The uncomfortable truth about churn

We often talk about “reducing churn” like it’s a dashboard problem. It isn’t. Churn is a conversation with a customer who’s trying to do their job under constraints you can’t see. The emails below aren’t magic words. They’re invitations to reply.

1) Payment failed (dunning #1)

Subject: “Card hiccup — we’ll keep everything safe”

Body:

Hi {{first_name}},

We couldn’t process your last payment for {{product}}. Nothing’s lost — your data and settings are safe.

Here’s a quick link to update your card: {{billing_link}}

If it’s a bank issue, hit reply and I’ll extend your grace period.

— {{signature}}

Timing: Send immediately. Tone: calm, helpful.

2) Payment failed (dunning #2 — empathy + friction reducer)

Subject: “Quick fix: update card without logging in”

Include a magic link token to billing so they skip password friction. This alone recovered ~18% of our failed payments.

3) Inactivity nudge (When value is hidden behind setup)

Subject: “Took me 2 mins to set this up for you”

Body:

Hey {{first_name}},

I noticed you haven’t connected {{integration}} yet. I recorded a 60‑second clip showing the exact steps on your account: {{loom_link}}.

If you want, reply with the API key and I’ll wire it up now.

— {{signature}}

This offers done‑for‑you momentum. Unblock, don’t lecture.

4) Silent success (Celebrate small wins)

Subject: “You shipped again this week — high five”

Send when a user completes a key action twice. It cements the habit and makes cancellation feel like losing progress.

5) Pre‑cancellation checkpoint (Save the exit interview)

Trigger this before they hit “Cancel” — when they open billing or export data.

Subject: “Can I fix this before you go?”

Body:

No forms, just this reply box. If something’s slow, confusing, or missing, describe it and I’ll get you an answer today.

This email saved two enterprise accounts for us — both had tiny, solvable blockers.

6) Cancellation survey (One screen, one question)

Show a single required question in‑app: “What nearly made you stay?” Add 5 quick‑select reasons and one free‑text box. Then send this follow‑up:

Subject: “Thanks — one last thing from me”

Body:

I read your note about {{reason}}. Two options that have helped teams like yours:

1. Switch to annual at a flat discount
2. Downgrade to {{lower_plan}} and keep {{critical_feature}}

If either helps, reply and I’ll flip the switch.

7) Winback (60–90 days later)

Subject: “Since you left: what changed in {{product}}”

Include 3 concrete updates and a short video walkthrough. End with a time‑boxed offer (e.g., “return on annual at your old price for 48 hours”).

Implementation notes (Laravel + Stripe)

• Use Stripe’s billing_portal.sessions.create and pass a return URL so people aren’t stranded.
• Send dunning from your domain, not a third‑party sender, to improve reply rates.
• Log replies in your app (simple conversations table) so teammates see context.

If billing itself is the pain, fix that first. I documented 12 gotchas here: Stripe + Laravel Subscriptions: 12 Gotchas I Hit and How I Fixed Them.

For broader launch hygiene, check the SaaS Pre‑Launch Checklist and our Go‑to‑Market Strategy Checklist.