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PLAYBOOK · SALES ENABLEMENT
✓ APPROVED

Turn any build or framework into rep-ready enablement

You shipped the system, or rolled out the framework, and adoption is uneven. Most enablement is a deck and a kickoff that evaporates. Turn it into a module reps can practice and be certified on.

[ SALES OPERATOR ]

Turn any build or framework into rep-ready enablement

G / Groundthe problem that started all of it
Sales Enablement

You shipped the system, or rolled out the framework, and adoption is uneven.

Most enablement is a deck and a kickoff that evaporates. Turn it into a module reps can practice and be certified on.

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.
Anchor it
Claude01
Turn a category into a real ICP definition.
Details
Anchor the enablement in the account tier this build applies to, then name the individual buyer inside it, a person, a day, a problem, as the PERSONA the next step needs.
Connect to analyze
AI
Build the module
Claude02
Walk in with the questions that qualify.
Details
Take the persona you just named as its PERSONA input, and build the questions for this motion, mapped to your framework.
Connect to analyze
AI
Salesforce03
Build a demo that maps to the buyer's problems.
Details
Write the talk track that maps to stated problems, and cut what does not map.
Powers up with
AI + human
Practice it
Gong04
Practice the call before the call.
Details
Generate the AI roleplay so reps practice and get certified before the live call.
Powers up with
AI + human
Ramp it
Claude05
Turn a start date into a ramp that ends in quota.
Details
Wrap it into a 30/60/90 ramp with a certification bar and manager touchpoints.
Connect to analyze
AI
T / Tie backthe result it drove, and how they know
RESULT · 01

The other half of the deal hub

The system cut the busywork; the deal review and the coaching are what moved the deal.

RESULT · 02

Coached reps to earn the room

The love test found the gap; rehearsing the reach-up is what closed it.

RESULT · 03

Rehearsed the save before the call

The score saw the churn coming; the renewal review and the roleplay did something about it.

OUTPUT · 01

An account tier

OUTPUT · 02

The buyer persona inside it

OUTPUT · 03

The questions

OUTPUT · 04

The talk track

The Sales Operator
01 / WHY RUN IT
RUN THIS AND YOU CAN
An account tier
The buyer persona inside it
The questions
The talk track
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.

1Anchor it✓ TESTED
Turn a category into a real ICP definition.

Names your tiers with explicit criteria, the fit signals, the anti-ICP you exclude on purpose, and a qualification framework, plus an evolution log. A category is not a definition.

YOU GETThe tier criteria, the anti-ICP, the must-have vs red-flag framework, and the evolution log.
OPEN THE SKILL →
2Build the module✓ TESTED
Walk in with the questions that qualify.

Tailored discovery questions sequenced problem to impact to next step, each mapped to your qualification framework.

YOU GETThe question set, the impact quantifiers, and the field each question maps to.
OPEN THE SKILL →
3Build the module✓ TESTED
Build a demo that maps to the buyer's problems.

Maps every feature you plan to show to a problem the buyer actually stated, and cuts what does not map.

YOU GETThe problem-to-moment map, the 'so what' per beat, and the cut list.
OPEN THE SKILL →
4Practice it✓ TESTED
Practice the call before the call.

Turns a deal, framework, or objection into a live AI roleplay partner, then scores the rep against the framework with a cert bar.

YOU GETThe buyer persona, the real objections, and a framework-scored, pass-or-not-yet scorecard.
OPEN THE SKILL →
5Ramp it✓ TESTED
Turn a start date into a ramp that ends in quota.

A 30/60/90 with milestones, a certification bar before full load, and the manager touchpoints that catch a slow ramp early.

YOU GETThe 30/60/90 gates, the certification bar, and the manager touchpoints.
OPEN THE SKILL →
WHERE YOU LAND

An account tier and the buyer persona inside it, the questions, the talk track, an AI roleplay to practice against, and a 30/60/90 ramp with a certification bar. The people half of every build, made runnable.

EVERY STEP, TESTED AND PASSED
EVAL RESULTPASS4/4 dimensions
HOW WE EVAL →
Skills resolve
Structure + proof
Example chat
Quality judge
  • All 5 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 Head of Sales rolled out the product-channel play last month; adoption is inconsistent because half the team never got real enablement on it, just a Slack announcement.

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
Manager time for cert reviews and ramp touchpoints

Without it: The module evaporates like the deck it replaced.

PRODUCT
Accuracy of the demo script and capability claims

Without it: Certified reps demo things the product cannot do.

MARKETING
The persona research and positioning under the module

Without it: Reps drill the wrong buyer, fluently.

