote creation and modifications

• Mobile device security features
  

✅ MobileforceCPQ is best for:

• Field sales teams that need offline quoting capabilities

• Companies with complex product configurations but limited IT resources

• Businesses that may need to support multiple CRMs

LinePilot

LinePilot is a lightweight CPQ automation tool focused on automating HubSpot's line items and simple pricing calculations.

📌 Key highlights

✅ Automates line item creation and pricing calculations in HubSpot with no coding
✅ Freemium model with a very low paid cost structure (per portal, not per user)
✅ Triggers from HubSpot workflows or deal stage changes for seamless automation
✅ Updates existing line items rather than duplicating when templates run again

LinePilot automates the work of creating quotes in HubSpot without requiring users to learn a new system.

📝 Solution breakdown

LinePilot focuses on eliminating the manual work of creating quotes in HubSpot. It's essentially a smart add-on that automates line item creation and simple pricing calculations by leveraging HubSpot's own quoting functionality more effectively.

The tool allows you to define "templates" that specify which products from HubSpot's product library should be added to a deal based on deal properties. It can calculate prices or quantities using HubSpot deal data with basic math and conditional logic in the template rules.

👀 What stands out

LinePilot's automation is nearly invisible to reps. They do what they normally do (fill deal fields, move deal through stages) and the quote lines appear automatically—eliminating tedious manual data entry.

💪 Key Features

• Templates for Line Items: Define templates that specify which products and at what quantities/prices should be added to a deal based on deal properties.

• Dynamic Calculations: Calculate prices or quantities using HubSpot deal data with support for basic math and conditional logic.

• Automated Triggers: Trigger line item creation via HubSpot workflows or deal stage changes.

• De-duplication & Sync: Updates existing line items rather than duplicating if a template run is triggered again on the same deal.

• Multi-template Support: Starter plan allows up to 3 templates, Pro up to 300 templates to handle different quote scenarios.
  

🔥 Integration Depth:

LinePilot is fully HubSpot-centric:

• Uses HubSpot's APIs to manipulate deals and line items in ways that aren’t possible in the UI

• All data remains in HubSpot

• Triggers are based on HubSpot (deal stages or workflows)

• Respects HubSpot's product catalog

✨ User Experience:

For sales reps:

• No new interface to learn—continue working in HubSpot deals

• Move a deal to a stage or click a custom button to populate line items

• Save time and avoid mistakes with automated line item creation

• Edit line items manually after automation if needed

For administrators:

• Simple template setup via web UI

• Define triggers (e.g., pipeline/stage) and product rules

• Create formulas using deal properties to calculate quantities and prices

• No-code and point-and-click configuration

🔐 Security & Compliance

• Customer data stored with encryption at rest in secure environments

• Strict role-based access controls for user permissions

• Regular security patches and updates to protect against vulnerabilities

• Comprehensive audit trails for all system activities

• Full compliance with data protection regulations and GDPR requirements
  

💰 Implementation & Cost:

• Implementation timeframe: Same-day to 1 week

• Pricing: Freemium (20 runs/month), Starter $39/month (300 runs), Pro $66/month (2,000 runs)

• 14-day free trial of Pro features
  

✅ LinePilot is best for:

• Small-to-mid sized businesses using HubSpot who want to streamline quoting without a complex CPQ solution

• Teams with standardized offerings that follow a formula or have repeatable components

• Organizations with limited ops/IT resources that still need to eliminate manual quote errors

GleanQuote

GleanQuote combines CPQ with interactive web proposals in a platform designed for mid-market companies using HubSpot.

📌 Key highlights

✅ Creates interactive proposals (GleanSpaces) with e-signature and payment
✅ Combines CPQ functionality with rich proposal generation in one platform
✅ Supports formula pricing, multi-tier pricing, and conditional pricing rules
✅ Allows buyers to select options directly in the interactive proposal

📝 Solution breakdown

GleanQuote stands out by combining CPQ capabilities with interactive proposals. "GleanSpaces" are personalized web pages where prospects can view proposals, select options, and electronically sign agreements.

Pricing capabilities include formula pricing, multi-tier pricing, and conditional pricing rules, making it suitable for moderately complex pricing scenarios. The platform also features a drag-and-drop proposal builder that makes it easy for sales reps to customize quotes without specialist help.

👀 What stands out

GleanQuote's combination of CPQ and interactive proposals in one platform eliminates the need for separate tools, streamlining the quote-to-close process while still delivering a premium customer experience.

💪 Key Features:

• Interactive Web Proposals: Creates GleanSpaces—personalized web pages for proposals with multimedia content and interactive elements.

• CPQ Functionality: Supports product configurations, bundles, and complex pricing logic for accurate quote creation.

• Customer Self-Selection: Allows customers to select options within the proposal, with pricing that updates in real-time.

• E-Signature & Payment: Built-in electronic signature and optional payment collection for faster deal closure.

• Content Library: Maintains reusable content blocks and templates for consistent proposal creation.
  

🔥 Integration Depth:

GleanQuote provides a bidirectional integration with HubSpot:

• Create quotes from HubSpot deal data using the CRM card (UI does not match the HubSpot interface)

• Sync back completed proposals and signed agreements

• Update deal stages and properties based on prospect engagement

• Pull product and pricing information from HubSpot
  

✨ User Experience:

For sales reps:

• Unified platform for quoting and proposing

• Drag-and-drop proposal builder

• Real-time updates and engagement notifications

• Easy toggling of optional items and pricing recalculations

For administrators:

• No-code setup for pricing rules and product catalog

• Template management for consistent branding

• User permission controls and approval workflows

• Integration configuration through a visual interface
  

💰 Implementation & Cost:

• Implementation timeframe: 2-3 weeks

• Pricing: $55/user/month (5 user minimum) + $2,500 onboarding

• All features included in one pricing tier

• Dedicated onboarding and setup assistance

🔐 Security & Compliance

• 256-bit SSL encryption for all data transmission

• Customer data stored in separate, encrypted databases

• Hosted in secure AWS data centers with redundant architecture

• Daily database backups with comprehensive audit trails

• PCI-compliant payment processing via third-party gateway

✅ GleanQuote is best for:

• Mid-market companies looking for an all-in-one quoting and proposal solution

• Sales teams that need both CPQ functionality and impressive customer-facing documents

• Organizations with moderate pricing complexity but high-value proposals

• Companies that want to enable customers to self-select options within quotes

A Framework For CPQ Implementation Success

Implementing an effective CPQ process takes more than just installing software, you’ll need to map your current process and ensure the system you implemented is adopted by your go-to-market teams to ensure success.

1. Assessment & Planning

• Gather requirements from stakeholders (sales, finance, operations)

• Document current quoting processes and pain points

• Audit existing product and pricing data

• Define success metrics and ROI expectations

3. Configuration & Development

• Set up product catalog and pricing rules

• Configure approval workflows and user permissions

• Create quote templates and output documents

• Integrate with other systems (ERP, billing, etc.)

5. Deployment & Adoption

• Roll out to initial user group or department

• Provide training and support materials

• Monitor usage and address issues

• Gather feedback for continuous improvement

2. Solution Selection

• Evaluate CPQ options based on requirements

• Consider integration depth, user experience, and scalability

• Assess total cost of ownership and implementation timeline

• Select vendor and finalize approach

4. Testing & Validation

• Conduct user acceptance testing with real-world scenarios

• Refine configuration based on feedback

• Train power users and administrators

• Document processes and procedures

6. Optimization & Expansion (Ongoing)

• Analyze performance metrics against baseline

• Identify opportunities for enhancement

• Expand to additional teams or use cases

• Maintain system with regular reviews and updates

The timeline above represents a typical mid-market implementation. Enterprise organizations with complex requirements may need additional time, while smaller businesses with simpler needs might implement faster.

Checkpoint: have you hit these critical milestones

✅ Executive sponsorship: Secure buy-in from leadership to drive adoption

✅ Clean data: Ensure your product catalog and pricing information is accurate before migration

✅ End user involvement: Include sales reps in the process to ensure the solution meets their needs

✅ Change management plan: Develop a plan to transition users from old processes to new systems is the difference between business impact and sunk project cost.

✅ System for continuous improvement: For long term success, it’s important to treat CPQ as an evolving solution, not a one-time implementation.

Implementing changes to the CPQ process for your company is a strategic investment that can dramatically improve your sales efficiency, customer experience, and ultimately your bottom line.

With proper planning, stakeholder involvement, and change management, your CPQ implementation can deliver significant returns through faster quote creation, more accurate pricing, and shorter sales cycles.

A special thank you to our partners

Thee hands-on experience implementing complex CPQ solutions share by the teams at RevPartners and Aptitude8 has been invaluable in creating this guide.

RevPartners brings a process-first approach to RevOps and GTM Engineering. Learn more at revpartners.io.

Aptitude8 combines technical expertise with strategic revenue operations, to deliver measurable impact. Explore their services at aptitude8.com.

Stay tuned for more CPQ-focused content. We'll be diving deeper into specific aspects of CPQ implementation with our partners, in several upcoming live events.

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Messy data isn't just an inconvenience…it's one of the top reasons HubSpot implementations fail to deliver the expected results.

As Casey put it:

"The longer you wait, the messier it gets. If you've been in HubSpot for six days, six months, or six years, the sooner you get data right, the better."

There's nothing worse than discovering your portal has fundamental data issues after you've accumulated thousands of records.

What could have been a simple setup task on day one becomes a massive project that diverts resources from more strategic initiatives.

Today, we're covering Casey's proven 5-step framework for setting up your HubSpot data correctly from the start.

This edition of ConnectedGTM was kindly supported by:

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The hidden cost of messy data

Before diving into the framework, it's worth understanding why data quality matters so much in HubSpot. Poor data structure leads to:

→ Duplicate records that fragment your customer view

→ Missing information that prevents effective segmentation

→ Inconsistent formatting that breaks automation rules

→ Unreliable reporting that undermines decision-making

Bad data directly affects your ability to execute marketing and sales strategies effectively. As Casey called out, even simple tasks like routing leads based on location become challenging when your location data isn't standardized.

"when you don't set it up at the beginning, you have to backfill it all, and it's way harder to backfill than to just have that set up."

Let's explore Casey's 5-step framework to avoid these pitfalls and build a solid data foundation in HubSpot.

Step 1: Standardize location data

Perhaps the most impactful step in Casey's framework is converting free-text location fields to structured dropdowns – particularly for state and country fields.

Why it matters: When location data is entered as free text, you inevitably end up with inconsistencies that make accurate reporting impossible. By converting these fields to dropdowns with preset values, you ensure data consistency from day one.

How to implement:

1. Navigate to Settings → Properties

2. For existing state fields:

   → Clear existing values or create a backup of the data

   → Change the field type to "Dropdown select"

   → Use "Load presets" to add all US states

3. For new implementations:

   → Create a new property named "US State"

   → Set the group to "Contact information"

   → Choose field type "Dropdown select"

   → Load presets for United States states

4. Repeat this process for Country and other location fields

Important: Implement this step before installing data enrichment tools to ensure all enriched data uses your standardized format.

"People have paid me a lot of money to clean this up... I'm going to do this very early in my portal so that I don't have that problem."

When implemented properly, standardized location fields make regional reporting, territory management, and lead routing dramatically more reliable.

Step 2: Create a free domain list to filter leads

One of Casey's first actions in any new portal is creating a list to identify contacts using free email domains (gmail.com, yahoo.com, etc.).

Why it matters: This simple list provides flexibility in how you handle these contacts – whether excluding them from certain campaigns, applying different lead scoring rules, or filtering them from specific reports.

How to implement:

1. Navigate to Contacts → Lists → Create list

2. Name it "Free Domains" and set as an active list

3. Add filter: Contact properties → Email domain → "is equal to any of"

4. Include common free domains: gmail.com, yahoo.com, hotmail.com, aol.com, outlook.com, icloud.com, etc.

5. Create a separate list for test domains (test.com, example.com) to help with database cleanup

"You don't have to use this, you don't have to do anything with this at any point in time. But I always find it to be a really great list to have on hand so I can filter those out as needed."

This list becomes especially valuable when you're trying to identify which contacts might represent legitimate businesses versus individual inquiries.

Step 3: Install a data enrichment tool

With HubSpot Insights sunset on March 17th, every HubSpot portal needs an alternative solution for enriching basic company records automatically.

Why it matters: Data enrichment ensures you have complete company information without manual research. For B2B companies in particular, Casey emphasized that automatic enrichment should be "one of your first installs... it's pretty much a no-brainer."

How to implement:

1. Go to accountscout.app and sign up for a free account

2. From your invite email, click the link and connect AccountScout to your HubSpot portal

3. Add the AccountScout card to your company record view:
   → Settings → Objects → Companies
   → Record customization

   → Add card in the center panel
   → Select "AccountScout"
   → Drag the card to your preferred position

4. Test by adding a new company record, or clicking “Refresh Enrichment” in the AccountScout card on an existing company

Once installed, you can leverage this data for lead routing, segmentation, and personalized outreach without leaving HubSpot.

Step 4: Customize properties that actually matter

While it's tempting to create dozens of custom properties when setting up HubSpot, Casey advocates for a more selective approach.

Why it matters: Excessive properties create confusion, reduce adoption, and increase maintenance overhead. When users don't trust the data, they stop maintaining it, creating a downward spiral.

How to implement:

1. To identify necessary fields ask:

   → What will I collect in forms?

   → How will I segment contacts?

   → Which data points drive business decisions?

2. Create focused, purposeful properties: → Use clear, descriptive names

   → Choose field types that enforce consistency

   → Document each field's purpose

For example, Casey creates a "HubSpot Hubs" multi-checkbox property to understand which products prospects use, which would later inform content personalization.

"Start simple. A lot of people get into a CRM, especially if they're moving from a different CRM, and they just create all the properties... But when you do that you create bloat inside HubSpot."

By limiting your properties to those with clear business value today, you improve data quality and system adoption simultaneously.

Step 5: Import your data correctly

The final step in Casey's framework covers importing existing data without creating duplicates or inconsistencies.

Why it matters: Import errors can introduce data quality issues that plague your system for years. HubSpot's improved import tool offers powerful features to prevent common mistakes.

How to implement:

1. Prepare your import file:

   → Clean data before importing

   → Use column headers that match HubSpot property names

   → Consider downloading a HubSpot example file as a template

2. Use HubSpot's advanced import features: → Start import and select "One file" for cleaner mapping → Choose "Create and update" to prevent duplicates → Map columns to correct properties → Use value mapping for dropdowns → Leverage "Auto-fix errors" for common issues

3. Validate results after import

For state fields in particular the import tool's new value mapping feature is invaluable for standardizing location data from events or other sources where formatting is inconsistent.

By following Casey's framework, you'll build a solid data foundation that supports your marketing and sales efforts rather than hinders them.

