How to build a win-back campaign that actually works
- Raymond Otero
- Jun 9
- 1 min read
Source article: How to build a win-back campaign that actually works

🧭 Key Takeaways:
1. Win-back campaigns are about trust, not desperation. Raymond Otero, Director of Global Customer Experience at Microsoft, shares a personal story of customer churn during a digital transformation project. The failure wasn’t due to technology but a breakdown in customer experience. This led to a strategic win-back campaign that successfully re-engaged customers and turned them into advocates.
2. Why win-back campaigns matter more than ever:
Retaining customers is significantly more cost-effective than acquiring new ones.
Returning customers often have higher lifetime value.
A Bain & Company study shows that a 5% increase in retention can boost profits by 25% to 95%.
3. The 5-part framework for a successful win-back strategy:
Understand the “why” behind churn: Use exit interviews and usage data to identify root causes.
Segment and prioritize: Focus on high-value or high-potential customers.
Craft personalized messaging: Tailor outreach based on customer history and pain points.
Deliver renewed value: Offer something meaningful—new features, better support, or exclusive offers.
Measure and iterate: Track performance and refine the approach continuously.
4. The mindset shift: Win-back campaigns should be seen as an opportunity to re-earn trust and demonstrate renewed value, not just a sales tactic.
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