← ALL PLAYBOOKS
── PLAYBOOK · CUSTOMER SUCCESS
✓ 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.

[ BUILT GTM ]

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

Solvethe problem worth solving
Problem · 01CS

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.

Stackthe workflow, box by box
Salesforce01
Turn churn themes into an early-warning system.
Extract why accounts actually left, not the stated reason.
Powers up with
AI
Salesforce02
Win a churned customer back by re-onboarding, not discounting.
Match the levers to the real cause, then re-onboard instead of discounting.
Powers up with
AI
Amplitude03
Turn a buying signal into a timely touch.
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.
Powers up with
AI
Outreach04
Turn one signal into a cold email that earns a reply.
Write the win-back touch itself, on one idea, using the angle and timing trigger-outreach just flagged.
Powers up with
AI
Splithow control passes: agents branch left, humans right
HUMAN + AI, IN THE LOOP
How control passes.
AgentsHuman
Agent01
Turn churn themes into an early-warning system.
Salesforce runs it.
Agent02
Win a churned customer back by re-onboarding, not discounting.
Salesforce runs it.
Agent03
Turn a buying signal into a timely touch.
Amplitude runs it.
Agent04
Turn one signal into a cold email that earns a reply.
Outreach runs it.
The skills run the work. You stay in the loop on the calls that need judgment.
Outputwhat the workflow produces
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

Outcomethe result it drives
OUTCOME · 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.

Built GTM
── 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 2026-08-05
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 / 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.
── 04 / 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
05 / 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.
── GET THE NEXT PLAYBOOK

One runnable workflow a week. Free.