As Casey emphasized, investing time in proper setup now saves countless hours of cleanup later. If you want more insights from Casey definitely give her a follow on LinkedIn and join here new HubSpot in 30 cohort.

Most B2B companies are leaking revenue at the most critical moment in the buyer journey: when a prospect requests a demo.

So…RevenueHero requested demos from 1,000 B2B websites. The results were shocking:

→ Only 365 companies responded at all
→ The average response time was 1 day, 5 hours, and 17 minutes
→ By that point, most prospects have already moved on to competitors

Today, I'm breaking down how to build a high-converting demo request process in HubSpot that intelligently routes and schedules meetings without the typical delays and broken handoffs.

This edition of ConnectedGTM was kindly supported by:

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RevenueHero: Intelligent Scheduling and Routing for HubSpot

While HubSpot offers basic meeting scheduling, it lacks the depth of routing customization revenue teams need as complexity and demo volume increase. RevenueHero transforms HubSpot forms into optimized meeting schedulers.

Here's how to determine if you need to go beyond HubSpot's native tools:

Use HubSpot's native tools when:

• You have a small sales team (1-3 reps) without complex territory assignments

• Your routing logic is simple (e.g., everyone goes to the same person or basic round-robin)

• You don't need instant qualification before scheduling

• You have low demo request volume (fewer than 50 per month)

• You're willing to accept manual work for lead assignment and follow-up

For these simpler scenarios, you can:

1. Create a HubSpot form that collects demo requests (and redirect to a default scheduling page on submission)

2. Use HubSpot Workflows to notify the appropriate rep

3. Either automate a follow-up sequence or have reps manually send their booking link via email

Consider RevenueHero if:

• You have a multi-rep sales team with territories or specialized roles

• You need complex routing rules based on account ownership, geography, company size, etc.

• You want instant scheduling immediately after form submission

• You have significant demo volume (50+ requests per month)

• You need to match existing contacts to account owners automatically

• You want to qualify leads before showing available times

• You need detailed analytics on your demo booking funnel

RevenueHero Features

Account-Based Routing

Automatically route leads to the right rep based on account ownership in HubSpot. When a prospect from an existing account requests a demo, they'll be instantly matched with their account owner – providing continuity in the buyer experience.

Dynamic Territory and Round Robin Distribution

Configure sophisticated routing rules based on region, industry, company size, or any HubSpot property. For teams with multiple territories or specialized sales roles, ensure leads are always assigned to the right rep.

Multiple Stakeholder Scheduling

When you have multiple required attendees of a meeting in different roles such as an AE and a solutions engineer, RevenueHero can be configured to check both calendars and only show overlapping availability preventing downstream conflicts and rescheduling.

Instant Scheduling After Form Submission

When a prospect submits your demo form, present them with the assigned rep's calendar. The big advantage of using an integrated demo booking system it’s much easier to use information either directly from the form submission or enriched based on it to route the next step correctly.

No more email ping-pong or waiting for manual assignment – prospects can book immediately while their interest is highest.

Automatic CRM Updates

Every form submission, routing decision, and scheduled meeting is automatically logged in HubSpot. Meeting activities appear on contact timelines, detailed meeting properties are updated on the contact record and ownership is properly assigned – all without manual effort.

One-Click Booking Links

Generate "Magic Links" for email campaigns that automatically pull up the correct calendar based on your routing rules. Include these in nurture emails to make booking frictionless from any touchpoint.

3 questions to evaluate your demo booking process today

As we’ve already established, the bar for responding (and responding quickly) to demo requests is low. When evaluating your own demo request process, consider these three dimensions of speed-to-lead:

1. Speed to assignment - How quickly are leads routed to the right rep?

→ Status quo: 1+ hours for manual assignment

→ Target: <1 minute with automated rules

2. Speed to scheduling - How quickly can prospects book a meeting?

→ Status quo: 24+ hours of email back-and-forth

→ Target: Immediate self-service booking after demo request

3. Speed to response - How quickly do prospects receive personalized follow-up?

→ Status quo: Days of delay (1 day, 5 hours, 17 minutes) or generic autoresponders

→ Target: Immediate confirmation with rep details

For every hour of delay in lead response, you lose approximately 50% of your potential pipeline. By optimizing all three dimensions, you can create a competitive advantage that drives significant revenue impact.

🧠 The 5-Minute Rule: If you can get leads assigned, scheduled, and acknowledged within 5 minutes of form submission, you'll be ahead of 95% of your competitors.

Step-by-step: How to intelligently route and assign leads fast (and book more meetings) 💨

🏆 Goal: Instantly route inbound leads to the right sales rep, enabling immediate scheduling while ensuring no qualified lead falls through the cracks. Fast and accurate lead assignment improves speed-to-lead and provides a prospect centric demo booking experience.

Here’s how to to implement lead routing in HubSpot with RevenueHero step-by-step:

Step 1. Create your demo request form + routing

In RevenueHero, create an Inbound Router and map your website's demo request form to it. Standard HubSpot forms integrate really nicely.

Simply provide the URL of the page with the form – RevenueHero will find it and map the form fields to make sure every submission is captured by RevenueHero and synced to HubSpot in real-time.

Step 2. Define Lead Assignment Rules

Use RevenueHero's Matching Rules to handle known accounts and contacts.

→ For example, create a rule to match leads to an existing account owner if the incoming email domain matches a company in your CRM.

You can choose to match by prospect email domain (RevenueHero will compare the form email's domain to company domains in HubSpot) or by another field like ZIP code or Account ID.

3. Configure a rule based round-robin for new leads

For net-new leads that aren't associated with an existing account, set up a Distribution Rule (round-robin or territory-based assignment) to choose how to route meetings among your sales team.

For instance, create a round-robin rule cycling through your AEs for your "Demo Request" meeting type, or route based on territory/region by adding conditions

e.g. if "Country = USA" assign to the “NAM Sales Team”.

You can add multiple conditions so each prospect is automatically assigned to the correct owner.

If you are using territories, ensure you have a HubSpot contact property for territory or country (this could be pulled from the associated company record if needed using a sync property).

RevenueHero can also read form fields or enriched data to apply these rules.

RevenueHero will automatically assign the contact owner in HubSpot when routing, so the CRM owner reflects the rep responsible.

4. Enable instant scheduling on form submission

Next we want to make sure our demo request flow enables qualified leads to schedule a meeting immediately whenever possible.

RevenueHero enables this with Instant Scheduling that prompts prospects who submit the form with the assigned rep's calendar to book a meeting right away.

💡 To prevent prospects who don't meet your ICP criteria from booking meetings, you could use RevenueHero's Instant Qualification feature or integrate enrichment tools like Apollo or HubSpot Breeze to auto-qualify leads using firmographic data in real-time by embedding hidden fields in your HubSpot form for company size or location, populate them via an API, and use those fields in RevenueHero routing logic.

If not, you might redirect them to a "thank you, we'll be in touch" message instead of the scheduler. HubSpot can store these criteria as form fields (e.g., a dropdown for "Job Title" or hidden fields enriched via integrations).

Set up RevenueHero's router conditions with rules like:

- Employee Size >= 10

- AND Job Title contains "Manager" or "Director" or "VP"

This ensures sales spends time on the best leads and improves the eventual lead-to-opportunity conversion. You can still capture disqualified leads in HubSpot and nurture them differently in an automated sequence.

5. Track demo routing and conversion in HubSpot

Optimizing your demo request conversion rates consistent measurement and tracking. The RevenueHero integration provides plenty of data to build a complete picture of your demo request funnel performance in HubSpot.

Report #1: Demo’s scheduled

📀 Data Sources of "Contacts"
📊 Use the "Vertical bar" chart type:
X-Axis: Meeting Status (from RevenueHero)
Y-Axis: Count of Contacts

RevenueHero categorizes meetings into 5 types based on the status (outcome) - upcoming, completed, not booked, canceled, and no-show. This report breaks down how many of the meetings booked actually happen.

Report #2: Lead Response Time Analysis

Pre-work:

1. Create a contact based workflow
⚡️ Trigger: When an event occurs: Form Submission
→ “Form Name” is any of “Demo Request”

🤖 Action 1: Edit record
→ Property to edit: Contact (current record) → “Demo Requested”
→ Value: Date the action completes

3. Create a custom property “Time to Booked Demo”
→ Type: Calculation
→ Calculated Property Type: Time Between
→ Start Date: “Demo Requested”
→ End Date: “Meeting Create Time”
→ Additional Condition: IF Meeting Type is “Demo" (from RevenueHero)

4. Build the report:
📀 Data Source: "Contacts"
📊 Use the "Vertical Bar" chart type:
X-Axis: Use this to compare any variables you like such as Contact Source, Campaign, Industry, or Location
Y-Axis: Time to Booked Demo

Report #3: Meeting Distribution by Rep

📀 Data Source: "Contacts"
📊 Use the "Bar" chart type:
X-Axis: Contact Owner
Y-Axis: Count of Contacts
Break down by: Meeting Status (from RevenueHero)
Filter: Meeting Type is “Demo" (from RevenueHero)

This report helps you ensure your round-robin or territory-based distribution is working properly and identifies reps who might have unusually high or low show rates.

The key to successful demo request conversion isn't just collecting form submissions – it's creating a frictionless path from interest to conversation by getting leads to the right rep and enabling immediate scheduling, all while maintaining clean and up-to-date HubSpot.

As always, it’s important to test new products with your own workflows and data, so why not try the RevenueHero optimized flow for yourself and request a demo from their awesome team to see it in action.

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Most GTM teams are drowning in data but starving for insights.

Here’s an example:

Wahi's operations team was manually following up on every customer interaction, they were spending 10+ hours weekly just trying to keep up.

Worse yet, by the time they got feedback, it was often too late to act on it.

Today, we're covering how to automate continuous customer feedback collection in HubSpot to drive revenue impact.

We’ll be using Survicate to capture, analyze, and action customer feedback in this post. Let’s get into it.

Survicate has become the most trusted survey tool in the HubSpot marketplace with over 2,000 successful installations and a 97% satisfaction rate. While other feedback solutions force you to leave HubSpot or require complex integrations, Survicate provides a native experience that helps turn feedback into immediate action.

Feedback isn't trapped in another system – it lives exactly where your teams already work in HubSpot. As Chris Eamer from Wahi puts it:

"The ability to trigger contact fields, which can then notify other people based on their responses, was a game-changer."

Survicate Features

Survicate's HubSpot integration enables teams to collect and act on customer feedback without leaving their existing workflows in HubSpot.

Native Survey Embedding in HubSpot Emails

Send surveys directly in HubSpot emails without redirecting customers to external tools or having to ask for their email address again. This means higher response rates and a seamless experience that maintains your brand experience.

Two-Way Contact & Company Record Sync

Automatically enrich HubSpot records with survey responses. Every piece of feedback updates the relevant contact and company properties in real-time, making insights available to use in HubSpot workflows, reporting, email templates, and list-based segmentation.

Workflow Automation Based on Responses

Trigger HubSpot workflows based on survey responses to automate follow-up actions. From routing negative feedback, to identifying advocates for case studies, every response can drive the appropriate action in HubSpot automatically.

Multi-Channel Survey Distribution

Deploy surveys across email, website, and in-product experiences while keeping all data centralized in HubSpot. This creates a complete view of customer sentiment across their entire journey.

HubSpot UI Cards For Survey Results

Survey responses automatically appear in the center panel of HubSpot contact, company, and deal records, making customer feedback instantly accessible to all teams.

→ Sales sees recent NPS scores before renewal calls
→ Support views product satisfaction before helping customers
→ Marketing identifies advocates for case studies
→ Product tracks feature requests by account

AI Survey Analysis

Effortlessly analyze, and act on qualitative feedback using Survicate’s research assistant and research hub to ask questions and organize your data to make smarter decisions faster.

The most effective product marketing strategies are built on consistent and actionable customer feedback. Without it, marketers are operating on assumptions, creating messaging that misses the mark, developing enablement materials that sales won't use, and wasting resources on initiatives that don't move the needle.

To drive revenue impact, product marketers need:

1. More consistent feedback: Regular input across the entire customer journey, from first touch to advocacy

2. More actionable insights: Clear, structured data that can inform messaging, positioning, and sales enablement
   

❌ Without systematic customer feedback collection: you are forced to tradeoff making decisions based on anecdotes or spending countless hours conducting ad-hoc research that quickly becomes outdated.

✅ With systematic customer feedback collection, you can confidently validate messaging, refine positioning, and enable GTM teams with real customer insights that improve win rates.

A structured approach to customer feedback ensures that even as your business grows, feedback systems run smoothly while prioritizing both quantity and quality of insights.

How to continuously test which messaging resonates with your target customers

By combining Survicate's message testing capabilities with HubSpot's segmentation and automation tools. By connecting feedback across multiple touch points, you can validate messaging with specific segments and adjust your communication based on what resonates most.

Let's implement a message test in HubSpot step-by-step:

Step 1. Create your message testing survey in Survicate

Create a "Message Testing" survey in Survicate that includes the following questions.

Introduction: Brief context about why your respondents feedback matters

Question 1: "How would you describe [Product] to a colleague?"
→ Type: Open Text
→ Purpose: Establish baseline understanding before showing variations
→ Optional: Yes

Question 2: "Which of these descriptions best captures what [Product] does?" → Type: Single Select with Rating Scale
→ Options: [Show 3-4 message variations in a random order]
→ Purpose: Core message testing
→ Required: Yes

Question 3: "Why did you choose this description?"
→ Type: Open Text
→ Purpose: Understand reasoning
→ Show if: Any option selected
→ Required: Yes

Question 4: "Which of these benefits matters most to you?"
→ Type: Ranking
→ Options: [List 3-4 key value props]
→ Purpose: Validate value proposition priority
→ Required: Yes

Question 5: "What's unclear or missing from these descriptions?"
→ Type: Open Text
→ Purpose: Identify gaps
→ Optional: Yes

💡 Use Survicate's branching logic to show different message variations based on HubSpot contact properties like industry, company size, or role.

Thank You Message: Use this space to thank your respondents for their participation and link to any incentives you offered, or additional value add resources.

Step 2: Create Your Message Testing Email Template

1. Create an automated email template in HubSpot using the “Simple” template type

2. Add the following content to your email (copy+paste):

Subject: Help shape how we talk about [Product]

Body: Hi {{contact.firstname}},

As someone who understands [industry/challenge], your perspective would be incredibly valuable.

We're working on how we describe [Product/Feature], and we'd love your quick take on a few options:

[SURVICATE EMBEDDED QUESTION]

Your feedback will help us better communicate with others like you.

Thanks, [Signature]

P.S. As a thank you, we'll send you early access to [Benefit/Resource].

