← ALL PLAYBOOKS
PLAYBOOK · GTM STRATEGY
✓ APPROVED

Build a GTM plan you can defend

The annual plan is a wish. Build the number, the capacity, the territories, and the comp that make it real.

[ SALES OPERATOR ]

Build a GTM plan you can defend

G / Groundthe problem that started all of it
GTM Strategy

The annual plan is a wish.

Build the number, the capacity, the territories, and the comp that make it real.

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
Write a GTM plan you can actually defend.
Details
Structure the bets, motions, targets, and risks, with a first-pass directional capacity check on whether the number is reachable at all.
Powers up with
AI
Salesforce02
Know if the heads can hit the number, before the quarter.
Details
Take that directional check further: build the granular hiring plan, ramp curve, and attrition backfill the board plan needs.
Powers up with
AI
Salesforce03
Cut fair territories, settled before the disputes start.
Details
Cut fair, balanced patches before the disputes start.
Powers up with
AI
Salesforce04
Design comp and quota a rep trusts and a CFO signs.
Details
Design comp and quota a rep trusts and a CFO signs.
Powers up with
AI
T / Tie backthe result it drove, and how they know
RESULT · 01

The gap to target closed with a plan, not a wish

Capacity math, territories, and comp modeled before a single hire, on the same GTM turnaround.

OUTPUT · 01

A verdict-first plan: the bets

OUTPUT · 02

The capacity math

OUTPUT · 03

Fair territories

OUTPUT · 04

Comp that drives the right behavior

The Sales Operator
01 / WHY RUN IT

The annual plan gets built as a hope. Someone picks a number that sounds ambitious, sales agrees to it in the room, and nobody actually checks whether current headcount, territories, or comp can produce it, so the miss shows up in Q2 and the plan gets rewritten anyway.

RUN THIS AND YOU CAN
A verdict-first plan built on named bets, not a wish
The hiring gap sized in heads and dollars before you ask for budget
Territories cut fair enough that disputes get settled before kickoff
Comp and quota a rep trusts and a CFO signs
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
Write a GTM plan you can actually defend.

Verdict-first: the two or three bets, the motions, the targets, the capacity math, and the risks.

YOU GETThe verdict, the bets, the capacity math, and the risks.
OPEN THE SKILL →
2✓ TESTED
Know if the heads can hit the number, before the quarter.

Ramped-rep productivity, the hiring plan to close the gap, honest ramp assumptions, and the plan-vs-capacity gap.

YOU GETRamped productivity, the hiring plan, and the gap in dollars and heads.
OPEN THE SKILL →
3✓ TESTED
Cut fair territories, settled before the disputes start.

The segmentation, the account distribution, a balance check across every rep, and the rules for disputes and inbound.

YOU GETThe segmentation, the balance check, and dispute rules.
OPEN THE SKILL →
4✓ TESTED
Design comp and quota a rep trusts and a CFO signs.

The quota build (top-down vs bottom-up reconciled), the OTE mix, the accelerators, and the behaviors it drives and breaks.

YOU GETThe quota build, the OTE mix, the accelerators, and the behavior read.
OPEN THE SKILL →
WHERE YOU LAND

A verdict-first plan: the bets, the capacity math, fair territories, and comp that drives the right behavior.

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 CRO has to defend next year's plan to the board: a $24M target with 8 ramped AEs and 4 planned hires.

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.

FINANCE
The revenue target and budget envelope the plan builds to

Without it: The plan and the board deck tell different numbers.

REVOPS
Historical conversion, ramp, and attrition data for the capacity model

Without it: The capacity math runs on optimism.

MARKETING
The pipeline commitment behind the sourced-mix assumption

Without it: The model staffs reps for pipeline nobody is building.

SALES LEADERSHIP
Manager buy-in on territories and quota before rollout

Without it: The plan launches and the appeals start day one.

