Premium GTM Situation
Win-Back Campaign
Re-Engagement. Acknowledge Change. Low-Pressure Return.
Purpose-built for churned accounts and dormant opportunities. Honor the past relationship, show what's changed, and make coming back feel like the right move—not an awkward one.
"The goal of a win-back campaign isn't to convince them they were wrong to leave. It's to show them that coming back is the right decision today."
— Re-Engagement Best Practices
Win-Back Principles
| Principle | What It Means | Avoid |
|---|---|---|
| Acknowledge | Honor the relationship and their decision | Pretending nothing happened |
| No Guilt | They had reasons. Respect them. | "We miss you!" desperation |
| Show Change | What's different now (you or them) | Same pitch that didn't work before |
| Low Friction | Make coming back easy | Big commitments upfront |
The Philosophy
Former customers aren't lost deals—they're people who trusted you once. The goal isn't to prove they were wrong to leave. It's to show them that coming back is the right decision today.
This requires humility. Acknowledge the relationship. Respect their decision. Show what's changed—either in your product or in their world. And make the return path feel natural, not desperate. The best win-backs feel like reconnecting with an old friend, not a sales pitch.
Key Characteristics
- →Acknowledge the history. Don't pretend it didn't happen. Honor the relationship.
- →No guilt-tripping. "We miss you!" is desperate. Respect their decision.
- →Show what's changed. New features, new approach, or new situation. Something is different.
- →Low-friction return. Conversation, not commitment. Make saying yes easy.
- →Human first. Write like you're catching up with someone, not selling to them.
When to Use
Best For
- • Churned customers (especially if you've improved)
- • Dormant opportunities that went cold
- • Lost deals approaching contract renewal
- • Customers whose situation has changed
Avoid When
- • Churn was due to serious trust breach
- • Nothing has actually changed
- • They explicitly asked not to be contacted
- • Very recent churn (give it time)
The Prompts
Win-Back Email
Write a win-back email for a churned customer. Context: - Former customer: [NAME], [TITLE] at [COMPANY] - Why they churned: [REASON IF KNOWN - budget, competitor, need changed, etc.] - How long since they left: [TIME PERIOD] - What's changed since: [NEW FEATURES, APPROACH, OR THEIR SITUATION] - Signal for re-engagement: [What triggered this outreach] Win-Back Email Rules: - Acknowledge the relationship. Don't pretend it didn't happen. - No guilt-tripping. They had reasons. Respect that. - Show what's changed—either in your product or their situation. - Make coming back feel low-friction, not awkward. - Don't assume they remember everything about you. - Fresh start framing > "we want you back" desperation. - Low-pressure ask: conversation, not commitment. - Under 100 words. Warm, not needy. Tone: Warm, humble, genuinely curious about their situation. Like reaching out to an old colleague.
Win-Back Discovery Questions
Generate win-back discovery questions. Context: - Former customer: [COMPANY] - Why they left: [REASON IF KNOWN] - Time since churn: [PERIOD] - What's changed: [YOUR IMPROVEMENTS OR THEIR SITUATION] Win-Back Discovery Approach: UNDERSTANDING THE DEPARTURE - Help me understand what led to the decision to move on? - What were you hoping to find that we didn't provide? - Was there a specific moment or issue that tipped the decision? CURRENT STATE - How has [their solution area] evolved since we last spoke? - What are you using now? How's it working? - What's different about your needs today vs. then? OPENNESS TO CHANGE - What would need to be true for you to consider a change? - Is this something you're actively thinking about, or is timing bad? - Who else would need to be involved in a conversation like this? WHAT'S CHANGED (on your side) - Here's what we've improved since you left... [be specific] - Does any of that address what drove the original decision? Listen more than you pitch. They chose to leave for a reason.
Win-Back Objection Handling
Handle this objection in a win-back conversation. The objection: [PASTE OBJECTION HERE] Context: - Why they churned originally: [REASON] - What's changed since: [IMPROVEMENTS] - Their current situation: [WHAT YOU KNOW] Win-Back Objection Framework: - "We're happy now" = Respect it, but stay in touch - "It didn't work for us" = Acknowledge, share what's changed, don't defend the past - "We've invested in [competitor]" = Understand the commitment, find the wedge - "Timing isn't right" = Agree, establish future touchpoint Generate: 1. Acknowledgment without defensiveness 2. Question to understand current state 3. What's changed (brief, relevant) 4. Low-pressure next step or permission to stay in touch
LinkedIn Message
Write a LinkedIn message to a former customer. Context: - Former contact: [NAME], [TITLE] - Their company: [COMPANY] - How long since you worked together: [TIME] - Trigger for outreach: [WHAT PROMPTED THIS] Win-Back LinkedIn Approach: - Acknowledge the history. Personal > professional. - Don't immediately pitch. Re-establish the relationship. - Show genuine curiosity about their current situation. - If appropriate, share something valuable (not salesy). - Only ask for a conversation if there's a genuine reason. - Under 50 words. Warm, not transactional. Tone: Like catching up with someone you used to work with. Human first.
Win-Back Sequence Builder
Create a win-back email sequence for churned accounts. Context: - Target segment: [WHO ARE THESE CHURNED CUSTOMERS] - Primary churn reason: [WHY THEY LEFT] - What's changed: [PRODUCT IMPROVEMENTS OR MARKET CHANGES] - Goal: [RE-ENGAGEMENT MEETING / TRIAL / DEMO] Generate a 4-email sequence: EMAIL 1: The Acknowledgment - Acknowledge the relationship - Show you remember them (personalization) - No pitch—just genuine check-in - Ask about their current situation EMAIL 2: The Update (2-3 days later) - Share what's changed since they left - Be specific and relevant to their churn reason - Make it about them, not you - Soft ask: "Worth a fresh look?" EMAIL 3: The Value Add (1 week later) - Share something useful (no strings attached) - Industry insight, benchmark data, or resource - Show you're thinking about their success, not just the sale - "Thought of you when I saw this..." EMAIL 4: The Graceful Close (1 week later) - Last touch for now - Clear permission to re-engage later - Leave the door open - "I'll leave you alone unless you say otherwise..." Each email should be under 100 words. Warm, not desperate.
Example Output
Subject: Been a while Sarah, It's been about 18 months since Acme moved on from us. Totally get why—at the time, the integration gaps were a real blocker. Quick update: we've rebuilt the entire data pipeline since then. Specifically solved the Salesforce sync issue that I remember being painful for your team. Not sure if you're still dealing with pipeline data challenges, but if you are, might be worth a fresh conversation. Either way, hope all is well with the team. — Marcus