You'd think this needs a marketing ops hire — Tycoon Agent runs the entire win-back loop on Stripe, PostHog, and your existing Mailchimp.
The short answer
Tycoon Agent retargets trial drop-offs by joining your Stripe customer list against PostHog activation events, isolating users who started a trial but never paid, and segmenting them by where they fell off — never logged in after signup, used the product but didn't hit the aha moment, hit the aha moment but didn't enter card. For each segment she writes a different win-back email: "have you tried X yet" for the first, a feature reveal for the second, a discount or extended trial for the third. She sends via Mailchimp, suppresses anyone who unsubscribed, tracks opens and clicks, and routes anyone who clicks back into a sales sequence or auto-extends their trial. Typical recovery: 3-7% of dropped trials reactivate, and recovered users have 1.4× higher LTV than fresh signups.
How Tycoon Agent actually does it
- Pull and join the data
Stripe trial-started events ∩ PostHog session events ∩ Stripe paid customers (excluded). Output: list of trial drop-offs with last activity date and depth of usage.
StripePostHog
- Segment by drop-off stage
Stage 1: signed up, never logged in. Stage 2: logged in, low usage. Stage 3: hit aha, didn't pay. Stage 4: paid once, churned. Each gets a distinct message.
- Write segment-specific copy
Stage 1: re-onboarding nudge. Stage 2: feature reveal + 1-min Loom. Stage 3: 25% off first 3 months. Stage 4: "what would have made you stay" survey + offer.
Mailchimp
- Send and suppress
Stagger sends across 5 days to avoid inbox flooding. Honor unsubscribes. Skip anyone who churned in the last 14 days (too soon).
MailchimpComposio
- Route reactivations
Click → trial auto-extended 7 days + slack ping to you. Reply → routed to your inbox for personal touch. Conversion → tagged "win-back" in Salesforce for LTV tracking.
SalesforceLark
What it looks like in chat
YouRetarget every trial that didn't convert.
Tycoon AgentPulled from Stripe + PostHog: 1,847 trials started in the last 90 days, 312 converted (16.9%), 1,535 dropped. Segmenting: - **Stage 1 (signed up, never logged in)**: 487 — usually fixable with a single re-onboarding email + Loom. - **Stage 2 (logged in, low usage)**: 612 — feature they didn't discover is the unlock. - **Stage 3 (hit aha, no card)**: 298 — pricing objection, offer 25% off first 3 months. - **Stage 4 (paid, churned)**: 138 — "what would have made you stay" survey before any offer. Drafted one email per segment in Lark for your review. Sending Mon-Fri next week, 300/day, suppressing the 47 unsubscribes. Conservative projection: ~60-105 reactivations (4-7%), worth ~$11K-19K MRR. Approve copy?
What you get back
Four segmented email campaigns sent over 5 days, a Lark digest with daily opens/clicks/reactivations, trial extensions auto-applied, and a final retro on which segment had the best ROI.
Cadence: One-shot recovery campaign; repeatable quarterly as new trials accumulate.