Audit the welcome and the goodbye, find your boomerangs
You pour everything into onboarding and treat the exit as a cancel button. But a customer leaves feeling either trapped or respected, and only one of those ever comes back. This is not the outbound chase, it starts with your own experience: audit both ends, then build the boomerang.
Audit the welcome and the goodbye, find your boomerangs
You pour everything into onboarding and treat the exit as a cancel button.
But a customer leaves feeling either trapped or respected, and only one of those ever comes back. This is not the outbound chase, it starts with your own experience: audit both ends, then build the boomerang.
A scored onboarding experience
A scored exit
The churned accounts who were still getting value when they left
A warm re-onboarding sequence for each
Saw the churn before it happened
This is the retention-scoring half, not this exact audit: it caught at-risk accounts early. The boomerang play in this playbook is the other half, what you do once one has already left.
Scored who was worth keeping
An adjacent scoring build, not a direct receipt: the same read that ranks expansion candidates is the pattern this playbook's boomerang list extends to churned accounts.
You pour everything into onboarding and treat the exit as a cancel button. The welcome feels like a five-star hotel and the goodbye feels like a parking ticket, so the customer who might have come back leaves feeling trapped instead of respected. Then you blast a we-miss-you discount six months later and wonder why nobody answers.
The workflow that solves it, one step at a time.
Each step is the plain question you are already asking. The skills answer them in order, one handing its receipt to the next.
Grades the first 90 days on the moments that make someone feel expected, not just whether they activated, and names the exact spot the welcome goes cold.
Grades the exit most companies treat as a cancel button, finds where a leaving customer gets punished or ghosted, and shows how to leave the door open for a boomerang.
Turns raw usage into per-capability adoption tiers, a 12-week trend on each, power-user IDs, and a ghost-active flag.
Sorts churned accounts winnable versus gone, reads why they really left, times the reach-back to a change on their side, and writes a warm re-onboarding sequence.
A scored onboarding experience, a scored exit, the churned accounts who were still getting value when they left, and a warm re-onboarding sequence for each.
- All 4 chained skills resolve to real, scored skills.
- Has a problem, an outcome, 2+ steps, and proof from a real build.
- Ships an example chat showing the play run in Claude.
- Reads in plain operator voice, grounded in a real build.
We did not just check the structure. A judge read this play against the full text of every skill it chains (composition), then ran it on a real scenario end to end (simulated). It passed both. Test scenario: Priya, Head of CS: onboarding is good but churn still happens and win-backs never land.
Watch the skills answer in order.
Describe your situation in plain language. The right skill fires on its own and hands its receipt to the next.
Before you run it, I ran it for real.
This workflow is genericized from a real build. Here is the number it moved, and what I actually did.
WHAT I DID ›
If your CSMs find out about churn from the customer, you do not have a retention motion, you have a notification system. Build the autopsy, score the risk, and start the renewal conversation ninety days out.
Dig into the full build →WHAT I DID ›
Expansion is not re-selling your champion. It is finding the untapped team next door, and refusing to cross-sell off a beachhead that is already going dark. Score the whitespace, gate on the health of what you sold, and check the score against your CSMs gut, because the divergences are where the money is.
Dig into the full build →The play is only as good as the team running it
The audits hand you a score and a boomerang list, but the win-back lives or dies in the conversation, not the report. Here is how a CS or sales leader enables the team to actually run this, so the read turns into returns instead of a dashboard nobody acts on.
The skills give the team the read; enablement trains the moment. Reps rehearse the re-onboarding pitch and the exit-with-dignity conversation against a live roleplay, and clear a cert bar before they ever touch a real churned account.
- 01Teach the read, not just the tool
Walk the team through what an onboarding cold spot and a bridge-burned score actually mean, so they trust the audit before they act on it.
- 02Rehearse the hard moment
The win-back is a conversation, not a discount email. Run the roleplay generator on a churned-but-still-engaged account so reps practice the re-onboarding pitch and the honest goodbye before it is live.
- 03Certify before they run it
No rep works the boomerang list until they clear the roleplay cert bar. Ready is a decision, not a hope.
- 04Coach on the flips
Review who came back and who did not, then feed the pattern back into the onboarding audit so the next cohort never churns the same way.
One plugin. 4 skills, bundled.
The whole playbook installs as a single plugin in Claude Code, no copy-pasting 4 times. Or grab any single step above. It runs on what you paste; connect your stack to go live.