Win back customers who left

What it does

The people who cancelled already know you, already had the problem and already paid you once. Many left for a reason that has since changed: a feature you’ve now built, a budget freeze that’s over, a champion who’s been replaced, or onboarding you’ve fixed. After your customers, they’re the warmest list you have, and most founders never write to them.

What you need

• Your cancelled customers from the last two years, from your billing tool
• Why they left: cancellation answers, last emails, support tickets and CRM notes
• A list of what you’ve built or fixed since

How it works

1. 1

   List everyone who left

   From Stripe or your billing tool: the company, the contact, when they started and cancelled, and what they paid.

2. 2

   Find the real reason for each one

   Prompt for Claude or ChatGPT, with what you have on them attached

   Here's what we have on [NUMBER] customers who cancelled: their cancellation answers, last emails, support tickets and notes.
   
   For each one, give me the main reason they left, in one line, with a quote that shows it. Use one of: missing feature (say which), price, champion left, budget or timing, poor results, poor onboarding or support, went out of business, other. If it isn't clear, write "unclear". Don't guess.

3. 3

   Match each reason to what’s changed

   Is the reason still true? A feature you’ve built, onboarding you’ve rebuilt, a new plan that fits their size, a budget freeze that ended. If nothing has changed for a reason, leave those customers alone for now.

4. 4

   Write to the ones whose reason has changed

   Email: name the reason and what changed

   Subject: [WHAT CHANGED, IN 2 TO 4 WORDS]
   
   [FIRST NAME] - when [COMPANY] left us in [MONTH, YEAR], it was because [THE REASON, IN THEIR WORDS]. Fair call.
   
   Since then, [WHAT CHANGED, IN ONE LINE].
   
   Worth a fresh look?
   
   [YOUR NAME]

   If your contact has moved on, write to whoever has the job now, and follow your old contact to their new company.

5. 5

   Check the rest every quarter

   Price and poor results don’t change with an email. Note them, fix what you can, and look again next quarter.

What good looks like

Every former customer has a reason next to their name, and the ones whose reason changed hear from you this month.

Mistakes to skip

• A generic “we miss you” email with a discount.
• Writing to people who left over poor results without changing anything.
• Trusting the reason on file. Read their last emails before you write.