Step 3: Send your survey using an automated HubSpot workflow

⚡️ Trigger Criteria: Enroll contacts who:

→ Match your target segment (if you created a list in HubSpot - e.g., Purchasers last 30 days)
→ Have “At least one Survicate: survey answered has all of:
→ “Occurred is more than 30 days ago (EST)

📧 Action 1: Send survey email
→ To: Enrolled Contact
→ Template: Message Testing Email

⏳ Action 2: Delay
→ Delay type: Set amount of time
→ Length of delay: 3 days

🌴 Branch: check the branches in order
→ Send reminder when: At least one Survicate: survey answered has all of:
→ Occurred is less than 3 days ago (EST)

IF: Send reminder

📧 Action 3: Send reminder if no response
→ To: Non-respondents
→ Template: Quick Reminder Email

💡 Tip: Create separate workflows for different segments to test how messaging resonates across different audiences.

Step 4: Analyze your message testing survey in Survicate

Using a dedicated feedback tool for analysis of message testing results makes it easier (and faster) identify patterns and take action. Here's what to look for in your survey data:

Message Clarity
→ Look for completion rates and time spent on message questions
eg. 70% completion rate for Message A vs 45% for Message B

Segment Patterns
→ Analyze responses by role, company size, industry
eg. Enterprise prefers technical message, SMB prefers outcome-focused

Value Prop Alignment
→ Compare stated benefits vs chosen messages
eg. Technical users select feature-focused messages but rank outcomes as most valuable

Red Flags
→ Watch for confusion or negative feedback patterns
eg. "Unclear how this differs from [Competitor]" appearing in 30% of responses

Language Patterns
→ Note specific words/phrases that resonate
eg. "Automated" resonates better than "AI-powered" across segments

Of course the insights you collect from customer feedback are only as valuable as what you are able to do with them. Use these examples to activate your message testing insights with your go-to-market teams.

Understanding your customers isn't just about collecting data—it's about creating a continuous feedback loop that drives real business outcomes. By connecting Survicate with HubSpot, product marketing teams are closing the gap between customer insights and revenue impact.

The path to better customer understanding starts with a single step: implementing systematic feedback collection where your teams already work.

Whether you're looking to validate messaging, refine personas, or measure product-market fit, Survicate's HubSpot integration makes it easy to start collecting insights that drive revenue. Try Survicate for free to start building your feedback engine.

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What happens when someone requests a demo on your website today?

For most B2B companies, it looks something like this:
→ Fill out a form and wait (19% never even respond)
→ Get routed to an SDR (57% of first responses come from SDRs)
→ Schedule a "discovery call" (91% push for discovery vs. actual demo)
→ Maybe see the product... eventually

According to Natalie, and research polling over 2,000 SaaS customers conducted by Navattic and Chilli Piper, the data is clear:

Despite buyers wanting to evaluate products on their terms, only 31% of top B2B SaaS companies make it easy to try their product before talking to sales.

Today, we're digging into how to build a demo experience in HubSpot that actually aligns with how buyers want to buy.

This edition of ConnectedGTM was kindly supported by:

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The Buyer-First Demo Framework

Let's start by evaluating what makes a truly buyer-first demo experience:

There are 3 key criteria successful companies are focusing on:

❌ Accessibility - How quick and convenient is it to evaluate your solution?
❌ Usability - Can buyers get hands-on with your product before a call?
❌ Visibility - Do you provide clear information about pricing and capabilities upfront?

So what can we do instead?

Natalie laid out the playbook she's implemented at Navattic (and seen work consistently across thousands of B2B companies) to implement a demo booking experience that combines:

• Interactive product demos (now used by 31% of top B2B companies, up from 17% last year)

• Automated follow-up (43% now use a combination of automation and human touch)

• Multiple engagement options (varying from quick product tours to detailed feature demos)

Here's how it works in 5 steps:

1. Design for different buying stages and segments - Instead of forcing everyone through the same path, create multiple entry points into your product.

"If you have a very specific ICP, you might just send an automated email. But if you sell to multiple verticals, with different reps assigned to different territories, you need to think about the experience more carefully."

2. Show before you tell - Let buyers explore relevant features before committing to a conversation.

"If a champion wants to go share with other members of their team, they might not need to book another demo. They can just share that interactive demo, for example, if you know your manager only cares about the analytics, we would send just an analytics interactive demo."

3. Personalize pre-demo communication - Don't just send a calendar invite. Share relevant context and examples.

"We see you’re in this specific industry, and say, here's an example of one of our top interactive demos in the same industry, this shows I am an expert. I understand your industry or your use case."

4. Enable your internal champions - Make it easy for your initial contact to share specific features and approaches to how you’ll sole problems with their team.

"By sending them those resources (interactive demos post-call), it can make the entire process more automated and doesn't have to be just a bunch of one-on-one demo calls."

5. Track engagement signals - Use demo interaction data to inform your follow-up strategy.

"We can see specific features they visited. So our reps can go in and say, 'oh, I saw they went through this demo. They clearly care about this feature.'"

Why this buyer-centric demo playbook works

1. Makes product evaluation easy on the buyer's terms

• Prospects can explore independently before committing time

• Sales conversations start from a place of understanding

• Every stakeholder gets relevant information for their role

2. Creates a more efficient sales process

• Enables more relevant personalization

• Gives reps insight into how to best tailor live demos

• Focuses follow-up on areas of demonstrated interest

3. Builds trust through transparency

• Instead of hiding your product behind forms and qualification calls, you can demonstrate confidence in your solution by letting buyers explore freely.

Step-by-step: Building a Buyer-Centric Demo Experience in HubSpot

Let's see how to implement these demo booking principles. Whether you're using interactive demos or not, here's how to create a more buyer-centric experience based on Natalie’s experience:

Step 1: Audit your demo experience for buyer-friendliness

Start by evaluating your current demo request process against these key criteria (if possible recruit a friend or teammate to go through your current process from scratch):

Accessibility: How easy is it to book time with your team?
✅ Calendar scheduling available on website
✅ Response time under 24 hours
✅ Clear next steps in follow-up
✅ Multiple booking options (call, email, chat)

Usability: Can prospects try before they talk?

✅ Interactive product demos available
✅ Self-service exploration options
✅ Feature-specific demos or examples accessible
✅ Easy sharing mechanisms

Visibility: How transparent is your process?

✅ Clear expectations about demo format
✅ Pricing information available
✅ Implementation requirements outlined
✅ Technical documentation accessible

Total Score: x / 12

💡 You don't need to implement everything at once. Start by identifying your biggest gaps and prioritize improvements that align with your buyers' most common friction points.

You can also grade your website and demo follow-up sequence with Navattic’s Buyer First Scorecard.

Step 2: Use automation to reduce time delays in your demo booking experience

These workflows in HubSpot can help support each stage of your demo process - from initial request through post-demo follow-up.

1. Create an automated “Demo Request” Workflow

⚡️ Trigger Criteria: Form submission
→ "Demo Request Form" is submitted

As Natalie called out in our chat, allowing prospects to book a demo directly on your website is the fastest way for them to make progress towards a live demo without the risk of a delayed booking experience playing email tag.

But, that doesn’t mean you have to put your scheduling link directly on the first page they visit on your website. Here are 2 alternative options to consider if you want to vet who can book time on your sales team’s calendar:

1. Use a HubSpot form on your demo booking page to capture information about your prospect that can be used for qualification and routing that then directs prospects to the appropriate calendar to schedule time on submission.
   

2. Use that same form on your website but send your demo scheduling link in an automated follow up email.

Now you have an email address and your prospects have the option to book a demo themselves, we can use an automated workflow to support their progress.

⏰ Add a Delay:
→ Type: For a set amount of time (to give the prospect enough time to schedule in the same session on the next page after the form)
→ Delay for: 20 minutes

🌴 Branch: Check branches in order
→ Meeting Booked: Associated to meeting with known date
→ No Meeting: No match branch

IF Meeting Booked:
✉️ Action 1: Create a task for the assigned rep to send a pre-demo email
→ Template: Industry-specific interactive demo
→ Add pre-demo context and agenda

IF No Meeting Booked:

✉️ Action 1: Send automated reminder email
→ Template: Include industry-specific interactive demo
→ Add pre-demo context and agenda
→ Include sharing options for other stakeholders

2. High Intent Prospect Workflow (if using interactive demos)

⚡️ Trigger Criteria: Demo engagement (with Navattic or other interactive demo tool)
→ Demo Engagement Score > 50
→ Company matches ICP criteria (either in a list or individual workflow filters)
→ No open opportunities

✅ Action 1: Create high-priority task for sales
→ Type: Email
→ Due Date: Immediately
→ Assign Task to: Existing Contact Owner

👥 Action 2: Add to Static List
→ List: LinkedIn demo retargeting audience

📧 Action 3: Enroll in personalized nurture sequence
→ Either use the go to workflow action to send an automated sequence of marketing emails, or use the enroll in sequence action to trigger a 1:1 sequence of touch points across channels from a sales rep.

💡 Keep your initial automation simple. Start with the demo request workflow and add the high intent and post-demo workflows once you've established your baseline process.

The key to improving your demo booking experience is to focus on enabling buyers to evaluate your solution on their terms, while building in the analytics and automation to help your team be more effective.

🕖 Subscribe to get new step-by-step playbooks for implementing a connected GTM motion in HubSpot every Thursday at 7:50am ET / 6:50am CT / 4:50AM PT.

The "next steps" email after a sales call is one of the most critical…

…yet most momentum killing parts of the sales process.

You get off a great demo. You’re excited, the prospect is excited.

But when you send next steps:

→ Your champion doesn't sell your product well internally
→ Important value props and attachments get buried in email threads
→ Stakeholders you've never met (or heard about) kill momentum

Today, we’re covering how to shift your post-demo follow-up from a source of deal friction to a powerful tool for helping champions sell your solution internally.

We'll also be exploring Arrows new AI-powered sales rooms, which connect natively to your sales deals in HubSpot to help reps give buyers everything they need to say yes, without having to spend time managing another tool or opening a new tab.

Highlights

→ Automatically create a single source of truth for every deal at the right time

→ See how Arrows Intelligence proactively suggests updates to move deals forward

→ Create a dashboard to measure the impact of sales rooms on revenue

The step-by-step playbook for building deal momentum with Arrows sales rooms in HubSpot can be found at the bottom of the post.

Arrows is one of the most deeply integrated apps available in the HubSpot marketplace with over 1,200 installs and a 4.9 star rating. While the platform also includes onboarding and customer portal tools, the new AI-powered sales rooms make it easy for sales reps to engage and enable buyers without leaving HubSpot.

"Deals that would take a long time and often got stuck are now moving faster as our champions can gather all the necessary information internally and secure buy-in to proceed."

- Harris Kenny, Founder at OutboundSync

Unlike traditional digital sales rooms that exist as standalone tools, with limited CRM integrations, Arrows provides a native HubSpot experience that enables:

1. Automated room creation using HubSpot workflow actions

2. AI-powered content suggestions from HubSpot data

3. Real-time engagement tracking in deal records

4. Seamless handoff to customer success

5. Complete visibility across the customer journey

Let's look at how Arrows features help turn post-demo follow-up into closed deals...

Arrows Features

AI-Powered Sales Room Suggestions
Most reps waste valuable time manually organizing follow-up materials and updating deals after calls. Arrows analyzes your HubSpot data to automate this process, and:

→ Extract next steps from call transcripts and emails
→ Suggest relevant content based on conversation context
→ Update milestones and value props automatically
→ Create personalized suggestions for each deal
→ Enable quick updating of key properties in HubSpot

One Link For Everything Buyers Need
Lengthy email threads and scattered attachments make it hard for champions to find everything they need to build a cohesive business case and sell internally. Arrows creates a centralized space for every deal to:

→ Organize all deal resources in one shareable link
→ Update content and milestones in real-time
→ Embed your existing enablement materials from your existing tools
→ Provide champions with everything they need to get buy in
→ No login required for prospects

Native HubSpot Integration
Sales tools that live outside your CRM create friction and get abandoned. Arrows lives where your team already works:

→ Create and manage rooms directly from HubSpot deals
→ Automate room creation with HubSpot workflows
→ Track engagement in deal activity timelines
→ Build reports on room performance using synced HubSpot properties
→ Connect the customer experience to HubSpot across the full customer journey with Arrows onboarding plans and customer portals

Track & drive deal momentum

Missing key stakeholders often kills deals in the final stages. Arrows provides complete visibility and tools to keep deals moving:

→ See which stakeholders viewed specific materials
→ Automatically display future meetings and next steps
→ Identify new decision makers automatically
→ Track engagement across buying teams
→ Update HubSpot contacts seamlessly

3 step-by-step playbooks for maintaining deal momentum with Arrows sales rooms in HubSpot

No matter how well your first demo lands, closing the deal relies on maintaining momentum and ensuring every new stakeholder involved clearly understands why you are the right solution to a meaningful problem for their business.

Use these Arrows powered playbooks in HubSpot to:

1. Automate sales room creation at the right point in the buying journey

2. Enable champions with context-aware content and resources

3. Track deal room impact with custom dashboards
   

Not only will you close deals faster, but you'll also gain visibility into how stakeholders engage with your materials - helping you identify and address objections before they derail deals. Here's how they work step-by-step:

Playbook #1: Automate Sales Room Creation in HubSpot

Converting a great first demo into a closed deal requires keeping your champion engaged and equipped with the right resources. By automatically creating a collaborative sales room when deals reach specific stages, you can ensure every prospect gets a consistent, personalized buying experience.

Step 1: Configure your Sales Room template

First, set up room templates in Arrows that align with your sales process and typical customer segments. For example a basic Arrows room template might include blocks for:

→ Core value proposition - tailored specifically to this prospect and the prior conversations.

→ Team - the participants on both sides of the deal who may be interacting in the sales room

→ Next Meeting - an indicator of the next meeting scheduled in HubSpot or an embedded calendar to book if needed.

→ Deal Milestones - a space to outline the steps in the buying process and align around what is needed from who and when.

→ Next Steps - The action that needs to happen to move the deal forward powered by Arrows Intelligence.

💡 Keep templates focused on essential content. Arrows Intelligence will suggest additional relevant resources based on actual conversations.Before you start:

📚 Beyond creating specific templates as a starting point for each room, you can also add content to your block library making it easy to add to an individual room as needed to move a deal forward.

💡 Before you begin, ensure your call recording tool is properly integrated with HubSpot. The quality of meeting summaries synced to HubSpot significantly impacts the AI suggestions you'll receive.

Some popular call recording options that work well with HubSpot include Fathom, Avoma, Fireflies, and Grain.

