Blog · Sales · 2026-08-30

Run a Six-Month Customer Win-Back Loop

Find recent cancellations, prepare personal outreach, track reactivations, and feed customer reasons back into product decisions.

Premise

A useful win-back campaign does more than send a discount. It finds every eligible former customer, personalizes a restrained message, records the response, and turns the reasons for leaving into structured feedback.

Setup

  1. Connect billing or product records containing cancellations from the last six months.
  2. Connect an email account and define opt-out rules.
  3. Set permitted offers, discount caps, and promises.
  4. Approve a template and five representative drafts before any batch send.

Boundaries

  • Suppressed and opted-out contacts are excluded.
  • Refunds, large discounts, and product promises require approval.
  • Every send and response must be logged.

Draft a personal message in my voice for each eligible person. Keep it under six sentences, avoid canned greetings, and make one clear request: consider returning or share why the product no longer worked. Show me the template and five varied examples before sending anything.

After approval, track sent, delivered, bounced, replied, reactivated, and reason supplied. Summarize recurring exit reasons separately for product review.

Never contact an opted-out person, invent a reason, delete an account, issue a refund, exceed my offer cap, or promise unapproved work. Ask when the underlying churn list or required context is incomplete.

Prompt

Build a complete list of customers who cancelled or lapsed during the previous six months. Include name, email, former plan, cancellation date, and recorded reason when available.