Your AI CEO turns dead trials into a recurring revenue line.
You'd think this needs a marketing ops hire — Astra runs the entire win-back loop on Stripe, PostHog, and your existing Mailchimp.
Astra 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.
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.
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.
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.
Stagger sends across 5 days to avoid inbox flooding. Honor unsubscribes. Skip anyone who churned in the last 14 days (too soon).
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.
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.
One-shot recovery campaign; repeatable quarterly as new trials accumulate.
We'll spin up your workspace, hand the prompt to Astra, and you see the answer in 60 seconds. Free.
Try this with AstraClear answers about wallet credit, usage, subscriptions, and how Tycoon charges for work.
Astra caps the lookback at 180 days by default — anyone older typically has zero recall of your product and reactivation rates drop below 1%. You can override ("go back 12 months") but Astra will warn that incremental ROI is usually negative past 6 months.
Astra works with whatever event source you have — Mixpanel, Amplitude, raw server logs, or even just Stripe events. With Stripe alone she can do Stage 1 and 4 well; Stage 2 and 3 need product event data to identify the aha moment correctly.
Yes — Astra proposes defaults (25% off, free month, extended trial) but waits for your sign-off before sending. You can override per segment, e.g. "no discount on Stage 3, just a Loom from me" — she rewrites that segment's copy in 30 seconds.
Astra honors it instantly — adds them to your suppression list across all future Astra-managed campaigns (not just this one) and confirms in Lark. Your Mailchimp unsubscribe link is also embedded in every email per CAN-SPAM/GDPR compliance.