When to send, and when to hold
Win-back is for people you already had: trial expired, cancelled, or the account closed after a quiet stretch. Never-activated accounts belong on onboarding. Quiet users who still have an open account belong on the lifecycle email hub. A coupon to everyone silent for 60 days is a different job.
- Trial expired, and they used the product at least once.
- Cancelled, and they are actually gone (not a same-night save offer).
- Never came back after a quiet stretch closed the account.
Hold if you emailed them last week, an automation already covers the moment, you have nothing specific to say, or complaint rates are climbing. Ramp.
How to write it
Give one reason: the workspace is still there, something they used shipped, or the last thing they did has a next step. Do not open with “we miss you” or a percent off.
| Use | Throw out |
|---|---|
| your Northwind workspace is still here | we miss you |
| Shared boards shipped the thing you were waiting on | come back and save 10% |
| trial ended: 3 projects are still in Northwind | it's been a while |
| we'll stop after this | special offer inside |
| Maya, nothing to re-create | your account misses you |
Examples
Hey Maya,
Trial ended last Friday. 3 projects are still in Northwind. Nothing was deleted.
Pick up here: https://app.acme.com/continue
Alex
Why it works
The work is still there. No coupon.
Hey Maya,
When you cancelled March 2, you were using Shared boards. That gap shipped this Monday.
If that was the blocker: https://app.acme.com/continue
Alex
Why it works
The reason to return is a shipped gap, not 10% off.
Hey Maya,
Northwind is still here, including the board you last edited on Tuesday evening. Nothing to rebuild.
https://app.acme.com/continue
Alex
Why it works
Nothing to re-create is a better reason than “we miss you.”
Hey Maya,
We'll stop after this. If you want the workspace back: https://app.acme.com/continue
Otherwise I will not keep writing.
Alex
Why it works
Stopping protects the list. A six-email sunset series would not.
What to measure
Return or paid conversion against a holdout. Opens do not count.