REVOPS
Ramp and adoption metrics tied to cert dates

Without it: Nobody can show the module moved the 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 CHATRenata, Head of Sales, running the loop in one sitting
R
We rolled out the product-channel play and adoption is all over the place. Half my reps do not know how to work a product lead. Enable the team on it, properly, not another slide deck.
A
Anchor· Define your ICP
Enablement built on a feature list teaches reps to talk about you. So we start with the account: which tier this motion applies to, then name the buyer inside it, the day they are having, and the problem the usage points to.
Receipt
Tier 1 fit: an ops-led team already on the free tier. The buyer inside it, one line: an ops lead using it weekly, hitting the wall on a paid feature, with no time for a migration.
B
Build· Discovery question builder
Now the questions for this motion, mapped to SPRINT, plus the talk track that opens with what they are already doing in the product, not a pitch.
Receipt
A rep one-pager: 6 discovery questions, the usage-first opener, and the two objections a product lead actually raises.
P
Practice· Roleplay scenario generator
Then reps rehearse it against a live roleplay before the real call, and I score them on the framework so ready is a decision, not a hope.
Receipt
A roleplay per rep plus a cert bar. Two reps passed, three are a not-yet with the one gap named.
R
Ramp· Enablement plan
Last, I wrap it into a 30/60/90 with a certification gate and your manager touchpoints, so a slow ramp shows up in week three, not month three.
Receipt · the module, shipped
One module: buyer, questions, talk track, roleplay, and ramp. Every rep certified on the product-channel play before they touch a live PQL.
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 · DEAL VELOCITY
The Deal Hub
>25%
shorter sales cycle, the late stage streamlined
Sub-45 days
SMB and Mid-Market, end to end
Sub-90 days
Enterprise, end to end
12 tabs → 1
the late-stage deal moved out of browser tabs into one hub, and discounts fell with the friction
WHAT I DID
01
One home for the deal. A hub where the proposal, the plan, and the next step lived together, so nothing had to be assembled from twelve tabs before a conversation.
02
The customer sees what is next. Instead of waiting on a forwarded email, the customer could see what happened next, which removed a whole class of stall.
03
Map the handoffs, then close each gap. I walked the late stage handoff by handoff, quote to security review to mutual plan to approval, found where each one sat waiting, and put the next step and its owner in the hub so no stage stalled on someone's inbox.

Speed in a deal is not pressure. It is removing the places a deal goes to wait. Find where your deals stall, then remove the wait, not the patience.

Dig into the full build
THE BUILD · LENS: DEAL EFFORT
The Love Test
~2
touchpoints per account, on average, my reps
5%
win rate when a deal is single-threaded
40%
of deals die from single-thread dependency
6.8
stakeholders in the average B2B purchase
WHAT I DID
01
The love test. I ran the analysis: were reps earning attention through multi-step prospecting, or just reacting to whoever already showed it? The data was blunt. Reps averaged about two touchpoints per account and over-indexed on inbound, neglecting every other channel. Effort was following responsiveness, not opportunity.
02
Make persistence a motion, not a mood. If most deals need five or more touches and reps average two, the fix is not motivation. It is a multi-step prospecting motion that runs across every channel, whether or not the account has written back yet.
03
Thread the deal, not the champion. Ladder each altitude of the problem, personal, team, and org, to the person who owns it, so the deal survives any one contact going dark. Multi-threading covers the whole buying committee, not just the contact who answers first.

Reps invest effort where interest already exists. The fix is not more leads, it is a prospecting motion that earns attention before the account gives it: multi-step, every channel, threaded across the whole buying committee.

Dig into the full build
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 module is only as good as the manager inspecting it

The skills hand the team a persona-anchored module: the questions, the talk track, the roleplay, and the ramp; the adoption comes from managers holding the bar after the kickoff ends. Here is how an enablement leader makes the module stick past week two.

THE FRAMEWORK BEHIND IT
The certify-then-verify cycle

Every rep clears the roleplay cert bar before running the motion live, then a manager listens to a real call within two weeks to verify the module survived contact. Gaps go back into the module, not into a reminder email.

  1. 01
    Anchor every rep in the persona

    Before the questions or the talk track, have each rep describe the persona from define-your-icp in their own words: the person, the day, the problem. A rep who cannot say it will not discover it.

  2. 02
    Run the cert bar for real

    The roleplay-scenario-generator sets the scenario; the bar is pass or not yet, with a scheduled retry. A cert everyone passes on attempt one is a ceremony, not a bar.

  3. 03
    Keep manager touchpoints on the calendar

    The 30/60/90 in the enablement-plan names manager checkpoints; hold them as standing meetings, not intentions. The ramp slips exactly where the touchpoints do.

  4. 04
    Verify on live calls, then revise

    Listen to real calls against the demo-script and question set, and treat every recurring gap as a module defect first. Fix the module before coaching the rep on it twice.

07 / INSTALL THE WHOLE PLAYBOOK

One plugin. 5 skills, bundled.

The whole playbook installs as a single plugin in Claude Code, no copy-pasting 5 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 Turn any build or framework into rep-ready enablement step by step, and run each skill as we go.
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