Step 2: Automated Arrows sales room creation in a HubSpot workflow

Here’s how it works step-by-step:

⚡️ Create a deal-based workflow in HubSpot:

Trigger Criteria: → Deal Stage is any of "Demo"

🤖 Action 1: Use Arrows "Create Sales Room" workflow action

→ Template: “Enterprise Deals” Template
→ Customer Name: {{ deal.dealname }} Sales Room
→ Customer Website: “Company Domain Name”

💡 You may need to add a new data source to your associated data in order to include company properties like “Company Domain Name”

✅ Action 2: Create a task for the sales rep to send a manual follow up email
→ Title: Follow up with { deal.dealname }
→ Type: Email
→ Due: Immediately
→ Notes: Instruct the rep to use the appropriate follow up template
→ Assign To: Deal owner

💡 Your introduction email should clearly communicate the value of the sales room and link to it directly (a visible link is easier to copy + paste to share across channels).

Here's a template you could use:

Playbook #2: Drive Deal Momentum with Deal Room Blocks and Intelligent Suggestions

Beyond a static sales room with content, Arrows Intelligence makes proactive suggestions for what to do next in your sales room based on all the activity and context that builds up in your HubSpot deals.

Let's look at how to use these suggestions to keep your sales rooms current and relevant to prospects at all times.

Step 1: Understanding Suggestion Types

Instead of having to pay attention to every deal all the time, or dig through call recordings and notes in the activity timeline in HubSpot to figure out the best action to take to move the deal forward, Arrows does that work automatically in the background.

Content Recommendations

→ New content blocks based on conversation topics
→ Resources mentioned in calls or emails
→ Case studies relevant to discussed use cases

Milestone Updates

→ Timeline changes from deal notes
→ Next steps from call recordings
→ Close date adjustments

Value Proposition Refinements

→ Updates based on discussed pain points
→ Specific features or benefits mentioned
→ Custom success metrics

💡 The more context you have in HubSpot (calls, emails, notes), the more accurate and helpful the suggestions will be.

Step 2: Make Deal Updates Fast With Intelligent Suggestions

Making sure your team know when and how to make suggested updates to the sales room for a deal is critical.

🛎️ Fortunately, Arrows sends helpful Slack notifications for:

→ New content suggestions
→ Milestone updates
→ New stakeholder engagements

👀 When a new notification is received it’s only a couple of clicks for the rep to:

→ Open the deal record in HubSpot
→ Check the Arrows CRM card
→ Review the suggested changes or updates

⚡️ Take Action:

→ One-click approve relevant suggestions
→ Customize content before adding to the room
→ Decline irrelevant recommendations

Instead of sales reps taking 20-30 minutes after each call to review notes and transcripts before sending a long “next steps” email, they can quickly add the suggested content to the room and send one-link that packages everything the buyer needs.

💡 You can provide Arrows Intelligence with business rules about when to suggest specific content as you add blocks to your library.

Playbook #3: Build a Sales Room Impact Dashboard in HubSpot

Understanding how sales rooms influence your deals is crucial for optimizing your process and accelerating your pipeline. Let's build a dashboard that shows exactly how Arrows sales rooms can impact deal velocity, engagement, and close rates.

Arrows syncs deal properties for:

1. Arrows room URL

2. Arrows room link (html)

3. Arrows room total views

4. Arrows room last viewed timestamp

We can use this data synced between Arrows sales rooms and the HubSpot deal to build reports that connect prospect engagement to revenue impact.

Step 1: Create a Sales Room Performance Dashboard

First, create a dedicated dashboard to track your sales room metrics:

1. Navigate to: Reports > Dashboards > Create Dashboard

2. Name: "Sales Room Performance"
   

Step 2: Build sales room performance reports in HubSpot

Report #1: Days to Close w/ Sales Rooms

📀 Data Sources of “Deals”
🎯 Chart Type: Summary
→ Displaying: “Average” Days to Close
→ Filter: Deal - “Arrows room URL” is known
→ Filter: Deal - “Is Open” is “0”

Report #2: Average Closed Revenue w/ Sales Rooms

📀 Data Sources of “Deals”
🎯 Chart Type: Summary
→ Displaying: “Average” Amount
→ Filter: Deal - “Arrows room URL” is known
→ Filter: Deal - “Is Open” is “0”

Report #3: Total Closed Revenue w/ Sales Rooms

📀 Data Sources of “Deals”
🎯 Chart Type: Summary
→ Displaying: “Sum” Amount
→ Filter: Deal - “Arrows room URL” is known
→ Filter: Deal - “Is Open” is “0”

Report #4: Sales Room Views by Open Deals

📀 Data Sources of “Deals”
📊 Chart Type: Horizontal Bar
→ Displaying: “Deal Name” measured by “Total” Arrows room total views
→ Filter: Deal - “Arrows room URL” is known
→ Filter: Deal - “Is Open” is “1”

Report #5: Sales Room Views by Sales Rep

📀 Data Sources of “Deals”
📊 Chart Type: Horizontal Bar
→ Displaying: “Deal Owner” measured by “Total” Arrows room total views
→ Filter: Deal - “Arrows room URL” is known
→ Filter: Deal - “Is Open” is “1”

Report #6: Sales Room Views by Pipeline Stage

📀 Data Sources of “Deals”
📊 Chart Type: Vertical Bar
→ Displaying: “Deal Stage” measured by “Total” Arrows room total views
→ Filter: Deal - “Arrows room URL” is known
→ Filter: Deal - “Is Open” is “1”

Report #7: Last Activity Date vs Last Room Activity

📀 Data Sources of “Deals”
🍴 Chart Type: Table (Unsummarized)
→ Displaying: “Last Activity Date” and “Arrows room last viewed timestamp”
→ Filter: Deal - “Arrows room URL” is known
→ Filter: Deal - “Is Open” is “1”

💡 Consider adding your sales room reports to your team's default dashboard view for easy access during pipeline reviews.

Keeping deals moving forward after a great first call shouldn't require your champion to dig through email threads or struggle to articulate value to their team. And your sales team shouldn't have to choose between updating the CRM and following up with prospects.

What stands out about Arrows approach is how they've applied AI not just as a flashy feature, but in a way that quietly does the heavy lifting in the background to help sellers do what they do best. The depth of the HubSpot integration also means your team gets intelligent suggestions without changing their workflow.

If you enjoyed these playbooks for Arrows Intelligence powered sales rooms, I'd definitely recommend checking out how teams like OutboundSync and Roobrik are using Arrows to close deals faster while keeping everything centralized in HubSpot.

If you want to try Arrows for yourself you can start a free 7-day trial or book time with the team to see a personalized demo (the Arrows team are all A+ humans).

🕖 Subscribe to get new step-by-step playbooks for implementing a connected GTM motion in HubSpot every Thursday at 7:50am ET / 6:50am CT / 4:50AM PT.

Picture this: You're selling to airlines (there are only ~200 of them in the US), but they won't take your meeting. They think they know what your product does, and no number of “touch points” are getting through.

So what do you do?

If you're Kamil, you map the route to their HQ and put up billboards that say "You think we are X, but we're not X."

Two days later, the prospect emails…

"We saw your billboard. It was hilarious. You're right - let's talk."

That's the power of showing prospects you know them. Not just their {{ first_name }} or {{ job_title }} - you know their actual misconceptions, challenges, and context.

Which brings us to the powerful HubSpot feature hiding in plain sight.

Smart content in HubSpot lets you dynamically personalize your website, landing pages, and emails based on what you know about your visitors - whether they're a brand new lead or a target account deep in your sales process.

But here's the thing - most teams either:

• Don't know this capability exists

• Aren't sure how to implement it effectively, or

• Get caught up trying to personalize everything (and end up personalizing nothing)

Today, we're covering how you can use smart content in HubSpot to create more relevant experiences for your named accounts and contacts without needing to clone dozens of pages manually.

A framework to go beyond { personalization } and become relevant to your buyers

There's a critical difference between personalization and relevance. As Kamil puts it:

"Sometimes it's very obvious that you just put a personalization token in there... it's kind of gimmicky and doesn't really add value."

Let's break down how to use smart content effectively to build relevance that cuts through the noise. First let’s get clear on our options for personalizing content in HubSpot:

1. Token Based Personalization → Using property values directly like name or company.

2. Contextual Relevance → Matching custom content sections to industry, role, or pain points dynamically using smart content.

3. Account-Specific Messaging → Delivering custom experiences for target accounts based on specific account research using smart content.

The goal is moving up this spectrum.

Here’s how to approach using smart content to build relevance in 4 steps:

1. Identify your visitors - Before you can show relevant content, you need to know who's viewing it. We’ll focus on 2 primary ways to identify who’s viewing your content.

→ Use first-party cookies for HubSpot based campaigns
→ Use UTM parameters for ads or external campaigns.

2. Understand the intent - Layer in context about why someone is on your site and what they're trying to accomplish.

• Where they came from (Ad group, previous page, etc)

• What campaign brought them

3. Add Business Context - Pull in everything you know about their situation from your HubSpot CRM:

→ Ad Source (using UTM parameters), Country, Device Type, Referral Source, Preferred Language, Contact List Membership,

• Industry challenges

• Company details

• Technology stack

• Current buying stage

4. Create Relevant Experiences - Use HubSpot's section-level smart rules to show the right content to each visitor:

• Show industry-specific case studies

• Reference relevant pain points

• Display proper technical specs

• Present appropriate next steps

The power of HubSpot's smart content isn't just the ability to swap content based on rules. It's that all your contact, company, and engagement data lives in one place - enabling you to create truly relevant experiences based on everything you know about a visitor.

Like that billboard for the airline - the goal isn't showing different content to everyone. It's showing the right content to the right person at the right time.

For smart content to be most effective you need a strong foundation in your HubSpot account. Try Kamil’s 100+ point HubSpot Audit Checklist to identify what’s missing.

Get Kamil's Checklist

Step-by-step: Create the most relevant landing page experience possible with smart content

The power of smart content in HubSpot lies in its flexibility - you can start personalizing content without complex integrations or developer resources using HubSpot’s landing page builder.

Let's see how to implement smart content personalization by building a simple landing page in HubSpot step-by-step:

Step 1: Design your content structure

Before adding any smart rules, plan your page layout with personalization in mind.

Kamil recommends using a “resources hub” approach that includes educational content to build relevance and trust with prospects making them more likely to engage via email and phone rather than taking a direct response approach.

Here's a few ideas for what to include in each personalized variation of your HubSpot landing page that can take advantage of smart content:

1. Show Recognition - Acknowledge what you know about the visitor to build relevance immediately. When a telecommunications company lands on your page, reference their industry challenges explicitly - "We know telecommunications companies like yours struggle with high-volume data processing."

2. Present Clear Context - Frame your solution in terms of their specific situation. This isn't about generic benefits - it's about showing you understand their unique challenges and how you solve them in their context.

3. Demonstrate Value - Show exactly how you help similar companies succeed. Use customer stories, metrics, and examples that match their industry and use case. The closer the example matches their situation, the more compelling it becomes.

4. Build Confidence - Use social proof that resonates with their context. Don't just show any customer logos - show ones from their industry. Feature testimonials from similar roles. Share case study snippets that mirror their challenges.

5. Highlight Key Features - Focus on capabilities that matter most to the visitors role. A technical buyer needs different information than a business user. Show the details relevant to their situation.

6. Remove Friction - Address common objections before they arise. Be specific about implementation timeline, resource requirements, and success metrics for companies like theirs. Make it easy to envision success.

7. Guide Next Steps - Present a clear path forward based on what you know about them. Show the right call-to-action, connect them with the proper contact person, and offer additional resources that match their interests.

💡 Smart content works at the section level in HubSpot. Design your page with modular sections that can be swapped out dynamically while maintaining the layout.

Step 2: Set up smart rules using HubSpot CRM data

One way to leverage smart rules to display dynamic content is using the data already in your CRM. For example if you want to personalize your content for specific target accounts, you could create rules based on company data:

1. Create an active list of contacts in buying roles at target accounts (or whichever segments you’d like to personalize content for):
   → Buying role “Is Known”
   → Target Account is "Yes"

   

2. Create smart rules for each content section in your landing page
   For each section you want to personalize:
   → Select "Contact List Membership" as the targeting type
   → Choose your target account list
   → Create variations for each industry or account segment

   

3. Add dynamic content elements
   📝 For each variation:
   → Customize headlines using industry-specific language
   → Feature relevant case studies and social proof
   → Display account-specific pain points
   → Show the assigned account owner's meeting link
   

Step 3: Configure ad campaign specific smart rules

To match your landing page content to the content and messaging displayed in your digital advertising you can use UTM parameters to target the ad group level or a specific ad campaign in a HubSpot connected ad account:

1. Connect your ad accounts to HubSpot
   → Connect Google Ads and/or LinkedIn Ads
   → Enable auto-tracking parameter insertion
   

2. Create smart rules based on UTM parameters
   For each ad group or campaign:
   → Select "URL Parameter" as your smart content targeting type
   → Enter your UTM parameter (e.g., utm_campaign)
   → Create variations matching your ad groups
   

3. Customize content for each variation
   → Match headlines to ad keywords
   → Show industry-specific benefits
   → Customize CTAs based on intent
   → Display relevant testimonials

💡 Pro tip: Test your smart rules by previewing the page using different UTM parameters. This lets you verify each variation before going live.

Remember, don’t over personalize and focus on relevance of novelty.

Start small with one or two key sections or segments, measure the impact, and expand based on what resonates with your audience and translates into downstream revenue impact.

I hope this playbook gives you the foundation for creating more relevant experiences with the smart content tools already available in your in HubSpot account.

Check out more of Kamil's playbooks on his YouTube channel or if you’re looking for more hands on help with B2B demand gen and revops I’d personally recommend talking to Kamil and 42 Agency.

🕖 Subscribe to get new step-by-step playbooks for implementing a connected GTM motion in HubSpot every Thursday at 7:50am ET / 6:50am CT / 4:50AM PT.

Running a webinar program that generates pipeline requires more than just scheduling an event and hoping people show up.

Today, I want to share a step-by-step playbook to align your webinar strategy with your marketing and sales efforts in HubSpot.

We’ll be using Contrast in today’s playbooks, a product I first used back in 2023 to run webinars at Arrows. I’m still yet to find a tool where more people ask what it is and compliment the experience.

Highlights

→ Create registration workflows that convert more of your target accounts

→ Build automated follow-up sequences in HubSpot based on webinar engagement

→ Connect webinar data to your sales and marketing reporting

The exact steps to implement all 3 webinar playbooks in HubSpot can be found at the bottom of the post.

Being exclusively focused on HubSpot, Contrast boasts hundreds of customers and delivers an exceptional webinar attendee experience while also reducing the friction between the webinar and your CRM. With a 4.9 rating in the HubSpot marketplace, it's the highest-rated webinar platform.

While other webinar options require manual CSV imports or complex Zapier workflows to sync with HubSpot, Contrast provides a deep integration that enables:

1. Alignment of marketing and sales in HubSpot

2. Creation of consistent branded experiences

3. Capturing actionable engagement data

4. Turning webinars into ongoing content

5. Building a scalable content hub

Let's look at how Contrast's features help connect your webinar strategy to pipeline...

