How to Turn HubSpot into a Retention Engine (Customer Success Workspace)

Connect the custom journey in one place to proactively identify churn risks.

👋 Hey, I'm Stuart, and welcome to ConnectedGTM. This edition has been made available for 💸 FREE 💸 by Infinite Renewals | Turn HubSpot into a scalable retention engine in with operator-led playbooks for customer success.

---

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.

---