| name | trial-to-paid-converter |
| description | Design a trial-to-paid conversion playbook with usage-personalized nudges (in-app + email) timed to the trial countdown. Use when the user says "increase trial conversion", "trial-to-paid flow", "convert more free users", or is launching a new trial. |
| status | new |
Trial-to-Paid Converter (Revenue Squad)
Builds the in-trial experience. Every nudge is personalized to what the user has (or hasn't) done so far.
Triggers
- "increase trial conversion"
- "trial-to-paid flow"
- "convert more free users"
- "what should we email trialists"
- "redesign the trial"
Inputs required
- Trial length โ 7, 14, 30 days
- Trial type โ opt-in credit card, reverse trial, freemium with time-limited features
- Activation event โ from Aha-Moment Mapper
- Current trial-to-paid rate (if known)
- Feature access โ what's locked in trial vs. paid
- Event data โ so we can personalize by actual usage
Process
Step 1 โ Pick a trial archetype
- Opt-in (card required) โ highest CVR, lowest signup
- Reverse trial โ full product for 14 days then downgrade to free
- Freemium with time-locked features โ lowest friction, hardest to convert
Recommend one based on ICP + AOV. Note tradeoffs.
Step 2 โ Segment trialists by usage signal
At each check-in point (day 1, 3, 7, trial-end):
| Segment | Signal | Right message |
|---|
| Activated | Hit aha event | "Here's what advanced users do next" |
| Trying | Some activity but not aha | "You're close โ try this one thing" |
| Ghosts | Signed up, did nothing | Reactivation hook or archive |
| Power | 3x normal usage | Upgrade nudge early + account manager reach-out if value tier |
Step 3 โ Design the in-trial flow
Per segment, per day, specify:
- In-app: banner, progress bar, tooltip, or modal
- Email: subject + body + CTA
- Sales touch: only for power users above ARR threshold
Critical beats:
- Day 0: Welcome + checklist to aha
- Day of activation: "Congrats โ here's what's possible"
- Day before trial end: Show value delivered + upgrade CTA with total
- Trial end day: Upgrade prompt + easy path to extension (maybe 7 days) if they ask
- Day after trial end: One last email with value recap + compelling offer
Step 4 โ Price anchoring during trial
- Show plan they're on if upgraded
- Show total saved with annual
- Show features they're using that they'll lose if they don't upgrade
- Avoid loss-aversion hammering โ once, not five times
Step 5 โ Declare hypothesis + metric targets
- Primary: trial-to-paid rate
- Guardrails: trial-end unsubscribe rate, post-trial NPS
Hand to A/B Test Designer for structured test.
Output artifact
trial-conversion-playbook.md with:
- Archetype recommendation
- Per-segment ร per-day matrix
- Copy for every message (in-app + email)
- Sales touch rules
- Metrics spec
Handoff
- In-app โ product / design
- Emails โ Lifecycle Email Designer runbook
- Sales touches โ sales ops
- Trial-end upsells โ Upsell Sequencer
Example call
"We have a 14-day trial with card required. Trial-to-paid is 18%. ICP is RevOps at 50โ500 person SaaS. Activation is 'connect a data source AND build a first report'. Help me redesign the trial experience."
