Founder Playbook
Retention
“If you have a discounted plan inside your subscription group, Apple will automatically offer it as a downgrade option in the cancellation flow. You get a win-back path for free — without building any custom cancel flow infrastructure.”
Add a discounted plan to your subscription group — it becomes a built-in win-back in the cancellation screen
Moore surfaced an underused App Store mechanic: when a user initiates cancellation, Apple's native cancellation sheet can present a lower-tier or discounted plan if one exists in the same subscription group. This creates a passive win-back that requires zero engineering — just product configuration. Adding a $2.99 annual plan next to a $9.99 annual plan effectively creates a price-sensitive churn hedge inside Apple's own UI.
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Jake Moore & Darryl Stone
Superwall & CitizenJake Moore: Superwall founder, built Fitness AI through YC; moving paywall before onboarding + adding video lifted trial conversions 80% and install-to-paywall from 40% to 85%.
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Top 5 Considerations for Paywall Optimization — Live at App Promotion Summit NYC· 30:03