Automate the lifecycle
The same emails you sent by hand in Phase 1, sent automatically and better.
Target: 6 automated flows live
Inside this
- Automate welcome and activation8h
Behaviour-triggered, not day-based. “Has not activated after 48h” beats “day 2”.
- Automate the trial-expiry sequence4h
Day −3, day −1, expiry day, day +3. The last one converts more than you expect.
- Build proper dunning4h
Card retries, an updater for expired cards and a short email sequence. Stripe’s own billing page says it recovered $8.2B in failed payments in 2025; read any recovery figure as the vendor’s own.
- Build the win-back sequence4h
Sent 30 and 90 days after cancellation, and only when you have actually shipped their reason.
- Put an upgrade prompt at the limit moment10h
When they hit the ceiling, not on a schedule. Context is the entire conversion rate.
- Automate the review ask after a win4h
G2 weights a review down from day one — gently for 90 days, hard after 18 months — so the Phase 2 count is already shrinking. Send the ask after the third win, once per user, never on a schedule.