Design a 3-email win-back campaign for customers who churned in the last 6 months. The goal is real re-activations, not a discount race.
BUSINESS: {SaaS / DTC / B2C_subscription / B2B_service}
WHO CHURNED + WHY (top 2-3 reasons): {top_reasons_from_exit_surveys}
HOW LONG SINCE THEY LEFT: {3-6_months}
THEIR EMAIL APPETITE before churn: {opens_a_lot / opens_rarely}
WHAT HAS CHANGED since they left (real changes): {new_feature / new_pricing / new_CS / nothing}
WHO SENDS THE EMAIL: {founder / CSM / brand_email}
INCENTIVES YOU CAN OFFER: {discount / extended_trial / free_migration / nothing — pure_reactivation}
WHO YOU DON'T WANT TO WIN BACK: {bad_fit_customers / chargebacks / abusive — they should NOT get this campaign}
DESIGN:
1. **Segmentation rule** — who's IN the campaign, who's OUT.
2. **Email 1 (day 0) — Honest re-introduction.** What they should know about what's new. No discount.
3. **Email 2 (day 7) — A genuine value moment.** A single useful piece of content / case study, no pitch.
4. **Email 3 (day 14) — Open the door.** Specific offer if relevant, clear out-clause.
5. **What you measure** — not just 'reactivation rate' but quality (did the reactivated customer stay 3+ months?).
6. **The unsubscribe play** — make it easy. Trying to retain people who've moved on damages your brand.
7. **One 'red flag' segment NOT to email** — the people you should let go.0 copies·0 saves·2 views
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Sample output
Business: B2B SaaS, $99/mo plan. Top churn reasons: (1) team consolidation onto a different tool; (2) onboarding never landed; (3) price increase 9 months ago that they didn't accept. Time since leaving: 4-6 months. Email appetite: mixed. What changed: new onboarding flow with assigned CSM for all paid plans, plus a new 'starter' tier at $49/mo. Sent by: CSM (not founder). Incentives: can offer 1 month free + free re-onboarding session. Don't want back: customers who chargeback or violated ToS.
1. Segmentation:
IN the campaign:
OUT:
Parameters
Text generation parameters
FAQ
Win-back campaigns are 'audience pruning' as much as 'reactivation'. The unsubscribes you get tell you who you definitively can't have back — and frees you to focus on new acquisition for them. The prompt targets Claude Sonnet and lives in the Marketing & Sales category on mycopyprompt.
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2. Email 1 — Day 0 — Honest re-introduction
Subject: Quick update on what's changed since you left
Hi [Name],
I'm [CSM Name] — the customer success team at [Company]. I noticed you canceled your account 4 months ago, and I wanted to drop you a note with the things that have actually changed since then. No pitch.
Two things that might matter:
We rebuilt onboarding. Every paid customer now gets an assigned CSM (like me) and a 45-min setup session in week 1. The 'I never quite got it' onboarding problem was real, and the data shows we've fixed most of it.
We launched a Starter plan at $49/mo (down from our previous floor of $99). If price was part of why you left, that may be worth knowing.
That's it. No call-to-action — just wanted to keep you informed.
If you ever want to come back, we'd love to have you. If not, no hard feelings.
Best, [Name]
3. Email 2 — Day 7 — A useful thing
Subject: For when you're tackling [their challenge again]
Hi [Name],
Quick one. We just published a piece on [tactical thing — e.g. 'how 3 mid-market teams cut their onboarding time from 2 weeks to 3 days']. It's not about us — it's about how three different teams (using our product and one competitor) actually did it.
→ [link]
Thought of you because [genuine reason — your team was working on this exact problem].
No response needed. Just wanted to share.
[Name]
4. Email 3 — Day 14 — Open the door
Subject: Want to take a fresh look?
Hi [Name],
Last note from me. If you're open to it, I'd love to set up a 20-min call to walk you through what's changed and see if anything we've shipped this year would actually be useful for your team now.
If you want to come back, here's what I can do: a month free + a personal onboarding session with me. No commitment beyond that — you'd be on the same plan you'd been on before (or the new Starter, if that fits better).
If the answer is 'we moved on' or 'no thanks, just unsubscribe', that's totally fine — reply with either, and I'll respect it.
If I don't hear back, I won't email you again. Promise.
[Name]
5. Measurement:
Surface metric: % of segment that re-activates (clicks 'reactivate' link or starts a new subscription within 30 days of email 3).
Real metric: of those who reactivate, what % stay paying for ≥ 3 months. That's the only metric that matters — anything else is a false reactivation that churns again.
Cohort tracking: segment by why they originally churned. 'Price' churners reactivate at one rate; 'team consolidation' churners at another. Don't average them.
6. Unsubscribe:
7. Red-flag segment — DON'T email:
Customers who explicitly told you (in exit interviews or support tickets) that the product had a security or data-integrity issue. Win-back emails to them feel tone-deaf. These customers need a personal email from the founder or head of product addressing what specifically was fixed — and only if you can credibly say it was fixed. A generic 'we've updated some things' campaign damages your reputation.