Contrast Features

One-click HubSpot integration with 2-way sync

Most teams waste hours manually updating CRM records after webinars, leading to data gaps and missed follow-up opportunities. Contrast pushes 20+ engagement datapoints to HubSpot in real-time:

→ Updates webinar engagement in the activity timeline
→ Creates and updates contact properties instantly
→ Tracks attribution with registration UTM parameters
→ Automatically adds webinar registrants in workflow actions
→ Never overwrites existing data

AI-Powered Content Repurposing

Webinars contain valuable content but teams often lack the resources to repurpose it effectively, leaving evergreen content opportunities on the table. Contrast turns every webinar recording into weeks of content with AI:
→ Generate clips from key moments
→ Create blog and social posts from your webinar transcripts

“Contrast webinars are our content machine. We milk every webinar now instead of just leaving them on our website. Webinars feed our content calendar for weeks.” – Olivia Oberle Ruiz, Head of marketing at airfocus

Branded and engaging webinar experiences

Generic webinar platforms make your brand look outdated and unprofessional, hurting credibility with prospects. Contrast provides complete brand control:
→ Use your own colors, fonts, and logos
→ Add interactive chat, audience polls, and Q&A
→ Automate and customize pre and post webinar emails

Engagement Analytics

Without granular engagement data, teams can't identify their most qualified leads or optimize their webinar strategy. Contrast provides deep insights:
→ Track watch time and drop-offs
→ Monitor real-time interaction
→ View source attribution
→ Build engagement-based scoring

3 step-by-step playbooks for running webinars that drive pipeline in HubSpot

Ultimately the purpose of a webinar program is to deepen your relationship with prospects (or customers) by building trust and providing valuable education on topics they care about.

Success though will be defined by how effectively it impacts business metrics like pipeline generated and revenue.

Use these Contrast powered playbooks in HubSpot to:

1. Improve lead scoring with webinar engagement data

2. Automate (or don’t) segmented webinar follow up

3. Build a webinar performance dashboard

Here’s how they work step-by-step:

Playbook #1: Use Webinar Engagement In HubSpot Lead Scoring

Not all webinar leads are created equal. By intentionally scoring webinar engagement, you can identify your warmest leads and prioritize follow-up effectively.

Building an effective lead score in HubSpot allows you to continuously monitor key metrics that signal increased intent to buy.

Step 1. Define Your Lead Scoring Criteria

To build an effective scoring model using Contrast's webinar engagement data in HubSpot you’ll need to create workflows for each webinar engagement criteria you would like to include in your lead score.

This is necessary to enable use of the “Enrolled in Workflow” event inside the HubSpot lead score builder. Here are 4 example Contrast engagement triggers you could use:

Webinar Registration: 5 points
→ Triggered when a contact registers for a webinar

Webinar Live Attendance: 10 points
→ Highest value for real-time participation

Webinar Replay View: 8 points
→ Demonstrates active interest

High Engagement Bonus: 5 points
→ Awarded for > 75% live event watch time

💡 When building your webinar engagement score (assuming you chose to build a company score), you'll need to properly configure how individual contact engagement rolls up to the company level.

💡 Consider implementing score decay to maintain accuracy and avoid counting engagement that may not reflect the current situation in an accounts progression.

Step 2. Select the accounts you’d like to score

When implementing lead scoring in HubSpot, strategically choosing which companies to score helps focus on qualified prospects even requiring the combined scoring capabilities only available on enterprise tiers.

💡Use an active list with filters that match your target customer profile to specify the accounts you want to score in the HubSpot lead score builder:

1. Choose "Score specific companies"

2. Add your "ICP Companies" active list

Result:

• Only ICP-fit companies receive engagement scores

• Missing score equals a likely poor fit

• Automatic filtering of unqualified leads

💡 By scoring only companies that meet basic fit criteria, you can use engagement data more effectively to prioritize sales outreach.

Step 3. Organize score properties and thresholds

The final step in configuring your company engagement score is setting thresholds that trigger specific actions from your revenue team. Your company engagement score appears as a property in HubSpot that can be used in workflows, reporting, and on contact records.

HubSpot provides three threshold levels that you should align with your team's follow-up capacity from 1:1 personalized outreach to Tier 1 “hot leads, to automated low awareness and education nurture campaigns.

💡 Set your "High" threshold at a level where your sales team can realistically follow up with every account that reaches it. It's better to have fewer, higher-quality hand-offs than to overwhelm your sales team with ultimately poor fit leads.

Playbook #2: Automate Post-Webinar Follow Up In HubSpot

Converting webinar participants into customers requires a blend of intentional automation and personal outreach.

The chances are, sending the same message to your “in pipeline” prospect who had a demo 2 days ago and has an open email thread with an AE as you send to a first time visitor will not drive the best results.

We can use HubSpot active lists to easily segment our webinar registrants and ensure they receive the best fit follow up strategy.

Here’s how to use filters to create the most important lists to drive your strategy:

• Webinar Registrants with Open Opportunities

• Webinar Live Attendees

• Webinar Registrants Without A Live View

Membership of these lists can then be used as enrollment criteria for workflows and sequences to automatically route webinar registrants and ensure:

• Sales time is spent on the best fit and most qualified opportunities

• No potential leads fall through cracks of missed follow up

• Reporting is more accurate and consistent
  

1:1 Sequence - Engaged ICP Webinar Follow Up

For contacts that meet ICP criteria and showed high engagement, enrolling them in a follow-up sequence that combines automated and manual touches is an effective way to manage the marketing to sales handoff.

Here’s how it works to notify the owner of an open deal where an associated contact engages in a webinar:

⚡️ Create a contact based workflow

Trigger Criteria: Enroll companies when they meet these filters:

→ At least one Contrast webinars: Live watch time has all of:
→ Live completion rate is greater than or equal to 70 AND
→ List membership includes “ICP Account Contacts”

💡 You may choose to replace the live completion rate from the webinar with your lead score reaching a specific threshold and a contact becoming an MQL to trigger your workflow. eg.

⚡️ Trigger the workflow if HubSpot score > 70

🤖 Set the “Lifecycle Stage” property to “Marketing Qualified Lead” or your equivalent

… continue with the remaining workflow steps

🤖 Action 1: Send Slack notification
→ Channel: #sales
→ Message: 💻 {{ contact.firstname }} {{ contact.lastname }} from {{ company.name }} attended more than 70% of the {{ contact.contrast_last_registration }} webinar.

🔀 Action 2: Enroll in sequence (HubSpot enterprise tiers only)
→ Name: Engaged ICP Webinar Follow Up
→ Sender Type: Contact owner
→ Contact Owner: Contact owner

✅ Alternative Action 2: Create a task (HubSpot pro tier)
→ Name: Follow Up With Hot Lead
→ Task Type: Email
→ Assigned To: Contact owner

Providing sales reps real-time insights on how their current prospects are engaging with webinar content gives them both a reason to reach out, and something to say to help move their deal forward.

Automate Nurture Emails (Non-ICP or Low Engagement)

For contacts that don't meet ICP or engagement criteria, consider sending these automated follow-ups using marketing emails in a HubSpot workflow.

1. Resource Roundup: Curated resources mentioned during webinar

2. Social Proof Email: Case studies and testimonials related to the webinar topic

3. Next Steps Email: Educational content and self-service resources

4. Community Invitation: Invitation to join a relevant community/discussion group

5. Future Webinar Invite: Invitation to register for your next related upcoming webinar

6. Feedback Request: A simple survey to gather feedback and improve your content

7. Best-of Highlights: Key moments and takeaways from the webinar
   

Playbook #3: Build A Webinar Performance Dashboard in HubSpot

For B2B companies running webinars, there are two critical questions to answer:

1. Are our webinars driving meaningful engagement?

2. Are they ultimately contributing to revenue?

Using data integrated with HubSpot via Contrast we can build reports that connect 3 levels of webinar reporting (Activity, Pipeline, Program) to provide a complete view of webinar performance in HubSpot.

Step 1: Create a new dashboard:

Before diving into specific reports, create a dedicated dashboard to track your webinar program performance.

1. Navigate to: Reports > Dashboards > Create Dashboard

2. Name: Webinar Performance Dashboard

Step 2: Build webinar performance reports in HubSpot

Report #1: Became Lead

📀 Data Sources of “Contacts” 🎯
Group by “Date Entered Lead (Lifecycle Stage Pipeline)”
→ Values: Count of Contacts
→ Filter: Contacts - “Date Entered Lead (Lifecycle Stage Pipeline)” is known
→ Filter: Contacts - “Contrast last registration date” is “is known”

Report #2: Became MQL

📀 Data Sources of “Contacts”
🎯 Group by “Date Entered Marketing Qualified Lead (Lifecycle Stage Pipeline)”
→ Values: Count of Contacts
→ Filter: Contacts - “Date Entered Marketing Qualified Lead (Lifecycle Stage Pipeline)” is known
→ Filter: Contacts - “Contrast last registration date” is “is known”

Report #3: Became SQL

📀 Data Sources of “Contacts”
🎯 Group by “Date Entered Sales Qualified Lead (Lifecycle Stage Pipeline)”
→ Values: Count of Contacts
→ Filter: Contacts - “Date Entered Sales Qualified Lead (Lifecycle Stage Pipeline)” is known
→ Filter: Contacts - “Contrast last registration date” is “is known”

Report #4: Became Opportunity

📀 Data Sources of “Contacts”
🎯 Group by “Date Entered Opportunity (Lifecycle Stage Pipeline)”
→ Values: Count of Contacts
→ Filter: Contacts - “Date Entered Opportunity (Lifecycle Stage Pipeline)” is known
→ Filter: Contacts - “Contrast last registration date” is “is known”

Report #5: Became Customer

📀 Data Sources of “Contacts”
🎯 Group by “Date Entered Customer (Lifecycle Stage Pipeline)”
→ Values: Count of Contacts
→ Filter: Contacts - “Date Entered Customer (Lifecycle Stage Pipeline)” is known
→ Filter: Contacts - “Contrast last registration date” is “is known”

Report #6: Webinar-Influenced Pipeline

📀 Data Sources of “Deals” and “Contacts”
📊 Use the “Vertical Bar” chart type
→ X-Axis: Deal Create Date
→ Y-Axis: Sum of Deal Amount
→ Filter: Contacts “Contrast last registration date” is known
→ Filter: Deal Stage is not Closed Lost

Report #7: Webinar-Influenced Revenue

📀 Data Sources of “Deals” and “Contacts”
📊 Use the “Vertical Bar” chart type
→ X-Axis: Deal Create Date
→ Y-Axis: Sum of Deal Amount
→ Filter: Contacts “Contrast last registration date” is known
→ Filter: Deal Stage is Closed Won

Report #8: Webinar Registration Performance

Pre-Work:

1. Create a custom event using the “Track Object” event type

2. Choose “Contact” and “Contrast Last Registration” “Is Known”

3. Add an “Event Name” of “Contrast Webinar Registration”

Create the report
📀 Data Sources:
→ Primary: Contacts
→ Secondary: Custom Events
📊 Use the “Vertical Bar” chart type:
→ X-Axis: Select the “Contrast Last Registration” event and then “Timestamp” Date (Month)
→ Rename to “Webinar Registrations”
→ Y-Axis: Count of Contacts
→ Break down by: Contrast Last Registration

Report #9: Registration Source Analysis

📀 Data Sources of “Contacts”
📊 Use the “Horizontal Bar” chart type:
→ Values: Count of Contacts
→ Break down by: Contrast original source
→ Filter: “Contrast original source” is known

Using a webinar tool that integrates deeply with the rest of your marketing stack and enriches your CRM data in HubSpot makes it much easier to prioritize the right prospects and build a connected customer experience.

If you enjoyed these playbooks for running webinars in HubSpot I’d definitely recommend checking out the new HubSpot webinar academy I’ve been working on with the Contrast team.

It’s a tactical guide to scaling a webinar program on HubSpot and includes everything from promotion to reporting.

As you’re digging into the playbooks if you want to take a more in depth look at how Contrast works and how it integrates with HubSpot you can start a free trial or grab some time to chat with the Contrast team.

🕖 Subscribe to get new step-by-step playbooks for implementing a connected GTM motion in HubSpot every Thursday at 7:50am ET / 6:50am CT / 4:50AM PT.

Become a paid subscriber to receive additional newsletters each month, every playbook in the archive, and attend monthly office hours 🆕.

As the year comes to an end I want to say a big thank you to everyone who has read, subscribed, implemented, contributed or in any way supported ConnectedGTM.

Over the last six months of this newsletter, I’ve shared dozens of specific workflows, dashboards, and automation solutions for HubSpot.

Today, I want to highlight my 5 favorite playbooks of 2024 – all things you can build in your own HubSpot portal in an hour or two.

In the new year there will be new step-by-step playbooks along with more walkthrough videos, playbooks you can deploy in 1-click, and a ConnectedGTM first…

…a deeply researched guide to CPQ in HubSpot featuring multiple solutions partner perspectives and app partner integrations to compare.

If you’ve enjoyed the newsletter or have some raw feedback for what you’d like to see change for next year drop me a “reply”, I’d love to hear what you think!

Here’s to more playbooks, more connected GTM experiences, and growth in 2025.

See you next year,

– Stuart

p.s. I’ve added links to the complete step-by-step walkthrough for each playbook down below 👇

Playbook #1: Analyze Closed-Lost Deals

Closed lost deals are a huge opportunity most teams are missing 😩

When a deal is lost do you:
1. Consistently note the reason in your CRM?
2. Identify which stage the deal was lost from?
3. Retro the deal journey to identify how to improve the experience for future deals?
4. Engage lost deal contacts with a relevant nurture sequence?

This playbook covers how to improve your visibility into how and where deals are lost.

👉 Get the step-by-step playbook 👈

What’s included in the playbook:

1. Required properties for closed lost deals

2. Automated workflow to create a “Last Stage Before Lost” property

3. 4 custom reports for closed lost deals

   → Deals by Closed Lost Reason
   → Monthly Closed Lost Deals by Reason
   → Lost Deals By Last Stage
   → Monthly Lost Deals By Last Stage

Playbook #2: Build A Zero Duplicates Dashboard

Identifying and resolving duplicates accurately and consistently in HubSpot is a prerequisite to any effective strategy that leverages CRM data.

This dashboard will provide visibility into the number of duplicate records, sources of duplicates and causes of duplicates in HubSpot that can then be fixed either manually or automatically using a native HubSpot app like Koalify.

