── SKILL
winback-play✓ APPROVED

Win a churned customer back by re-onboarding, not discounting.

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.

In plain English: “Which lost customers can we actually win back?

Inside: The winnable test, the real-reason read, the change-signal timing, and the re-onboarding sequence.

01 / HOW TO USE

Install it in one line, or paste it in.

1
In Claude Code (one command)
Copy the install line, paste it into your terminal, and restart Claude Code. The skill installs itself to ~/.claude/skills/ and runs automatically when it is relevant.
2
In Claude, ChatGPT, or a Project (no terminal)
Open the file, then upload it to your chat or paste its contents in. A skill is just a markdown file of instructions, so any capable AI can follow it.
New to skills? A skill is a plain-text file that teaches your AI a workflow. Point any capable assistant at it and it follows the steps, on your data.
02 / MAKE IT YOURS

Connect your context. Set it to your motion.

CONNECT YOUR CONTEXT · AND WHY IT HELPS
a CRM

it reads the full history, the champion, the original value, and whether the door was left open.

a product-analytics tool

it sees if they spun up a competitor or if the gap that made them leave still exists.

a signal source

it catches the change that reopens the door, a new leader, a fresh round, a reorg.

SET IT TO YOUR MOTION

This was built to be motion-agnostic. Set these to your win-back:

The play is yours. The point is to re-onboard a returning customer, not to blast a discount at everyone who ever left.

Set thisWhat it isDefault / Example
WINDOWhow long after churn you reach back90 daysretune to your cycle
WINNABLE_TESTwhat makes an account worth chasingthe reason they left has changed
CHANGE_SIGNALSwhat reopens a doornew leadernew roundreorgcompetitor pain
RE_ONBOARDhow you welcome them backthe same care as first timewarm not salesy
CHANNELSwhere the reach-back runsthe champion's inboxa human note
VOICEthe tone of the returnglad you're backnot "we miss your money"
03 / THE FULL SKILL

Everything the skill does, in full.

── WHAT THIS DOES

Builds the play to win a churned customer back, and treats the return like an onboarding, not a discount. It reads why each account left, whether the exit left a door open, and whether anything has changed on their side, then picks the ones actually worth chasing and writes a warm re-onboarding sequence for each. The premise: a returning customer should feel the same care they felt the first time, because the reason they come back is rarely the price, it is the feeling that they were wanted. Boomerang customers are real revenue, and this is the motion that earns them.

── THE METHOD
  1. 1
    Pick the winnable, drop the gone

    Not every churned account is worth chasing. Sort them: winnable means the reason they left has changed or was never really about your product. Gone means the gap that pushed them out still exists. Chasing the gone burns goodwill and your time. Name which is which before you write a word.

  2. 2
    Read why they actually left

    The stated reason and the real reason differ. Price is usually a proxy for value not felt. Missing feature is often onboarding that never showed them the feature. Read the real reason, because the win-back has to answer it, not the surface complaint.

  3. 3
    Wait for the door to reopen

    A win-back lands when something changed: a new leader with a new mandate, a fresh round and new pressure, a reorg, or the competitor they left for disappointing them. Time the reach-back to the change, not to a calendar. A cold "we miss you" with nothing new is why win-backs get ignored.

  4. 4
    Re-onboard, do not re-sell

    The reach-back is a welcome, not a pitch. Lead with what changed on your side that answers why they left, offer to make the return effortless (their config kept warm, their data ready), and bring back the human who knew them. The feeling is glad you are back, not glad to have your money again.

  5. 5
    Build the sequence

    Write the actual touches: the warm opener tied to the change, the make-it-easy offer, the human re-onboarding. Short, specific, and human. If the sequence could be sent to anyone who ever churned, it is a discount blast, not a win-back. Rewrite until the account's real reason is load-bearing.

── QUALITY GATES
  • Every account is sorted winnable or gone, with the reason. No blanket chase of the whole churn list.
  • The real reason they left is named, not just the stated one.
  • The reach-back is timed to a change signal, never a generic "we miss you."
  • The sequence re-onboards, it does not re-sell. No desperation discount as the opener.
  • The message fails if it could be sent to any churned account. Rewrite until the reason is load-bearing.
── OUTPUT (EXAMPLE)
EXAMPLE OUTPUT
WIN-BACK PLAY · Northwind (illustrative) · churned 7 months ago

Winnable?   YES. Left for a competitor over a missing integration.
            That integration shipped in Q1. The reason is gone.
Real reason Not price. They were never fully onboarded onto the
            workflow that would have made the integration matter.
Door open?  Yes. New VP started 6 weeks ago (change signal).
            Original champion still there.

RE-ONBOARDING SEQUENCE:
  Touch 1 (to the champion): "The integration you needed shipped.
    Thought of you. No pitch, just wanted you to know."
  Touch 2 (to the new VP): a warm intro via the champion, framed as
    "worth another look given what changed."
  Touch 3 (the return): "We kept your config warm. If you want back
    in, it's a 10-minute restart, not a rebuild."

Not sent: any "we miss you, here's 30% off." That answers nothing.
── EXAMPLE CHAT
EXAMPLE CHAT
You
We lost Northwind 7 months ago. They said we were too expensive and went with a cheaper tool. Should we chase them?
CLAUDE
Depends whether the real reason changed, and price is almost never the real reason. Let me read it: if they left purely on cost and nothing has changed, they are gone, do not burn the goodwill. But "too expensive" usually means "I did not feel enough value to justify it," which is an onboarding problem wearing a pricing costume. Was Northwind ever fully onboarded onto your core workflow?
You
Honestly no. They set up the basics and never got to the automation piece.
CLAUDE
Then this is winnable, and the win-back is not a discount, it is the onboarding they never got. Here is the play: Touch 1: warm note from their old CSM, not sales. "Been thinking about your team. When you were with us, you never got to the automation piece, which is the part that would've paid for the whole thing. Can I show you in 15 minutes, no strings?" Touch 2: if they bite, re-onboard for real, start at the value they missed, not at setup. Touch 3: make the return effortless, keep their old config warm. The reason is load-bearing: this message only makes sense for an account that churned under-onboarded. One sharpener: connect a signal source and I will time the reach-back to a real change on their side, a new leader or a fresh round, so you knock when the door is actually open.
04 / GO FURTHER

Where an operator takes this next.

The play is step one. Here is where an operator takes it once it works.

You stop treating churn as final and start treating it as a list.

01
Run the boomerang list on a schedule

Have a Claude task sweep churned accounts monthly, sort winnable versus gone, and surface only the ones whose door just reopened to the CSM in Slack.

02
Wire change signals to the reach-back

Connect a signal source so a new leader or a fresh round at a churned account triggers the win-back play automatically, timed to the change instead of a calendar.

03
Close the loop to onboarding

Feed every win-back reason back into the onboarding audit, because the same gap that lost them is the one costing you the next cohort.

05 / PART OF A BIGGER PLAY

One skill is the on-ramp.

── GET NEW SKILLS IN YOUR INBOX

One operator-built skill a week. Free.