A complete behavioral email architecture — from first touch through retention and re-engagement. Every sequence is triggered by what users do, not just when they signed up.
| Sequence | Trigger | Emails | Key Message | Goal |
|---|---|---|---|---|
| Monthly Health Check | 30 days after trial converts to paid | 1 email from founder | "How is your community using HOAHelper? What would make it more useful?" — genuine curiosity, not survey | Identify at-risk accounts before they churn |
| Re-Engagement (Inactive) | 14 days of zero admin activity | 2 emails over 7 days | "We noticed you haven't logged in — here's what you're missing" with actual usage stats from other communities | Return inactive accounts to active usage |
| Win-Back (Churned) | Subscription cancelled | 3 emails over 30 days | Email 1: "Was it something we did?" (survey) · Email 2: Product update · Email 3: Final offer (1 free month to return) | Recover 10–15% of churned accounts |
| Annual Billing Push | 3 months on monthly billing | 1 email | "Get 2 months free — switch to annual billing" — clear math, one-click upgrade | Convert monthly → annual for retention lift |
| PM Expansion | Paying customer for 6+ months | 2-email sequence | "You've been a HOAHelper customer for 6 months — do you know any property managers who might benefit?" | Generate B2B referrals into PM pipeline |