Filling the leaky bucket: How to make retention your secret super power [Part 2]

Ignoring user retention is like filling a leaky bucket. Without addressing the cracks, no amount of filling it up (i.e. acquiring new accounts and expanding within existing ones) is futile. Further, acquiring a new customer can be five times more expensive than retaining an existing one​. Ultimately, retention is the difference between a product that simply exists, and a product that thrives. 

To uncover why retention should be every product manager’s obsession, we spoke with Ryan Salomon, Pendo’s senior director of product analytics. In part 2, Salomon shares insights on how AI can improve retention, tips to build a company-wide culture around this KPI, and how regularly you should be monitoring user retention. 

This is part 2 of our interview with Ryan Salomon. Catch up on part 1 of his insights here. 

Q: How can AI help you improve user retention?

A: AI is a game-changer for retention. With predictive analytics, you can identify at-risk users before they churn. You can also use AI to personalize the user experience (UX), giving each user the in-app content and features that are most relevant to their roles, company, and behavioral data. AI/ML tools can also optimize timing for engagement prompts or reminders, nudging users back into the product in a meaningful way. 

At Pendo, we’re using AI to uncover hidden patterns in retention data that aren’t immediately obvious so we can be more proactive with our retention efforts.

Q: What surprising insights have you personally uncovered in retention data?

A: Small tweaks can lead to dramatic changes in retention. At Pendo, we discovered that users who interacted with a specific in-app feature within their first week were 40% more likely to stay after three months. We used that insight to adjust our onboarding flow and guide users to this feature earlier. The result? A significant boost in our overall retention rate.

Want more? Read our how-to-guide on building an effective in-app onboarding strategy.

Q: What advice would you give product leaders just starting to focus on retention?

A: Start by making retention a visible, everyday focus for your team. Conduct cohort analyses to see how retention changes over time and identify patterns. Experiment with changes in onboarding, feature placement, and in-app messaging, and always measure this impact on retention. 

You also need to make retaining users a shared goal. It’s about getting everyone—from product teams to executives—obsessed with the idea that every user interaction should add value and make them want to stay. If everyone is aligned around improving retention, you’ll see more collaboration and creative solutions.

Q: How would you build a culture around retaining customers?

A: I’m all for creating visibility and encouraging a little bit of friendly competition between product teams. We’ve become a little competitive with our dashboards at Pendo—team members are always showing off their dashboards and how they’re tracking key metrics. When you create an environment where people are proud of their data and actively engage with it, you make retention a team sport. It’s no longer just a product metric. Rather, it becomes a cultural focal point that people get excited about. 

Pro tip: Product teams can use readymade, expert dashboard templates in Pendo that include an automated retention report.

Q: How do you improve cross-functional collaboration by focusing on retention?

A: When retention is a shared goal, it breaks down silos. Marketing knows what types of users stick around longer, product knows which features drive retention, and customer success knows where users are struggling. Everyone brings something to the table, and the collaboration becomes natural and organic. It’s no longer about different departments with different goals; it’s about one unified company goal—keeping our customers happy and engaged.

Q: What habits or rituals should product leaders build around retention?

A: Make it a habit to review retention data in every team meeting. Create dashboards that are easily accessible and visible to everyone. Celebrate retention wins. If a team improves a feature that significantly boosts retention, acknowledge it. 

Make retention a part of your product development process; before building anything new, ask how it will impact retention. These habits keep everyone aligned and focused on what matters most: delivering value that keeps users coming back.

Retention is more than a metric—it’s a mindset. By making retention a focal point, product leaders can unlock sustainable growth, foster customer loyalty, and turn users into advocates. Stop filling a leaky bucket, and turn retention into your biggest growth driver. Get a demo to learn more.