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✓ APPROVED

Diagnose the churn, then re-open on a real trigger

The accounts you lost are the warmest pipeline you are ignoring. This is the outbound play: diagnose the real reason from usage and support data, then re-open with a timed, relevant trigger, not an onboarding audit and not a we-miss-you blast.

[ SALES OPERATOR ]

Diagnose the churn, then re-open on a real trigger

G / Groundthe problem that started all of it
CS

The accounts you lost are the warmest pipeline you are ignoring.

This is the outbound play: diagnose the real reason from usage and support data, then re-open with a timed, relevant trigger, not an onboarding audit and not a we-miss-you blast.

A / Assignthe build, block by block, and who owns each one. Open a step to see it run.
HUMAN + AI, IN THE LOOP
The skills run the work. You stay in the loop on the calls that need judgment.
Salesforce01
Turn churn themes into an early-warning system.
Details
Extract why accounts actually left, not the stated reason.
Powers up with
AI
Salesforce02
Win a churned customer back by re-onboarding, not discounting.
Details
Match the levers to the real cause, then re-onboard instead of discounting.
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AI
Amplitude03
Turn a buying signal into a timely touch.
Details
Catch the fresh signal and confirm it is inside the freshness window; hand the angle and timing to cold-email-writer instead of drafting the touch here.
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AI
Outreach04
Turn one signal into a cold email that earns a reply.
Details
Write the win-back touch itself, on one idea, using the angle and timing trigger-outreach just flagged.
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AI
T / Tie backthe result it drove, and how they know
RESULT · 01

Churn and downgrades down 28%

The churn side of that system: the same signals that catch risk early also single out which already-lost accounts are worth a re-open.

OUTPUT · 01

The real churn theme

OUTPUT · 02

A win-back angle matched to the cause

OUTPUT · 03

A timely

OUTPUT · 04

Relevant re-open on the accounts worth it

The Sales Operator
01 / WHY RUN IT
RUN THIS AND YOU CAN
The real churn theme
A win-back angle matched to the cause
Relevant re-open on the accounts worth it
02 / THE RUN, STEP BY STEP

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.

1✓ TESTED
Turn churn themes into an early-warning system.

Reads churned and downgraded accounts, extracts the themes, and flags active accounts that resemble recent churners.

YOU GETThe theme extraction, the early-warning checklist, and a predictive read on the active book.
OPEN THE SKILL →
2✓ TESTED
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.

YOU GETThe winnable test, the real-reason read, the change-signal timing, and the re-onboarding sequence.
OPEN THE SKILL →
3✓ TESTED
Turn a buying signal into a timely touch.

Read the trigger (funding, hire, launch, job posting, tech change), pick the one angle it earns, and write the touch while it is still fresh.

YOU GETThe trigger read, the freshness gate, and a one-angle draft.
OPEN THE SKILL →
4✓ TESTED
Turn one signal into a cold email that earns a reply.

From a prospect and a specific angle, writes a short email or 3-touch sequence built on one idea, no filler.

YOU GETThe one-idea rule, an earned opener, a soft CTA, and a 3-touch sequence.
OPEN THE SKILL →
WHERE YOU LAND

The real churn theme, a win-back angle matched to the cause, and a timely, relevant re-open on the accounts worth it.

EVERY STEP, TESTED AND PASSED
EVAL RESULTPASS4/4 dimensions
HOW WE EVAL →
Skills resolve
Structure + proof
Example chat
Quality judge
  • 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.
Last eval run 2026-09-12
DEEP EVAL · PASS
THE STANDARD →

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: Dani, CS Lead, lost 18 accounts and doesn't trust the exit-survey reasons.

03 / WHO ELSE HAS TO MOVE

This play runs across the org, not inside sales.

Every function below owns a piece of the play. Skip one and it stalls where most GTM plays stall: in the handoff.

PRODUCT
The shipped fixes behind every what-changed claim

Without it: The what-changed line is a hope, not a fact.

SALES LEADERSHIP
Rep time and credit for working the boomerang list

Without it: Win-backs lose to new logos on every calendar.

MARKETING
Suppression of churned accounts from generic nurture

Without it: A we-miss-you blast lands the week before your re-open.

FINANCE
Pricing guardrails for return offers

Without it: Every win-back becomes a discount, and it sticks.

04 / SEE IT RUN

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.

