Work-Bench is a NYC-based $160M enterprise software Seed stage VC fund. If you are or know anyone thinking about founding an enterprise/vertical AI or infrastructure startup - we’d love to meet! Please reach out to chat.
💡 THE TIP
One founder we know sends every churned customer a $50 Amex gift card and a handwritten note asking for 15 minutes of honest feedback. The gift is unconditional (they keep it regardless), but the gesture gets 68% of churned customers to agree to a call.
The insight here is subtle. Churned customers have already decided to leave, which means they have zero incentive to sugarcoat anything. But most companies never ask, or they send a survey that gets ignored. The gift card and handwritten note signal that you genuinely want to hear the hard truth.
Special shoutout to Todd Saunders from Broadlume for this tip! Check out his tweet on it here.
✅ THE TO-DO
Pull your list of customers who churned in the last 90 days. Pick five. Write each a short, handwritten note (three sentences max) thanking them for being a customer and asking for 15 minutes of honest feedback. Include a $50 gift card. Don’t pitch them on coming back. Just listen. Track what you hear and look for patterns after all five calls.
If you found this tip helpful, please share with a fellow b2b founder 😎
🤖 THE CLAUDE SKILL
Paste this into Claude to draft the outreach note, a discussion guide for the call, and a framework for synthesizing what you learn.
You are a customer success strategist. I run [COMPANY NAME], which sells [PRODUCT DESCRIPTION] to [TARGET CUSTOMER]. We recently lost [NUMBER] customers over the past [TIME PERIOD].
I want to send each churned customer a handwritten note with a $50 gift card asking for 15 minutes of feedback. Please generate:
1. A short, handwritten-style note (3-4 sentences max). Warm, genuine, zero sales pitch. The gift card is unconditional. I just want their honest perspective.
2. A 15-minute discussion guide with 5 open-ended questions designed to surface:
- The real reason they left (not the official reason)
- What they switched to (if anything) and why
- What would have changed their mind
- What they'd tell a friend about the product
3. A simple synthesis template I can fill in after each call to track patterns across churned customers (a table with columns for: customer name, stated reason, real reason, switched to, what would have saved them, biggest surprise from the call)
Tone: curious and humble, not defensive. I want them to feel safe being blunt.Do you have a GTM protip? Send our way here to feature in an future issue! If you try any of these tips and found them helpful, let us know - we’d love to hear from you.