👉 Get the step-by-step playbook 👈

What’s included in the playbook:

1. A dashboard called “Zero Duplicates”
   

2. 12 reports to surface duplicate contacts and companies as they occur:
   → Count of duplicate contacts
   → Count of duplicate companies
   → Text content - why do we care about duplicates 👀
   → Duplicate contacts by source
   → Duplicate companies by source
   → Duplicate companies by create date (monthly)
   → Duplicate contacts by create date (monthly)
   → Duplicate companies by owner
   → Duplicate contacts by owner
   → Contacts by deduplication rule
   → Companies by deduplication rule
   → Contacts by deduplication property
   → Companies by deduplication property
   

3. 2 views to identify duplicate records
   → Koalify Duplicate Companies
   → Koalify Duplicate Contacts
   

4. 2 workflow actions for automatically merging duplicates

Playbook #3: Identify Expansion Opportunities With Product Usage Data

Increasing revenue (and all important revenue retention metrics) in a usage-based pricing model requires a deep understanding of how your users interact with your product.

Using product usage data, we can identify high-value customers, personalize outreach, and strategically target users who are most likely to upgrade.

👉 Get the step-by-step playbook 👈

What’s included in the playbook:

1. Custom properties for integrating product data using tools like June or Hightouch

2. Calculated properties for product utilization

3. Email template for automated usage snapshots

4. Automated workflow for proactive upsell outreach

Playbook #4: Define Multi-Level Approval Workflows

Create sophisticated approval workflows based on quote characteristics like discount level, deal size, or product mix. This playbook ensures proper oversight while maintaining efficient quote processing through automated approval chains and notifications.

👉 Get the step-by-step playbook 👈

What’s included in the playbook:

1. Quote rule implementation in quote•hapily

2. Automated approval actions in a HubSpot workflow

Playbook #5: Build A Pipeline Health Dashboard

Ensuring a clean and accurate pipeline requires discipline.

You could click into and review every deal record to understand recent activity (or lack of it). But who has time for that?

👉 Get the step-by-step playbook 👈

What’s included in the playbook:

1. Required fields to define stage entry/exit criteria
   

2. Dashboard to identify deals with missing data
   → Report #1 - Deals Missing Next Steps
   → Report #2 - Deals Missing Amounts
   → Report #3 - Deals Missing Next Steps
   → Report #4: Deals getting pushed
   → Report #5: Stalled Deals
   → Report #6: Stalled Deals by Stage
   → Report #7 - Deals Missing Data by Rep
   

3. Deal tags to visually highlight deals with data issues

🕖 Subscribe to get new step-by-step playbooks for implementing a connected GTM motion in HubSpot every Thursday at 7:50am ET / 6:50am CT / 4:50AM PT.

What happens after a sales call is critical to closing deals and accelerating revenue.

If the demo went well, chances are your prospect is excited, next steps are clear, and the deal feels close. Then reality sets in...

B2B buyers spend only 5-6% of their total buying journey meeting with any one sales rep, and just 17% meeting with all potential suppliers combined

This means for every hour your sales team spends with a prospect, there are nearly 5 hours where buyers are trying to navigate your solution, share information with colleagues, and build their business case - all without you in the room.

Yet most sales teams are still relying on disconnected emails and documents to manage complex, multi-stakeholder deals.

When critical information gets lost in endless email chains, buyers get confused, stakeholders drop off, and deals stall.

Today, we're covering how you can create engaging, self-serve buying experiences that guide prospects through their evaluation process - even when you're not there.

Highlights

→ Unite all your deal materials, conversations and stakeholders in one collaborative workspace that syncs with HubSpot

→ Automatically create personalized deal rooms with your prospect's branding directly from HubSpot deals

→ Track engagement from every stakeholder and sync all activity back to the HubSpot activity timeline

→ Build automated playbooks to guide buyers through your sales process and keep deals moving forward

As usual the exact steps to implement the playbook in HubSpot can be found at the bottom of the post. Let’s get into it.

Having all your deal-related content and stakeholder interactions organized in one place makes it much easier to keep deals moving forward and ensure everyone has the latest information.

There's nothing worse than having a prospect ask for materials you've already sent three times, or discovering a key stakeholder has been working with outdated information when they champion your solution internally.

While HubSpot's native documents and quotes features provide basic deal collaboration, managing complex multi-stakeholder deals often leaves teams struggling with scattered email threads and lost attachments. That's where Flowla can help.

Flowla features

Enhances HubSpot's native deal management capabilities with a dedicated space for buyer collaboration.

Create Deal Rooms Directly from HubSpot

Every deal in your pipeline can have its own dedicated workspace for collaboration created from the HubSpot deal record. Flowla automatically personalizes each deal room with your prospect's branding and pulls in relevant deal information from HubSpot using dynamic variables.

Centralize & Activate Your Sales Content

Avoid reps hunting through shared drives or wondering if prospects are working with outdated materials. Flowla centralizes scattered sales materials into an organized, dynamic content hub that's always up to date.

With native integrations to essential tools like HubSpot, Salesforce, Gong, and Clay you can create seamless buying experiences that keep everyone aligned. When you update content in your library, it automatically updates across all active deal rooms.

→ Organize content by sales stage, persona, or use case
→ Track performance of individual assets across all deals
→ Ensure stakeholders always see the latest versions
→ Embed dynamic content like calendars and forms

Track Stakeholder Engagement

See exactly who's engaging with your deal materials, even hidden decision makers who weren't originally on your contact list. All stakeholder activity automatically syncs back to HubSpot, creating new contact records and logging engagement data to help you spot buying signals and potential champions.

Revenue Intelligence & Real-Time Insights

Go beyond basic engagement tracking with detailed analytics that show exactly how prospects interact with your content. See which materials drive action, how much time stakeholders spend on each step, and get notified in real-time via Slack or email when there's activity.

For sales leaders, this means:

• More accurate forecasting based on actual buyer engagement, not just rep opinion

• Clear visibility into which deals to prioritize based on stakeholder activity

• Data-driven insights into which sales materials are most effective

• Real-time notifications when prospects share content with new stakeholders
  

💰 While the free tier includes basic flow analytics, Flowla’s Team and Enterprise plans unlock advanced content analytics, weekly AI pipeline summaries, and custom reporting dashboards to help you continuously optimize your sales process.

Step-by-step playbooks build a personalized buying experience for every deal in HubSpot

Building engaging buyer experiences takes more than just following up. You need a way to ensure the right information reaches the right stakeholders at the right time - and know when to proactively step in to keep deals moving.

Most sales teams try to solve this with a combination of shared drives, email tracking, and manually logging activities in HubSpot. But crucial signals often get missed:

→ The technical buyer who received a forwarded email with your security documentation

→ The CFO who spent 30 minutes reviewing pricing at 11pm

→ The new stakeholder who just joined the buying committee and needs to get up to speed

These invisible parts of the buyer journey often determine whether deals move forward or stall out. With Flowla integrated into your HubSpot instance, you can turn these blind spots into opportunities for engagement.

Let's look at two step-by-step playbooks for using Flowla to accelerate deals and improve buyer engagement right from HubSpot:

Playbook #1: Automatically create personalized deal rooms for qualified opportunities in HubSpot

When prospects are qualified and moved to a specific deal stage, automatically create and send them a personalized deal room to collaborate.

Here's how it works:

Step 1: Create a new flow template in Flowla

💡 Before building automation, create a flow template that will be your starting point:

1. Navigate to Templates in your Flowla account

2. Create a new template called "Post-Demo Deal Room"

3. Add standard sections for:

   • Meeting recap

   • Product overview

   • Technical documentation

   • Pricing & packages

   • Next steps timeline

   • Key stakeholder tasks

Step 2: Build the automated workflow in Flowla

⚡️ From the autopilot tab in Flowla select the “When deal status changes to something, create a flow from a template” workflow.

✅ Select the deal stage and flow template you would like to use for your automation.

Step 3: Create a follow up template with the deal room link

📧 Using HubSpot's email template builder:

1. Create new template "Deal Room Introduction"

2. Subject: "Everything you need to evaluate [company name]"

3. Include dynamic content:

Hi {{contact.firstname}}, 

I've created a dedicated workspace for your team to explore [Product Name] and collaborate with us during your evaluation: {{deal.flowla_deal_room_url}} 

You'll find: 
- A recap of our discussion 
- Product documentation 
- Technical specifications 
- Next steps and timeline 

Feel free to share this link with other stakeholders who should be involved. 

Best, 

{{sender.firstname}}

Playbook #2: Identify and engage hidden stakeholders

Use Flowla's stakeholder tracking to spot new decision makers and automatically create contact records in HubSpot. Here's how:

1. Create an active list of new stakeholders

   → Filters: Contact: Original Traffic Source Drill-Down 2 is "1044219" (this is the internal value for Flowla)

   → AND Created date is within last 7 days

   → AND Associated company has any deal

2. Create a deal tag for multi-stakeholder opportunities

   → Name: "👥 New Stakeholders Identified"

   → Color: Purple

   → Filters: Associated contact is member of "New Stakeholders" list

   → AND Deal stage is not Closed Won or Closed Lost

3. Build an automated workflow

   ⚡️ Trigger Criteria: Contact joins "New Stakeholders" list
   

   ✅ Action 1: Create task

   → Assign to deal owner

   → Task name: "New stakeholder {contact.firstname} viewed deal room"

   → Include flow engagement details in task notes

   🔔 Action 2: Send Slack notification
   → Channel: #sales
   → Message: "🎯 New stakeholder identified at {company.name}"
   → Include: Job title, engagement time, content viewed

The right buying experience can be a major competitive advantage - especially when 83% of B2B buyers say the experience is just as important as the product itself. By creating guided journeys inside Flowla that sync with HubSpot, you can give buyers the self-serve access they need to champion your solution internally while maintaining visibility into who is engaging.

As always, it’s important to test new products with your own workflows and data. Get started with a free Flowla account or book a demo for a personal walkthrough from the team.

🕖 Subscribe to get new step-by-step playbooks for implementing a connected GTM motion in HubSpot every Thursday at 7:50am ET / 6:50am CT / 4:50AM PT.

In HubSpot, quoting is often a “free-for-all".

The native quoting tools are powerful, and connect deeply to the deal management functionality revenue teams have built their workflows around. But…

Discounting and bundling compliance often falls to rep discretion or one-size fits all approval processes and teams resort to duplicating products to handle complex pricing scenarios.

As one sales leader put it:

"instead of seeing 100 units sold at different prices, you're seeing 30 units of product one, 37 of product two, 33 of product three" – it’s a reporting nightmare.”

The impact?

• inconsistent pricing

• wasted time on manual approvals

• messy reporting from duplicate products

• …and the constant risk of quoting errors.

So when Max Cohen showed me quote•hapily and was seriously fired up about how it made applying complex business logic to native HubSpot quoting super simple I was intrigued, and excited to be partnering on this week’s playbook.

Today, we’re covering how you can apply complex business and pricing rules to your quoting workflow inside HubSpot.

Highlights

→ Transform HubSpot's quoting tools into a sophisticated CPQ solution without leaving the CRM.

→ Automatically enforce pricing rules and approval workflows based on your business requirements.

→ Maintain clean reporting with unified product catalogs across teams and regions.

→ Control discounting and required product combinations with automated guardrails.

As usual the exact steps to implement the playbooks in HubSpot can be found at the bottom of the post.

If you’d like a look at more playbooks for complex CPQ use cases in HubSpot I also wrote this new guide and cheat sheet on the quote•hapily site.

Let’s get into it.

HubSpot's native quoting can feel like the "wild west" - reps can apply any discount and quote any product to any customer. While moving to a complex external CPQ system might seem like the answer, it often creates more problems than it solves.

quote•hapily enhances HubSpot's native quoting capabilities with sophisticated rules and workflows while maintaining the simplicity and deep integration to the tools your team already uses in HubSpot.

quote•hapily features

Smart Price Books

Create team or region-specific pricing without duplicating products. Maintain clean reporting while controlling which products teams can quote and at what price.

Quote Rules & Approvals

Set up automated guardrails to prevent unauthorized discounts and ensure quotes follow your business rules. Multi-level approval workflows route quotes to the right approvers based on specific triggers.

Dynamic Pricing

Automatically apply time-based discounts, promotional pricing, and customer-specific rates without manual calculations or separate spreadsheets.

Required Product Combinations

Ensure deals that meet specific quoting criteria include necessary services or add-ons by automatically enforcing product bundle requirements.

Automated Fee Calculation

Add shipping, handling, or support fees automatically based on quote conditions like deal value or product mix.

Tax Management

Apply the correct tax rates automatically based on customer location and product type, with support for multiple tax jurisdictions.

3 step-by-step playbooks for handling CPQ complexity in HubSpot

Let’s see how we can use our existing product library and deal configuration in HubSpot together with quote•hapily to apply our business and pricing logic to the quoting process in HubSpot:

Playbook #1: Create Price Books For Specific Teams or Regions

Provide reps with pricing and product access specific to their assigned team or region. This playbook prevents unauthorized quoting while maintaining accurate pricing across different markets and currencies, ensuring clean reporting and a streamlined rep workflow.

1. Create a team or region specific price book

   → Navigate to price books in quote•hapily

   → Create a new price book for each sales team

   → Add descriptive name (e.g., "NA Sales Team Products")

   → Add a description explaining usage
   

2. Associate your existing HubSpot products with price books

   → Select the products from HubSpot library

   → Add only products relevant to each specific team
   

3. Apply a currency based price override to price books for teams who don’t use your “standard” pricing in your company currency

   → Click “Override All Prices” → Currency: Specify the currency used by appropriate team for this price book → Enter Percentage Decrease: 0 (we are only changing the currency used)
   

4. Create a new quote rule → Name: Display { region } Price Book for { region } Sales Reps → Description: Automatically apply discounts for specific pricing tiers in Q4.
   

5. Add conditions to the quote rule

   → Any of the conditions below

   → “Team” IS “{Region} Sales Team”

   

   💡 Alternatively, use a company property to match the region using:

   → Any of the conditions below

   → “Company” > “Country/Region” > “Contains” > “United States”

   

6. Select quote rule outcome

   → Set price book (Choose the Price Book to apply to quotes that trigger this rule.)

   → Choose "Price Book Name" eg. “EU Product Catalog”
   

7. Verify your price books by creating a test quote

   • Create test quote using different companies

   • Confirm correct pricing and currencies are visible

   • Validate that incorrect products are hidden
     

Playbook #2: How to implement multi-level quote approvals in HubSpot

Create sophisticated approval workflows based on quote characteristics like discount level, deal size, or product mix. This playbook ensures proper oversight while maintaining efficient quote processing through automated approval chains and notifications.

The approval process in quote•hapily can automatically route quotes based on specific triggers like discount levels or deal size. The system has built in checks for tracking multiple pending approvals and only publishes quotes once all required approvers have signed off, ensuring proper oversight without creating unnecessary delays.

💡Start with your most common approval scenarios and gradually add complexity as your team adapts to the new process.

