How to hit your retention goals in 2025 - like a boss

Retention isn't just about stopping users from clicking the dreaded "cancel" button—it's about understanding why they're considering it in the first place. 

And - fun fact - they may have "emotionally churned"  from your product long before they hit the "Cancel" button / their contract expires. According to Ibrahim Bashir:

"Emotional churn describes the phenomenon where end-users mentally disengage from your product, independent of any contractual arrangements. This disengagement often occurs long before the actual buyer, the person who authorized the purchase, terminates the contract.

At its core, emotional churn occurs when your target users become psychologically ready to explore alternatives, though they haven’t yet taken concrete steps to evaluate competitors. This creates a dangerous period where your deployment exists in a state of apathetic limbo, hampering expansion opportunities.

The most telling indicator of emotional churn is the disappearance of product champions within an organization. When emotional churn takes hold, you’ll notice fewer advocates and active users."

Can you spot the signs of Emotional Churn?

It happens for a number of reasons: 

• Poor onboarding and a long learning curve.

• Inability to complete the main workflow, especially in comparison to other solutions.

• Integration challenges with other tools in their workflow.

• A lack of multiplayer mode and collaboration features that allow a collaborative environment.

How to spot it before it happens? 

First, it’s important to understand and monitor the core flows of your product: are they being exercised with the same frequency and level of engagement as always?

Looking at feature-level adoption is a great way to understand if users are engaging in behaviors that make them stick. If new features are built and launched with customer learning rigor but don’t get utilized, that is a sign of emotional churn setting in. 

Here's what else you can do to quickly spot it: 

1. Use analytics to identify accounts with declining usage and flag them for intervention. Your customer success team should have a playbook for re-engaging these accounts before it’s too late. 

2. Identify power users or champions within the account and empower them to advocate for your product internally. Give them exclusive access to new features, invite them to beta programs, or spotlight their success stories. 

3. If users are frustrated, show them you’re listening. Share how their feedback has influenced your roadmap, and prioritize fixes or improvements that address their pain points. 

Read more about Emotional Churn here

But spotting it is half the battle. The other half is understanding WHY it happens. 

Enter Retention Research. 

According to Nikki Andersson, a user research consultant: "Retention research dramatically impacts organizations by revealing why customers stay or leave, influencing revenue, lifetime value, and acquisition costs.

The key advantage of user research is its focus on outcomes beyond metrics. Approaching projects solely with goals like “increase retention to 70%” emphasizes business outcomes while neglecting user outcomes. Users won’t stay simply because we want to retain them.

Users stay with products because of the positive experience the product creates for them. This positive influence can come in the form of:

• Helping them achieve a goal.

• Making a task more efficient.

• Alleviating a recurring pain point.

• Making their day-to-day life easier.

• Enabling them to do a difficult task more effectively.

• Meeting an unmet need that they can’t get met elsewhere.

A product serves a purpose for people. By clearly understanding the purpose, goals, needs, and pain points, we can start to understand how we might help people and encourage them to stay. User research is the key to developing that understanding."

Here are the steps to conduct retention research, simplified into bullet points:

• Define retention clearly: Identify specific behaviors, frequency, and timeframes that characterize a retained user at your organization.

• Clarify business goals and metrics: Set measurable objectives for what successful retention looks like for your project.

• Identify gaps in knowledge: Pinpoint what your team doesn't yet understand about your users' goals, needs, and pain points.

• Segment your users: Choose specific user groups based on their type (e.g., repeat users), usage patterns, and lifecycle stage to focus your research.

• Create a targeted research plan: Plan your research methods—typically involving 1:1 user interviews—to deeply explore user motivations and barriers.

• Prioritize insights and take action: Analyze findings, prioritize key insights, and develop actionable recommendations to improve retention.

Learn more about Retention Research!

Want some real-life examples? 

Aakash Gupta, former VP of product at Amplitude, spent 15 years of his career working on improving retention rates - so he might know a thing or two. 

Along the way, Aakash helped:

• Fortnite increase 30D retention by over 10%.

• thredUP increase CLV by over 40%.

