Re-engagement & Win-back Campaign

The first 10 questions

This is where the conversation starts. Each answer shapes what gets asked next.

1. 01Who are you trying to bring back — a specific cohort that churned recently, or users who went dormant without formally canceling?
2. 02Do you know why they left — cancellation survey data, support tickets, or just a guess?
3. 03Has anything changed in the product since they left that's actually relevant to winning them back?
4. 04What are the distinct segments within 'churned/dormant' — price-sensitive, never activated, outgrew you, found a competitor — and do they need different messages?
5. 05What's the real reason to reach out now versus leaving them alone — a new feature, a pricing change, a genuine improvement?
6. 06What's the line between 'thoughtful re-engagement' and 'annoying spam that gets you reported' for this audience?
7. 07What offer, if any, are you willing to make — discount, extended trial, personal outreach — and what's the cost/risk of that?
8. 08Segment-specific messaging: the distinct message for each churn segment you identified.
9. 09Sequence: how many touches, over what timeframe, and what changes message-to-message?
10. 10Subject lines / opening lines: the specific hooks for each message in the sequence.

+ 5 more questions across discovery, validation, and the creative brief — each one adapting to what you've already said.

Related marketing project types

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• Name Your StartupChoose a name you can defend, spell out loud, and actually own — working from positioning criteria rather than word games, with live domain checks on the shortlist.
• Competitive PositioningMap your competitive landscape, find the position that's genuinely yours to own, and build the case for why your approach beats the alternatives for the customers who matter most.