Here’s how it works:

1. Create a new quote rule in quote•hapily
   → Name: Guardrails: Require Approval
   

2. Add conditions to the quote rule
   → Any of the conditions below
   → “Line Items” > “Discount Percentage” > “Greater Than or Equal To” > “15”
   → “Line Items” > “Discount Percentage” > “Less Than or Equal To” > “25”
   

3. Select a rule outcome
   → Select: Require Approval
   → Message: Quotes with discounts between 15-25% require approval.
   → Checkbox: Check “Add to Approval Queue”
   → Approval Queue: “Sales Approvals”
   

4. Create an automated quote based workflow in HubSpot

   → Trigger the workflow when an event occurs

   → Has completed: Property value change

   → Property name is Quote approval status

   → New value: Quote approval status is any of Pending approval
   

5. Create a branch and check branches in order

   → Needs Sales Approval: quote•hapily Approval Queue is any of Sales Approval

   → Needs Finance Approval: quote•hapily Approval Queue is any of Finance Approval

   → No Approval Queue Set: If none of the criteria are met
   

6. Branch: Needs Sales Approval

   → Action 1: Use the quote•hapily “Request Quote Approval” workflow action to send the quote for approval to your desired sales approver email address.
   

   💡 The “Request Quote Approval” action checks all approvals have been accepted before releasing the quote to the next step in the workflow.
   

   → Action 2: Use the quote•hapily “Publish the Quote” action to publish the quote for prospects.
   

7. Branch: Needs Finance Approval

   → Action 1: Use the quote•hapily “Request Quote Approval” workflow action to send the quote for approval to your desired finance approver email address.

   → Action 2: Use the “Go To Action” workflow action to route the workflow to the quote•hapily “Publish the Quote” action in the first branch.
   

8. No Approval Queue Set

   → Action 1: Use the “Go To Action” workflow action to route the workflow to the quote•hapily “Publish the Quote” action in the first branch.

Playbook #3: How to create and enforce product bundle requirements

When selling complex products, ensuring the right combination of products, services, and support is crucial for customer success. Without automated enforcement, sales teams often forget critical components or struggle to maintain consistency in their quoting process.

By using rules to enforce product combinations, you can eliminate guesswork and ensure every quote includes all necessary components, while maintaining the flexibility to handle exceptions through the approval process.

→ Build your bundle requirements based on your most successful customer implementations to ensure new customers get the support they need to be successful.

Here’s how it works step-by-step:

1. Create a new “Notify” quote rule
   → Name: Guardrail: Require Implementation for Enterprise Plans
   → Conditions: “Any of the conditions below”
   

2. Add conditions to the quote rule
   → Any of the conditions below
   → “Line Items” > “Name” > “Contains” > “Enterprise”

3. Select a rule outcome
   → Outcome Type: “Notify”
   → Notify Message: “You must include implementation when selling an enterprise plan.”
   

4. Create a new “Block” quote rule

   → Name: Guardrail: Block Enterprise Quotes without Implementation
   → Conditions: “Any of the conditions below”
   

5. Add conditions to the quote rule
   → Any of the conditions below
   → “Line Items” > “Name” > “Contains” > “Enterprise” → “Line Items” > “Name” > “Is None Of” > “Implementation”
   

6. Select a rule outcome
   → Outcome: Notify
   → Notify Message: “Before you can publish a quote you must add implementation for enterprise plans”
   

7. Verify your quote rules by creating a test quote

   → Create test quote that includes an “Enterprise” line item

   → Confirm correct pricing and currencies are visible

   → Validate that the quote cannot be published

Making CPQ process changes fit your team’s existing workflow makes it easier to drive adoption and process compliance while also improving your revenue outcomes.

That’s a big vote for HubSpot native apps like quote•hapily vs integrating a disconnected 3rd party solution.

As always, it’s important to test new products with your own workflows and data. Start a free 14-day quote•hapily trial or book a demo for a personal walkthrough from the team.

🕖 Subscribe to get new step-by-step playbooks for implementing a connected GTM motion in HubSpot every Thursday at 7:50am ET / 6:50am CT / 4:50AM PT.

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Let me ask you this:

How confident are you in your process for closing new business?

How about this:

Are you more or less confident in your process for winning renewal deals?

Once a new contract is signed, it’s easy to get caught up in acquiring the next customer rather than nurturing the ones already on board. But that makes it easy for revenue churn to sneak up on you and you forecast 😬

Today, we’re covering how to build automated renewal management in HubSpot that not only works behind the scenes, ensuring nothing slips through the cracks, but is also proactive, to help identify at-risk customers and expansion opportunities.

Highlights

→ Define your renewal process in a dedicated HubSpot deal pipeline and trigger the right milestone or time-based playbook for each customer.

→ Automatically move deals through your renewal pipeline as they make progress towards their renewal date.

→ Discover 2 simple methods for creating subsequent renewal deals and transferring the required context to the next phase of the customer journey.

As usual, the exact steps to implement this playbook in HubSpot can be found at the bottom of the post. Let’s get into it.

This newsletter is part 1 of a 3-part series on managing recurring revenue in HubSpot

Here’s what we’ll cover:

Part 1 (this newsletter):

• How to build and automate your renewal pipeline

• A step-by-step renewal enablement playbook

Part 2:

• A deep dive into building strategic account plans and proactively enabling customer outcomes that drive renewals and expansion

Part 3:

• Revenue reporting

• Renewal and expansion revenue forecasting

Bonus for paid subscribers:

• Pre-built playbook that you can one-click deploy and implement this system in your own HubSpot account.

• Office hours with me on 11/14, part of a new monthly series for paid subscribers. If you have questions or want to hear me discuss this newsletter, become a paid subscriber, then RSVP here.

Customer renewals are the most critical element of a recurring revenue business model and yet the element we hope to make the most anti-climactic event of the year.

Ultimately running an effective renewal process is much like closing an initial deal, you need context about your buyers experience, goals, and constraints to take the right action. The renewal process in HubSpot looks something like this:

1. Close a new deal in your sales pipeline

2. Trigger a workflow to handoff from sales to onboarding/customers success/account management (create a renewal deal in the process)

3. Automatically move the renewal deal through the renewal pipeline

4. Check for falling health scores (at-risk) or expansion opportunities along the way

5. At a defined time to renewal (90 days) kickoff your renewal playbook

6. Send automated reminders for auto-billing

7. Close the renewal deal (renewed or churned)

8. If renewed create a subsequent renewal deal and repeat the process

Using a dedicated renewal pipeline and automatically creating deals for future renewals reduces manual work for your team AND provides an effective way to trigger engagement throughout the lifecycle to ensure renewals are a non-event.

However, if you have seen any of the previous content I created about automating renewal management in HubSpot you’ll know this workflow requires a pretty wild hack to get round a HubSpot limitation out of the box. That’s where CloneNer can help.

Features

Built to be a native extension of HubSpot, the CloneNer app provides a simple way to clone HubSpot objects either manually or automatically. Perfect for recurring processes such as renewal management.

Clone HubSpot objects directly from the CRM card in each record

The CloneNer CRM card is available in the right sidebar of each record and allows manual duplication of both properties and associations.

Automatically clone records using auto-rules

Once you have clear definition around when you want to duplicate records on a recurring basis and the information that you need to transfer to the newly created record auto-rules in CloneNer provide a powerful alternative to HubSpot workflows.

💡 HubSpot workflows are incredibly powerful but have limitations specifically for the record duplication use case when it comes to which records you can enroll and which attributes you can clone.

Update property values in cloned records

Each time you duplicate a record you will likely have some properties that need to stay the same and some that should be updated such as the renewal year or the name. If you are using auto-rules you can dynamically set new values using personalization tokens.

Maintain specific associations while duplicating records

Select associations you wish to preserve in the new record across available HubSpot objects.

How to build and automate your renewal pipeline in HubSpot (step-by-step)

Starting with a clearly defined process is a precursor to increasing internal adoption and reporting accuracy. Use these playbooks to start defining your renewal management process in HubSpot and lay the foundation for automation and

Here’s how to set up your renewal system step-by-step:

1. Track renewal dates on the company record

When a new deal is moved to closed won in our sales pipeline we need to make sure that the company record reflects the next renewal date for the account. We can achieve that with workflow action and a simple custom property.

1. Create a custom property on the company record for “Next Renewal Date”.

💡 HubSpot now has the option to show the date relative to today in date picker properties – perfect for showing renewal dates.

2. Automatically update the renewal date property in handoff workflows.

Building an automated process for sales handoffs when a new deal is closed won was the subject of the very first edition of ConnectedGTM.

2. Build a clear view of upcoming renewals

The first step to proactively managing renewals in HubSpot is to provide a list of accounts with upcoming renewals to your team. This can use our custom company property from step 1 that is:

→ Updated manually when a new deal closes.
→ Updated automatically via workflow when a new deal closes.
→ Synced via a billing integration like Stripe.
→ Synced from a product analytics tool like June.

Once you know which method you’ll use to identify renewal dates we can use that property to create lists of accounts using 3 different methods in HubSpot.

As well as providing clear visibility into which accounts have upcoming renewals, these lists can also highlight important information about these accounts product usage to the account owner.

Here’s an example of the columns you might choose to include in your upcoming renewal lists:

→ Company Name
→ Next Renewal Date
→ ARR
→ Health Status
→ Usage Trend (synced from your product)
→ Total Seats (synced from your product)
→ Active Seats (synced from your product)
→ Last Activity Date
→ Company Owner

Account List Method #1: HubSpot Active Lists

Create an active list of accounts (companies)

1. Add a filter: “Next Renewal Date” is less than “90 days” from now

2. Edit columns: Based on your property preferences
   

Account List Method #2: HubSpot Companies Saved View

1. Create your view:
   → From the Companies list page, click “Add View”
   → “Create new view”
   → Name your view: “Renewals Next 90 Days”

2. Add a filter:
   → Click “Advanced filters”
   → Filter: “Next Renewal Date” is less than “90 days” from now
   → Save View

3. Edit columns: Based on your property preferences

Account List Method #3: HubSpot Customer Success Workspace

If you have a HubSpot Service Hub subscription, you can also access all your renewal information inside the customer success workspace.

When you set up the customer success workspace you’ll be prompted to tell HubSpot which property will be used to represent your customers renewal date.

Once you have set the property that represents your customers renewal date, HubSpot will display a default view in the workspace “Portfolio” tab for accounts “Renewing in the next 90 days”.

💡 If you prefer to customize the columns displayed you can also create a private view. Note: private views are not displayed on the workspace summary tab.

Now we have visibility into which accounts have upcoming renewals, we can build a repeatable proactive renewal process to support them.

3. Build and automate a dedicated renewal pipeline in HubSpot

Using a separate pipeline for each stage of the customer journey, for example sales and onboarding is always recommended.

Intermingling stages of the customer lifecycle in the same pipeline make it more difficult to run effective reporting, more difficult to understand who owns the customer and process at any particular moment in time, ultimately making it much harder to run a repeatable process.

Organizing your renewal pipeline based on the time to renewal makes it possible to align your process to key milestones in the customer lifecycle. Start by breaking your renewal pipeline into quarterly stages

→ Automated Stages (we’ll do this below): 6-12 months, 3-6 months, 1-3 months
→ Manual Stages: 1 month, Renewed (closed), Churned (closed)

💡 Pro Tip: Automate movement through the pipeline using workflows based on close dates. This keeps everything on track without needing manual updates.

Create a workflow to automate pipeline progress

For this step we have a new way to track how many days there are until renewal with the “Time until” calculated property type.

This means we no longer need a separate Today’s date property or complicated and hacky way to keep it up to date.

2.Create a deal based workflow and trigger it when:
→ Property value changed → Property name is Days to Renewal
→ New value: Days to Renewal is known 
→ Pipeline: Renewal Pipeline

3. Branch the workflow based on “Days to Renewal” for each stage of the renewal pipeline.
→ 6-12 Months: Renewal Date > 182 days from now
→ 3-6 Months: Renewal Date > 90 days from now AND < 183 days from now
→ 1-3 Months: Renewal Date > 30 days from now AND < 91 days from now
→ 1 Month: Renewal Date < 31 days from now

4. For each branch of the workflow set the pipeline stage to match the branch.

4. Automatically create subsequent renewal deals

Try this simple alternative to building multiple complex workflows to create subsequent renewal deals in HubSpot using CloneNer.

Here’s how it works:

1. Create a dedicated renewal pipeline using HubSpot deals

2. IF automating renewal deal creation:
→ Create a calculated property for “Next Renewal Year”
→ year([properties.renewal_date]) + 1

3. Create the first renewal deal for each company when a new sales deal closes using the name format: {company name} - Renewal { year }

Option 1: Manual 🙋:

4. When you open the record page for a newly closed renewal deal, find the CloneNer CRM card in the right sidebar and click “Duplicate Deal”.

→ Why? Because we want to transfer all the context, property values, and associations for contacts, companies, and line items to our deal record for the next renewal period without hacky workflows.

5. From the CloneNer window, update critical details
→ Deal Name: {company name} - Renewal {next renewal year}
→ Deal Amount: Copied from the current deal
→ Renewal Year: Update to the next year
→ Modify any additional properties needed for your business

Option 2: Automated 🤖
4. From either the CloneNer CRM card on a deal or the settings page click actions and then “Auto Rules”

💡 Auto Rules are mini workflows specifically for duplicating HubSpot records.

5. Create a new auto rule called “Create Subsequent Renewal Deals”
→ IF a deal from the “Renewal Pipeline” enters Deal Stage “Renewed”
→ THEN create a new deal in the “Renewal Pipeline” placing it in the 6-12 months stage.

6. Update your critical deal details, instead of changing values manually we can use {{ }} syntax to include dynamic property values. eg.
→ Deal Name: {{ company name }} - Renewal {{ next renewal year }}

7. Select your deal associations to also be duplicated to the new deal. At a minimum, I would suggest Contacts, Companies, and Line Items.

5. Automate Renewal Reminders and Tasks

As with any process in the customer lifecycle, once we have our data and process defined inside HubSpot we can layer in automation to save our team time and provide a consistent experience at scale for customers.

1. Create a company based workflow

⚡️ Trigger Criteria:
→ List membership changed
→ is added to list Upcoming Renewals (Next 90 Days)

2. 🔔 Send a Slack notification
→ Send to existing company owners
→ Message: “Renewal for. { Company Name } is coming up 90 days from now on { Next Renewal Date }
→ Properties to include: Health Status, CSM Sentiment, Plan, ARR, Usage Trend, Active Seats

3.📧 Send an automated email to the customer
→ Send to all contacts with the “Billing Contact” association label
→ Use an Upcoming Renewal Notification template that includes details of when and how the customer will be billed.

4.✅ Create an internal task → Name: Review account data for upcoming renewal → Assigned to: Company owner

This workflow is just a starting point and we’ll cover more in depth renewal playbooks and automation in the next edition in the series.

6. Customize the company record layout for renewals

Removing friction from how teams discover and interact with renewal data in HubSpot can make a big difference to their ability to support customers effectively.