• Affirm increase TPU by over 50%.

How did he do it?!

Learn how to improve retention

What cannot be measured, cannot be improved 

So first - learn how measure your retention: 

1. Isolate Cohorts: Group users by meaningful segments (e.g., acquisition channel, region, or signup date).

2. Define Active Users Clearly: Identify specific actions that truly signify user engagement (e.g., loading into a game for Fortnite, or completing a ride for Uber).

3. Choose an Appropriate Timeframe: Select daily, weekly, monthly, or yearly retention measurements aligned with your product’s natural usage cycle.

Now - wanna improve it? Follow the Retention Hierarchy of Needs:

1. Core Value Delivery: Ensure your product consistently delivers clear value and has effective onboarding.

2. Engagement: Encourage regular usage through gamification, compelling features, or frequent value delivery.

3. Habit Formation: Integrate your product into users' daily routines or create new rituals around it.

4. Churn Prevention: Actively address voluntary (e.g., thoughtful cancel flows) and involuntary churn (e.g., payment recovery strategies).

Best Practices to Improve Retention:

• Personalized Welcome Flows: Customize onboarding based on user characteristics.

• Interactive Tutorials: Provide hands-on tasks that lead users directly to value.

• Progress Bars: Visually show users their onboarding progress to encourage completion.

• Onboarding Checklists: Clearly outline key actions new users should complete.

• Contextual Help Bubbles and Tooltips: Offer help exactly when and where users need it, reducing frustration and friction.

Read more about improving retention

What about...us? 

Inside Userpilot’s Retention Strategy: What’s Driving High User Stickiness

I wish  I could say "there's nothing to improve" - but even tools like Userpilot have to work to earn a 99%+ NRR. 

Luckily, we have Matt - our Head of Customer Success - who thinks about it night and day - treats retention as a...growth tactic. And so does our whole company. 

This is how we consistently hit 99%+ retention rate: 

• We focus on strengthening customer relationships across the entire lifecycle, addressing gaps to ensure consistent value delivery at every interaction.

• We prioritize clear accountability and information transfer by using structured success plans (via Dock), ensuring context isn't lost when users transition between teams (e.g., sales to onboarding to customer success).

• By applying these strategies, we've improved our Net Revenue Retention (NRR) by 2% over the past 8 months.

• We engage customers strategically, segmenting accounts based on priority and health score to tailor communication effectively and proactively.

• We emphasize delivering measurable value and ROI, moving beyond reactive support toward strategic customer enablement that directly addresses customer goals and pain points.

• We leverage enhanced system visibility and analytics through tools like Userpilot and HubSpot, allowing us to detect and respond to customer needs quickly and effectively.

By applying these strategies, we've improved our Net Revenue Retention (NRR) by 2% over the past 8 months.

Learn how straight from Matt's mouth!

And if they wanna cancel...make it hard. 

But "hard" doesn't mean "frustrating". 

Dr Bart Jaworski explained it all in his recent post: Making your cancellation flow intentionally challenging—but respectful—helps you retain users without breeding resentment. By thoughtfully adding value (like data exports or helpful alternatives), requesting optional but quick feedback, offering accessible support, and avoiding frustrating patterns (like hidden buttons or mandatory surveys), you ensure users leave with positive feelings toward your brand, preserving the relationship for possible future returns or recommendations.

• Add value during cancellation: Provide helpful options, such as data exports or personalized alternatives, that may encourage reconsideration.

• Ask for feedback (without forcing it): Use short, optional exit surveys to gain insights without frustrating users.

• Offer accessible support: Make help available without requiring lengthy calls or mandatory interactions, respecting user autonomy.

• Avoid annoying patterns: Don’t hide buttons, create deliberate obstacles, or manipulate users—these breed resentment and hurt your reputation.

• Don't train manipulation: If offering discounts or incentives, do so sparingly and transparently, ensuring users don’t feel incentivized to threaten cancellation repeatedly.

Learn about the art of product cancellations

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And that's it for this month's edition of the PITT - hope you've enjoyed this data-packed edition!

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