Ledgerly: cancel flow and failed-payment recovery plan

Baseline math (per 1,000 subscribers)

I assumed the one-third figure is net of whatever Stripe's defaults already recover today. If you have gross failure counts, I can re-baseline.

Targets at 90 days: involuntary 2.0% → ~1.2%, voluntary 4.0% → ~3.2%, total 6.0% → ~4.4%. That is roughly a 27% cut in churn. Treat these as hypotheses to test, not promises.

Part 1: Voluntary cancel flow

Flow: Settings → Cancel → one-question survey → one matched offer → confirm → post-cancel.

Survey

Title: "Help us improve: what's the main reason you're cancelling?" It is single-select with optional free text. Options, ordered by expected frequency (re-sort quarterly):

1. Too expensive
2. Not using it enough
3. Missing a feature I need
4. Switched to another tool
5. Bugs or technical issues
6. Don't need it right now
7. Business closed or changed
8. Other (free text)

Every screen has a visible "Continue cancelling" button, and the survey is skippable.

Offer matrix ($29 plan)

Guardrails

• One primary offer and one fallback per reason. Never show a wall of options.
• Discount cap is 30%. Allow one discount per account per 12 months, so people can't cancel repeatedly for deals.
• Pause is capped at 3 months.
• No guilt copy, no countdown tricks, and no confirm-shaming on the decline button.
• Mobile-first layout, since many cancellations happen on a phone.

Confirmation and post-cancel

• Confirmation screen: "Your access continues until [date]. You won't be charged again." Include a one-click "Undo cancellation" link, and offer a data export.
• Cancel at period end via Stripe cancel_at_period_end.
• Send an immediate confirmation email with a reactivation link.
• Win-back sequence at day 7, 30, and 90 (see the emails skill). Day 30 is tied to the stated cancel reason, such as a feature-shipped notice.

Proactive layer (before they reach Cancel)

• Usage down 50% or more for 2 weeks → "Need help?" email.
• No login for 14 days → re-engagement email.
• Billing page or data export visits → flag the account as high risk.
• Renewal reminders are mostly unneeded for monthly billing. Use a value-recap email at month 3 and month 11 instead.

Measurement

• Cancel-flow save rate target: 20–25% of cancel sessions, with offer acceptance of 15–25%.
• Track 90-day retention of saved users separately. A save that cancels 30 days later doesn't count.
• Pause reactivation target: 60%+.
• First test: discount depth (20% vs 30%) and pause length (1 vs 3 months). Run one variable at a time, with feature flags such as PostHog if you use it.

Part 2: Failed-payment recovery (about 1/3 of churn)

Pre-dunning (prevent failures)

• Turn on the Stripe card account updater (automatic) and Smart Retries.
• Send card-expiry emails at 30, 15, and 7 days before expiry.
• Ask for a backup payment method after the first successful renewal, not at signup.
• EU: offer SEPA Direct Debit at checkout. It has far fewer expiry-related failures than cards.
• EU: use setup_future_usage=off_session with SCA/3DS at signup so renewals are exempt where possible.

Retry logic by decline type

Keep total retries well under card-network limits.

Dunning email sequence (plain text, transactional)

• Also show an in-app banner and a lock-on-login prompt from day 0.
• Optional SMS or push at day 5 for users who opted in (only where consent exists).
• Language: "your payment didn't go through", never "you failed to pay".
• Use localized currency and language for EU customers.
• When a customer fixes their card, retry immediately instead of waiting for the next scheduled retry.

Grace period and end state

• Keep access (read-only after day 7) through day 10–14.
• After that, cancel the subscription but keep data for 90 days with a one-click reactivate link.
• Feed those users into the win-back sequence, tagged "payment failure", not "chose to leave".

Measurement

• Payment recovery rate target: 60%+ overall (soft 70%+, hard 40%+).
• Pre-dunning prevention target: 20% of would-be failures.
• Track involuntary churn as a separate line item from voluntary churn.
• Report weekly during the first month: failures, recoveries by decline code, and email-to-update conversion.

Compliance (US and EU)

I'm not a lawyer. Have counsel review before launch.

• US: keep online cancellation as easy as sign-up. The federal FTC click-to-cancel rule was struck down in 2025, but state automatic-renewal laws (California, New York, and others) still require easy online cancel and clear renewal disclosures. This flow's single survey, one offer, and visible exit is built to satisfy that.
• EU: a clear "cancel contract" function is required in Germany and is increasingly expected elsewhere. The EU consumer-rights withdrawal-button requirement is phasing in during 2026. Keep the cancel path to a few clicks, with no forced survey.
• GDPR: dunning and cancellation emails are transactional. Win-back marketing needs a lawful basis or consent in the EU, so gate it accordingly.
• PSD2/SCA: failed 3DS payments need customer action, which is why the authentication-required row above doesn't retry.

Rollout order

1. Week 1: enable Smart Retries, the card updater, and Stripe's built-in dunning emails. Add SEPA for EU customers. Tag decline codes.
2. Week 2: replace the default emails with the custom 4-email sequence and add the in-app banner.
3. Weeks 2–4: build the cancel flow with the survey and the "too expensive" and "not using" offers first (the likely top two reasons), plus pause.
4. Month 2: add the remaining reason paths, win-back emails, and the proactive risk emails.
5. Month 3: start A/B tests and review save-offer LTV.

You can build the cancel flow in-house with the Stripe Billing Portal and a small custom screen, or buy Churnkey or ProsperStack. At $29/month, buying is probably faster if you have under a few thousand subscribers.

Next, I can draft the dunning email copy, the cancel-screen copy per reason, or the Stripe configuration and webhook handling. Tell me which you'd like first.