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PLAYBOOK · CUSTOMER SUCCESS
✓ APPROVED

Get a new customer to value, and keep them

They signed, and the CSM inherits a cold handoff, guessing at what success even means for two weeks. Get them to value fast so the renewal is already won.

[ SALES OPERATOR ]

Get a new customer to value, and keep them

G / Groundthe problem that started all of it
CS

They signed, and the CSM inherits a cold handoff, guessing at what success even means for two weeks.

Get them to value fast so the renewal is already won.

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
Build the plan that predicts the renewal a year out.
Details
Turn their goals into time-to-value milestones.
Powers up with
AI
Amplitude02
Fix 'they bought it but nobody uses it.'
Details
Build the one habit that drives stickiness.
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AI
Amplitude03
Know if a new customer will stick, by day 90.
Details
Track Day 30/60/90 activation.
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AI
Salesforce04
Turn account data into a QBR that earns the renewal.
Details
Turn the data into a renewal-earning review.
Powers up with
AI
T / Tie backthe result it drove, and how they know
RESULT · 01

The first 90 days, scored

An early-warning motion built to start the day they sign, so a stalled time-to-value gets caught, not guessed at.

OUTPUT · 01

A goal-tied plan

OUTPUT · 02

An adoption habit

OUTPUT · 03

A first-90-day read

OUTPUT · 04

A QBR that earns the renewal

The Sales Operator
01 / WHY RUN IT
RUN THIS AND YOU CAN
A goal-tied plan
An adoption habit
A first-90-day read
A QBR that earns the renewal
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
Build the plan that predicts the renewal a year out.

Translates the customer's goals into measurable outcomes, time-to-value milestones, and the leading indicators that flag risk early.

YOU GETThe goal translation, the milestone sequence, and the leading-indicator set.
OPEN THE SKILL →
2✓ TESTED
Fix 'they bought it but nobody uses it.'

Reads what's unused, picks the one habit to build next, and writes the enablement plan that gets there.

YOU GETThe adoption gap, the next habit, and the enablement plan.
OPEN THE SKILL →
3✓ TESTED
Know if a new customer will stick, by day 90.

Tracks Day 30 / 60 / 90 activation, scores the sales-to-success handoff, and catches accounts a fit score wrote off while they were adopting.

YOU GETThe 30/60/90 milestone framework, the handoff scorer, and the time-to-value read.
OPEN THE SKILL →
4✓ TESTED
Turn account data into a QBR that earns the renewal.

Value delivered, adoption vs stated goals, risks named first, the roadmap, and one outcome-tied expansion ask.

YOU GETThe value story, the adoption read, the roadmap, and a slide-by-slide outline.
OPEN THE SKILL →
WHERE YOU LAND

A goal-tied plan, an adoption habit, a first-90-day read, and a QBR that earns the renewal.

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: A 50-seat mid-market deal just closed and the CSM inherits the account with only the sales-to-CS handoff notes, no defined success criteria.

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.

SALES LEADERSHIP
A handoff standard: goals, promises, and stakeholders in writing

Without it: The CSM spends two weeks re-discovering what sales already knew

PRODUCT
Activation data and fixes for the friction onboarding surfaces

Without it: The same snag stalls every new customer, forever

REVOPS
Instrumentation behind the Day 30/60/90 activation read

Without it: Onboarding health is a feeling, not a number

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 CHATRiley, a CSM, running the loop in one sitting
R
New logo just closed and it's handed to me. How do I set up a plan that actually predicts the renewal?
S
Step 1· Success Plan
Translated their stated goals into measurable outcomes, sequenced the time-to-value milestones, and named the leading indicators that flag risk early. Their goal was faster rep ramp, so we set a first-value milestone at day 21.
Receipt
Success plan tied to their goal: first value by day 21, renewal-predicting indicators set.
R
They bought 50 seats but I want to make sure people actually use it. What's the adoption plan?
S
Step 2· Adoption Plan
Read what's likely to go unused, picked the one habit to build first, daily sequence sends, and wrote the enablement plan to get there. Building one habit beats pushing every feature at once.
Receipt
Adoption plan targets one core habit for week 1, enablement steps mapped for all 50 seats.
R
We're 60 days in. Are they actually on track, or is a fit score fooling me?
S
Step 3· Onboarding Analyst
Checked Day 30 / 60 / 90 activation, scored the sales-to-success handoff, and caught that this account looked weak on paper but is quietly adopting ahead of pace. Time-to-value is beating the plan.
day 60on track
handoffclean
Receipt
Day 60 read: activation ahead of plan, account a false-negative on the fit score.
R
First quarterly review is coming up. Build the QBR.
S
Step 4· Qbr Builder
Pulled the value delivered, adoption against their stated goals, named the one risk up front, laid out the roadmap, and set one outcome-tied expansion ask. Built it slide by slide so it earns the renewal.
Receipt
QBR ready, value story plus one expansion ask, account tracking to a clean renewal by day 90.
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

The handoff is only as good as the first goal written

The skills hand a CSM a goal-tied plan, an adoption habit, an activation read, and a QBR; the renewal is decided in the first weeks, when the customer learns whether anyone heard what they bought this for. Here is how a CS leader makes the first goal conversation a standard, not a talent.

THE FRAMEWORK BEHIND IT
The day-one goal standard

Every new account opens with the success-plan goal conversation inside the first week, and CSMs certify on running that conversation before they take kickoffs solo. Inspect the written goal, not the kickoff deck.

  1. 01
    Teach the goal translation

    Train CSMs to turn a stated business goal into time-to-value milestones instead of a feature checklist. The success-plan is only as useful as that translation.

  2. 02
    Make Day 30 a tripwire

    The onboarding-analyst read at Day 30 either confirms the plan or changes it. A miss triggers a revised plan and a customer conversation, not a note in the CRM.

  3. 03
    Rehearse the habit pitch

    The adoption-plan bets on one habit. Roleplay the moment the CSM sells that habit to a busy team that did not choose the tool.

  4. 04
    Read QBRs against the first goal

    Before any qbr-builder deck ships, check it against the original success plan. If it cannot name progress toward the goal the customer stated, it is not ready for the room.

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 Get a new customer to value, and keep them step by step, and run each skill as we go.
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