EXAMPLE CHATDani, Customer Success Lead, running the loop in one sitting
D
We lost 18 accounts over the last two quarters. Exit surveys all say price, but I don't buy that. Can you dig into what actually happened?
S
Step 1· Churn Analysis
I read the 18 churned accounts against their usage and support history, not just the exit note. Price was the stated reason on most, but the real pattern is a champion leaving and adoption never recovering. I also ranked the 18 by how closely each matches that theme, so you know which to prioritize.
churned18
real causechampion loss
Receipt
Real churn theme: 11 of 18 lost accounts show a champion departure and adoption drop 90 days before cancel, not price.
D
That changes everything. There's one account, a 40-seat customer, that fits that pattern exactly and left 4 months ago. How would I try to win them back?
S
Step 2· Winback Play
Since the real cause was losing their champion, a discount won't fix it. I matched levers to that: a re-onboarding offer for the new admin, a quick-win use case to rebuild value, and a check-in cadence, framed as a welcome back, not a re-sell.
Receipt
Win-back play built on champion loss: re-onboarding plus a 2-week quick-win, timed to the account's own change signal, not a calendar reminder.
D
I don't want to send a generic 'we miss you' email. Is there a reason to reach out to them right now specifically?
S
Step 3· Trigger Outreach
I checked for a fresh signal and found one: they just posted a job for an ops role that owns exactly the workflow we solve. That's the reason to reach out now, and it earns one specific angle instead of a check-in.
Receipt
Trigger found: a new ops hire req posted 6 days ago, giving a timely, relevant reason to re-open the account.
D
Perfect hook. Write me the actual email I'd send off that.
S
Step 4· Cold Email Writer
I wrote the win-back on one idea: the new role they're hiring owns the workflow that broke down after their champion left, and we can stand it up fast. Earned opener tied to the job post, no filler, soft CTA.
Receipt
Win-back email drafted on the hiring trigger, 89 words, one idea, ending in a low-friction ask for 15 minutes.
05 / SEE IT IN PRODUCTION

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.

THE BUILD · RETENTION + NRR
Proactive Retention
-28%
churn and downgrades, the year I took over
7 figures
churned-customer win-back the same read produced
66%
of renewals were getting zero renewal activity
69 to 180 days
first renewal touch, moved from late to early
WHAT I DID
01
Build the autopsies first. I ran churn, closed-won, and closed-lost analyses to learn what actually predicted a loss. Not opinions, patterns. You cannot build an early-warning system until you know what the early warnings are.
02
Give every CSM a book-of-business view. One place that showed every account, its health, its renewal date, its risk. Not a spreadsheet someone updated when they remembered.
03
Score the risk. Account-health churn-risk scoring that flagged the accounts turning cold while there was still time to do something. The signal, not the surprise.

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
06 / ROLL IT OUT AND INSPECT IT · THE OTHER HALF

A win-back is only as strong as the reason you bring

Churn-analysis and the winback-play hand the team the real reason accounts left and an angle matched to it; the return comes from a rep opening the right door at the right moment. Here is how a CS leader turns the boomerang list into booked re-opens instead of a we-miss-you campaign.

THE FRAMEWORK BEHIND IT
The reason-and-window drill

Every re-open gets stated in one sentence before it sends: the real reason they left, what changed, and why now. Reps rehearse that sentence out loud, and a touch with no fresh trigger inside the window does not go out.

  1. 01
    Teach the real-reason read

    Walk the team through how churn-analysis separates the stated reason from the actual one in usage and support data. A rep who leads with the stated reason reopens the old wound.

  2. 02
    Hold the freshness window

    Trigger-outreach flags the signal and the window; the SLA is that a fresh trigger gets its touch inside that window or the account goes back in the queue. Stale triggers are how win-backs read as blasts.

  3. 03
    Rehearse the what-changed line

    Roleplay the opening of the re-open: naming why they left without flinching, and what is different now. If the rep cannot say what changed, the play is not ready for that account.

  4. 04
    Inspect the re-opens by cause

    Review which churn themes and cold-email angles actually produced replies and meetings, then feed that back into the winback-play so the next pass works the causes that convert.

07 / INSTALL THE WHOLE PLAYBOOK

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.

OR KICK IT OFF IN CHAT
Here is my situation: [describe your workflow or account in a sentence or two]. Walk me through Diagnose the churn, then re-open on a real trigger step by step, and run each skill as we go.
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