Do You Have a Strategy to Retain Users?

From the Jason Calacanis startup checklist.

Retention is one of the most important levers in a product. The best retention strategies don't feel like marketing — they feel like the product doing its job.

Personalised Re-engagement

LinkedIn is a great example. After a few days without logging in, they send an email that doesn't say "we miss you" — it says "80 people viewed your profile." That's a personalised, curiosity-driven nudge that gives you a specific reason to return. When you open the app, you can see exactly who was looking.

Twitter/X does the same with push notifications. If you haven't logged in for a few days, you might get: "Bill Gurley and Knicks Film School are tweeting — don't miss it." They know what content you engage with most and surface that specifically. Generic notifications are ignored; personalised ones drive action.

The pattern in both cases:

Identify a moment of lapsed engagement
Deliver a personalised, curiosity-driven prompt
Make the reward (the content) immediately accessible when the user returns

Customer Success

In-app re-engagement is one side of retention. Customer success teams are another — particularly in B2B SaaS. Many users want a human touch: someone to check in, answer questions, and help them get more value from the product. As you grow, consider where a human layer could meaningfully reduce churn.