We can use HubSpot’s record customization features to present data that is the most relevant for the renewal phase of the customer lifecycle.

We’ll customize 3 configurable areas of each company record:

1. Deal record - Center panel customization

Click “Customize Record” in the top right of the center panel for any company record. Then select to edit either the default view or create a new team specific view if you want to show each team a different layout.

1. Recommended Enablement - This is a default HubSpot UI card that can be added by selecting the “Recommended Enablement” card and then dragging it to the top.

2. Active Deals - This card will display deals across pipelines that are currently open, existing customers will likely have a renewal deal and potentially upsell or expansion deals to consider.
   → Click “Add Card” and then select “Association Table”
   → Card Title: Active Deals
   → Properties: Deal Name, Amount, Close Date, Deal Type
   → Filter: Is Open is equal to “1”

3. Upcoming Activities - This is a default HubSpot UI card that will display all activities such as tasks and meetings with a date in the future.

2. Deal record - Left sidebar customization

Section 1: Account Overview
→ Company Owner, CSM Sentiment, CSM Sentiment Details, Plan, ARR, Next Renewal Date

Section 2: Product Usage Data
→ Total Seats, Active Seats, Usage Trend, Feature #1 Usage Total, Feature #2 Usage Total, Feature #3 Usage Total

3. Deal record - Right sidebar customization

→ Health score, Contacts, Deals, Tickets, App CRM Cards (CloneNer)

Taking a process driven approach not only increases renewal rates but also strengthens your relationship with customers by ensuring you can remain proactive and focused on their needs instead of manually managing process.

As always, it’s important to test new products with your own workflows and data, so don’t hesitate to try CloneNer in the HubSpot marketplace, or get in touch with the CloneNer team if you have any additional questions. 

🕖 Subscribe to get new step-by-step playbooks for implementing a connected GTM motion in HubSpot every Thursday at 7:50am ET / 6:50am CT / 4:50AM PT.

There’s no question that signal-based selling is hot right now.

But while many sales teams have tried using signals, they often run into frustrating issues that cause friction and ultimately waste time as they try to scale…

1. Inaccurate signal data

2. Delayed signal information

3. Lack of integration with existing systems

These problems result in a lack of activation by reps, who end up ignoring the signals altogether. The classic "garbage in, garbage out." scenario.

Yet, despite all the new buzz around signals, the best sales reps have been successfully leveraging signals for years.

Job change signals, for example, are one of the clearest, most easily triggered, and widely available signals for sales opportunities, often resulting in a 10-50% increase in pipeline generated.

New executives spend 70% of their budget in the first 3 months

Today, we’re digging into how you can use job change (and related) signals to fill your sales pipeline in HubSpot without adding operational complexity, enabled by LoneScale.

Highlights

→ Monitor your current customers and past opportunities for job changes and upcoming projects to turn their company changes into new opportunities.

→ Identify target accounts using the tools you're partnering with, integrating into, or competing against, and identify expansion opportunities as former customers join open opportunities.

→ Capture job changes at scale as tasks or custom objects in HubSpot and automatically enroll contacts in relevant sequences and ad audience lists.

As always, the exact steps to implement this playbook in HubSpot can be found at the bottom of the post. Let’s get into it.

Become a paid subscriber to receive 2 extra newsletters each month, the how-to steps for every playbook in the archive, and attend monthly office hours 🆕

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Accurate job change signals are so valuable as a trigger for sales outreach because:

1. Past buyers are 5x more likely to convert into closed-won revenue than cold leads

2. 89% of previous customers don't come back on their own when they start a new role

So why do new hires convert to pipeline at a higher-than-normal rate?

• New hires (especially executives) are looking to make an impact quickly and leveraging familiar tools will likely be part of their initial plan.

• Capturing job changes of existing customers enables reps to leverage their existing relationships in a new context instead of starting cold.

• Job changes often signal company growth or new initiatives which translate to budget and willingness to spend to accelerate outcomes.
  

Yet most sales teams are leaving money on the table by not consistently tracking and acting on these triggers.

🕰️ Old way of tracking job changes:

• Manually checking LinkedIn for job changes

• Inconsistent data entry in the CRM

• No systematic follow-up process

• Limited visibility into pipeline impact

🚀 New way:

• Automated job change tracking

• Real-time CRM integration

• Prioritized outreach based on ICP fit

• Clear reporting on pipeline generated from job change signals

The key to success is simplification not added complexity. Creating an efficient sales engagement workflow is especially important as sales teams shift towards a full-cycle model where reps are responsible for both prospecting and closing. They need:

• Easy access to all the necessary data in their daily workflow

• Automated task creation for high-priority job change follow-ups

• Clear playbooks for different job change scenarios

If you don’t want reps stuck manually monitoring LinkedIn or navigating your CRM each time a contact at a target account switches roles, LoneScale can help.

Features

LoneScale is available in the HubSpot app marketplace and provides high-intent signals to help generate pipeline without needing reps to adopt and train on yet another platform.

Accurately track Job Changes of your existing contacts

Track changes at your key clients, closed-lost accounts, and open opportunities to identify potential opportunities to align your offer with the changing needs of the business. LoneScale tracks job changes at accounts specified in HubSpot lists ensuring you are paying attention to the accounts that matter to you.

💡 LoneScale double-checks the LinkedIn URL to reduce false positives, making sure the contact’s details match across domains and job history.

Track new hires at target accounts

Unlike job changes, where you already have a relationship with the contact. Tracking new hires targets existing accounts where someone new has recently joined (often decision-makers specifically).

💡 LoneScale recommends tracking executives within their first 100 days, as they’re more likely to evaluate new tools and make changes.

Identify upcoming projects

New job postings can often contain indications of upcoming projects that your target accounts are ready to invest in. These postings can make it possible to find potential leads using the tool you're partnering with, integrating into, or competing against.

💡 LoneScale extracts relevant information from job postings beyond just their existence as a signal, such as the company mission and potential tools being used to help reps craft the most relevant outreach messages and reduce the number of additional research steps.

Enrich HubSpot records with signal data

Ensuring HubSpot records always include accurate contact information for sales outreach is critical to save reps time and ensure new signals are activated quickly.

LoneScale provides native integrations with providers like Apollo and ZoomInfo to enable automated enrichment of contact information. These enrichment workflows can also be run on a schedule ensuring stale info is regularly refreshed.

Create custom objects (or tasks) in HubSpot for new signals

The best case when implementing new tech is to make your reps' lives easier, not add another tool to their already overflowing stack. LoneScale offers flexibility and a lot of customization for how to integrate signal data with HubSpot.

Option 1: Custom Objects: Ideal for reporting on signals over time, custom objects allow you to track job changes and new hires as unique records. You can associate these changes to both contact and company records for deeper insights.

⚡️ Intent custom objects can be customized and created automatically in HubSpot from your LoneScale settings.

Option 2: Tasks: If you prefer a simpler setup (or don’t have a HubSpot enterprise subscription), tasks can be automatically created to notify your team of changes and include relevant context to inform the next step.

How to take action on job change signals in HubSpot to build your pipeline (step-by-step)

LoneScale’s HubSpot integration enables reps to engage prospects with new job change signals directly. Here’s how it works step-by-step:

Step 1. Create a Job Change Workflow in LoneScale

LoneScale is designed to automatically track job changes and new hires within your specified accounts.

1. In LoneScale, navigate to the Track Job Changes button in the top right. In the Input section search and import your HubSpot contact lists (either active or static) to start tracking job changes.

2. Optional* Enable LoneScale’s data enrichment to pull additional details

   → Select your desired data providers (e.g. ZoomInfo, Apollo, or Waterfall.io)

   → Set your preferences for data enrichment (e.g. enrich only if empty, replace, or add new information).
   

3. Optional* Enable LoneScale’s contact sourcing feature

   → Define the personas you want to target (e.g. C-suite, department heads)

   → Choose sourcing criteria (e.g. company size, location, or industry)

   → Configure enrichment for sourced contacts to retrieve their email and phone numbers before importing them into HubSpot.
   

💡 Make sure your tracking includes both inbound (new hires at target accounts) and outbound (contacts moving to new companies) job changes.

💡To get started consider uploading a CSV with a small number of accounts to see what data is captured and identify any tweaks needed before fully automating your process. Once you’re confident in the data accuracy, switch to an automated flow where LoneScale integrates directly with HubSpot. The data can be updated regularly (e.g., every 30 days) to ensure you’re always working with the latest information.

Step 2. Connect intent data to HubSpot

The ROI of using a tool to identify buying signals at scale like LoneScale ultimately happens when job change data flows automatically into HubSpot enabling you to:

→ Automatically update contact records
→ Trigger tasks for sales reps
→ Include job change info in account views

So what options do you have when LoneScale identifies a new signal?

Option 1: Create HubSpot tasks

The simplest way to start notifying your reps of new signals at your designated accounts is to create tasks using LoneScale’s pre-built template.

You can customize the tasks by selecting:

→ the task assignee
→ the priority of the task
→ the title of the task
→ the content of the task (Contact data, Company data, Job postings data, Your category & highlighted context)

Here’s an example of the LoneScale template for new hiring signal tasks:

💡Consider creating a job change signal task queue in HubSpot for sales reps so they can prioritize their outreach to new hires or job changes efficiently.

🚨 The downside of using tasks to track new intent signals in HubSpot is they are difficult to report on and gather insights about over time to determine what’s working well and what is not.

Option 2: Create a custom object in HubSpot

Creating a custom object to track newly identified intent signals in HubSpot provides the most flexibility for how different scenarios are operationalized and reported on.

It’s critical to consider how your intent data will be activated in your reps’ workflow and design your custom object accordingly.

💡 LoneScale checks if contacts already exist in HubSpot and updates them instead of creating new records, unless specified otherwise to avoid duplicate records.

💡 You can maintain multiple email addresses for a contact in HubSpot, with the ability to designate which one is primary.

Here’s how to create your new custom object for Intent:

1. Create a Custom Object in HubSpot called “Intent”.
   

2. Add an “Intent Type” property

   → Radio Select field with options for Job Postings and Job Movements

   → Optional* add additional options for Website Visits, Comparison Search, Content, Community, Competitor, Event, Social Selling, and Fundraising.
   

3. Define the available associations for the Intent object

   → Add an available association to company records

   → Add an available association to contact records
   

4. For each Intent Type add relevant property groups
   

   → Job Signals (Hiring): Category, Stack, Department, Level, Id, Job board name, Keywords, Context
   

   → Job movements (Job Changes + New Hires): Changed company, Changed job, Promotion, Is New Hire, Job title, Department job title, Level job title, Old job title, Old Company, Tenure company length, Tenure position length, Start company date, Start position date
   

5. Customize your record view to display job change intent data in the left sidebar.

   → Update the “About this Intent” card to only show the date, intent type, and country.

   → Add an additional section called “Job Movements” which is only displayed when the intent type is Job Movement.

   → Add the custom Job Movement properties to this record customization card.

Step 3. Trigger proactive engagement playbooks

Not all job change signals are created equally. It’s a good idea to have an account prioritization system based on factors like:

• ICP fit of the new company
• Seniority of the new role
• Previous relationship with the contact
• Relevance of your solution to likely priorities in the new role

🔥 Bonus: Don't forget job changes at your existing customers can be great expansion opportunities. Make sure your customer success team is looped in to these triggers.

We can use automated scoring and workflow enrollment to ensure your team focuses on the highest-value opportunities first. Here’s how it works:

1. Create an intent-based workflow
⚡️ Trigger Criteria: Object Creation

🌴 Branch: Based on Filter Criteria
→ If “Intent Type” is “Job Movements” go to the Job Movements Branch
→ Optional* Add additional branches for other intent types you are tracking

IF Intent Type is any of “Job Movements”

🤖 Set property value
→ Primary company property “Intent” to “Job Movements”

🔔 Send a Slack notification
→ Notify: the #sales channel
→ Message: 🚨 New {{ enrolled_object.intent_name }} identified

✅ Create a task to enroll the contact in a sequence
→ Add this task to the “Job Changes” task queue

Repeat these branched steps for each intent type you would like to automate your playbook and reporting for.

2. Send personalized outreach communications

The key to success with job signals is to pair 1) the reason for reaching out (signal, or stack of signals) with 2) the right message in a well-crafted, multi-touch outreach strategy.

📧 By combining an existing relationship with a new signal (job change in this example) we can send a highly relevant message at the right time.

Looks like you've moved on from {intent.previous_company}, {contact.first_name}. 

Congrats on the new gig! I'm sure you're just getting your feet under you at {new_company}, but do you think it makes sense to link back up in a month or two once you've got an understanding of how {process} works at {new_company}?

🤝 If we have not previously connected, or if this is a new account added to our list we could also send a LinkedIn connection request and follow up a couple of days later with a relevant message.

🎯 Depending on the size and value of a new account, you could also add them to an audience for targeted ads. Whenever possible match the creative and message of the ads with the new priorities and context of the new role.

💡 Pro Tip: Create templates and sequences specifically for job change scenarios.

Step 5. Build an intent signals dashboard

What gets measured, gets managed. Set up dashboards to understand the influence of job change signals rep’s outreach and deal outcomes.

Report #1 - Response rates to job change-triggered outreach

📀 Primary data source of "Sequences"
💿 Secondary data source of “Intents”
📊 Use the Vertical Bar chart type:
→ X-Axis: Timestamp - Monthly
→ Y-Axis: Count of replies from sequence
→ Breakdown by: Intent Type
→ Filter: Intent Type is any of Job Movements or Job Postings

Report #2 - Pipeline generated from job change opportunities

📀 Data sources of "Deals"
💿 Secondary data source of “Companies”
📊 Use the Vertical Bar chart type:
→ X-Axis: Create Date - Monthly
→ Y-Axis: Sum (Amount)
→ Breakdown by: Intents
→ Filter: Pipeline is any of Sales Pipeline
→ Filter: Intents is any of Job Movements or Job Postings

Report #3 - Closed-won deals originating from job change alerts

📀 Data sources of "Deals"
💿 Secondary data source of “Companies”
📊 Use the Vertical Bar chart type:
→ X-Axis: Close Date - Monthly
→ Y-Axis: Sum (Amount)
→ Breakdown by: Intents
→ Filter: Deal stage is any of Closed Won (Sales Pipeline)
→ Filter: Intents is any of Job Movements or Job Postings

Regularly review these metrics and refine your approach based on what's working best. Remember, consistently following a simple process is key. Make job change outreach a core part of your sales motion, and you'll see the pipeline grow!

Job change signals are a powerful, yet often underutilized tool for sales teams. Focus on integrating high-quality signals and implementing them in a way that doesn't disrupt your rep’s existing processes.

As always, it’s important to test new products with your own workflows and data, so get in touch with the LoneScale team if you have questions or want to try the product for yourself and see how job change signals can be leveraged to drive pipeline.

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