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 CHATRay, CRO, running the loop in one sitting
R
Board wants next year's plan. Right now it is a number I made up. Help me build one I can defend.
S
Step 1· Gtm Planning
Verdict: REACHABLE_IF. I framed the two or three bets, the motions behind each, the targets, and the risks up front, so the plan reads as a set of decisions instead of a spreadsheet.
Receipt
Plan on 2 bets: expand mid-market outbound and land a partner channel, each with a target and named risk.
R
Can the team we have actually produce that number?
S
Step 2· Capacity Model
I ran ramped-rep productivity against the target with honest ramp assumptions. There is a gap, and I sized it in both dollars and heads so the hiring ask is grounded.
Receipt
Current heads cover $18M of a $24M target, a $6M gap that needs 4 more ramped AEs.
R
Okay, now cut the territories so the reps stop fighting about it.
S
Step 3· Territory Design
I segmented the accounts and distributed them into balanced patches, then ran a fairness check across every rep. I also wrote the rules for disputes and inbound so it is settled before kickoff.
Receipt
9 patches within 8% of each other on account value, with tie-break rules written.
R
Last piece. Comp and quota the reps will trust and finance will sign.
S
Step 4· Comp Quota Plan
I reconciled a top-down and bottom-up quota, set the OTE mix and accelerators, and called out the behaviors the plan drives and the ones it quietly breaks. No surprises in Q3.
Receipt
Quota set at $1.1M per AE with a 2.6x pipeline coverage assumption and accelerators past 100%.
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 · AI-NATIVE GTM
A mid-stage B2B SaaS
2x
win rate. Twice as many of the same conversations became deals
$1M+
product-led pipeline in 6 months, a channel built from zero
1.5x
average deal size. Half again bigger, same seller
~2x
new-business revenue, on a far leaner engine
WHAT I DID
01
Owned the full commercial number. New business, retention, and expansion across SDR, Sales, and Customer Success, unified so what a rep learns in the deal reaches the CSM and expansion compounds instead of leaking.
02
Made retention proactive. An expansion and churn-risk model that flags accounts before they slip. Churn stopped and the installed base grew, cohort by cohort, on household-name accounts already on the product.
03
Rebuilt the ICP on who actually buys. More than a thousand customer and prospect calls, pressure-tested against won and lost deals. Reps stopped chasing good-looking accounts that never close, and deal sizes and win rates both climbed.

Rebuilt GTM for the AI era, from headcount to workflows.

See the full story
06 / ROLL IT OUT AND INSPECT IT · THE OTHER HALF

The plan is only as good as the math underneath it

The four skills hand you the bets, the capacity model, the territories, and the comp design; the plan survives contact because the people carrying the number believe the math. Here is how a GTM leader turns a planning doc into a number the front line signs up for instead of one handed down.

THE FRAMEWORK BEHIND IT
The red-team readout

Before the plan locks, a rep, a manager, and a finance partner each get an hour to attack it: the ramp assumptions, the territory cuts, the comp math. Every objection gets an answer in the doc or a change to the plan.

  1. 01
    Teach managers the capacity math

    Walk every front-line manager through the capacity-model assumptions: ramp time, attrition, quota coverage. A manager who can rebuild the math can defend the number to a rep.

  2. 02
    Pressure-test territories before they publish

    Run the territory-design cuts past the reps who will carry them while they are still drafts. Fairness argued in private beats disputes litigated all year.

  3. 03
    Model comp against real behavior

    Take last year's actual deals and run them through the comp-quota-plan design. If the plan pays wrong on deals you already know, it pays wrong next year too.

  4. 04
    Reforecast the plan quarterly

    The plan is a living model, not an annual ceremony. Each quarter, rerun the capacity math against actual hiring and attrition, and adjust the bets in gtm-planning before the gap compounds.

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 Build a GTM plan you can defend step by step, and run each skill as we go.
GET THE NEXT PLAYBOOK

One runnable workflow a week. Free.