Retarget every trial that dropped off
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.
The short answer
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.
How Astra actually does it
- 1Pull 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 - 2Segment 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.
- 3Write 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 - 4Send 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 - 5Route 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
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.
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Try this with AstraFrequently asked questions
What if some trials are too old to retarget?
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.
What if I don't have PostHog set up?
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.
Can I tweak the discount or offer per segment?
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.
What if someone replies "please remove me"?
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.
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