Configure subscription trials

Configure subscription trials in Stripe — with the four heights of help laid out: do it now, make it easier for the next person to accept, work out the right move when you are stuck, and learn the pattern so it stops coming back.

4prompt heights
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The four heights

The same task, four distances: today's deadline, the next reviewer, the stuck moment, the pattern.

Execute — do the immediate task

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We want to offer a 14-day trial on our Pro subscription without collecting payment details.…
We want to offer a 14-day trial on our Pro subscription without collecting payment details. Configure the subscription so new signups enter a trial period of 14 days, then convert automatically to the paid Pro plan unless the customer cancels. Ensure trials are only allowed once per customer email, show how to manually grant or revoke a trial, and list where to see all active trials. Ladder":"L1"

Improve — make it easier to accept

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Before I roll trials live, make the experience approval-ready: show the trial duration and…
Before I roll trials live, make the experience approval-ready: show the trial duration and conversion date prominently in signup emails, provide a sample cancellation flow so support can guide customers, display how trials appear on the customer account page, and flag three risks that make finance nervous (accidental auto-charges, trial users gaming entitlement, or fraud). Ladder":"L2"

Decide — diagnose the stuck moment

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Marketing wants to require a card to reduce trial abuse; product wants frictionless signups to grow…

We don’t know whether to require a card for trial signup.

Marketing wants to require a card to reduce trial abuse; product wants frictionless signups to grow MQLs. I don’t know which will give better conversion to paid accounts without sacrificing acquisition. Given our price point and history of credit-card fraud attempts, what would you recommend as the default trial flow and what guardrails (limits, verification, rate limits) should we add if we don’t require cards? Ladder":"L5"

Become — change the pattern

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Over multiple product launches, trials either convert at low rates or create heavy support costs…

Trials convert poorly and cause support churn.

Over multiple product launches, trials either convert at low rates or create heavy support costs when people expect paid features. We need a repeatable trial policy that increases conversion and reduces abuse. Recommend three changes to trial design, onboarding, and monitoring: how to set trial length, whether to require payment methods, and what signals should trigger manual review or conversion nudges. Ladder":"L6"

Next to this one

Other payments work people do in Stripe.

Every task here came from the work, not from a feature list — which is why the prompts name what you want done and never the button that does it. The tool changes; the work does not.
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The rest of the map

Same library, five ways in.