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proposal-strategist

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Updated 10-16 08:08

About this skill

Proposal Strategist

READINESS GATE: Do not build a proposal until the deal is qualified. Check before proceeding.

DATA RULE: Every claim must trace back to a confirmed discovery quote or verified proof point. Never invent metrics.

DATE RULE: Check currentDate. Output saved as YYYY-MM-DD-proposal-draft.md.

STEP 0 — Readiness Gate

Before building anything, confirm ALL of these are true:

Gate Requirement Status
MEDDPICC Score 20+ (active opportunity minimum) Confirmed / Not yet
Identified Pain Confirmed with at least 1 direct quote Confirmed / Not yet
Economic Buyer Named — who will approve or sign Confirmed / Not yet
Decision Criteria At least 2-3 criteria articulated by buyer Confirmed / Not yet

If any gate is not met — STOP. Tell the seller: "This deal isn't ready for a proposal yet. The gap is [missing element]. Run /discovery-prep to fill it before the next call."

STEP 1 — Load Deal Context

Read all available files:

  1. accounts/{account}/account-brief.md → full MEDDPICC status, EB, champion, decision criteria
  2. accounts/{account}/discovery/ → all call notes (pain quotes, metrics they mentioned, language they used)
  3. accounts/{account}/meetings/ → meeting briefs and summaries
  4. accounts/{account}/research/ → company overview, tech stack, competitive context
  5. .claude/skills/write-outreach/references/proof-points.md → verified proof points to match

Extract from the files:

  • 3-5 confirmed pains in the buyer's exact words (direct quotes)
  • Decision criteria as they stated them
  • Metrics they care about (their numbers, not yours)
  • Economic Buyer's name + role + what they care about
  • Competitors in the deal (if any)

STEP 2 — Define Win Themes

Build 3-5 win themes. Each theme is: [Buyer's confirmed pain] + [Your specific capability] + [Proof metric]

And each theme must map to at least one confirmed decision criterion.

Win Theme Buyer Pain (quote) Your Capability Proof Metric Decision Criterion
1 "[direct quote]" [specific feature/approach] [verified metric] [their criterion]
2 "[direct quote]" [specific feature/approach] [verified metric] [their criterion]
3 "[direct quote]" [specific feature/approach] [verified metric] [their criterion]

Rule: If you can't find a direct quote for a theme, that theme is not confirmed. Remove it.

STEP 3 — Build the Three-Act Narrative

Act I — Understanding Their Situation

Mirror their world back to them. Zero product mentions.

Structure:

  1. Where they are today (their current state — use their language from discovery)
  2. What's breaking (the specific pain — use their direct quotes)
  3. What they've tried (prior solutions that didn't work)
  4. The cost of continuing this way (implication — their numbers or close estimates)

Quality gate: Re-read Act I. If {{PRODUCT_NAME}} appears anywhere — remove it. Act I is 100% about them.

Act II — The Solution

Map capabilities to confirmed pains. One section per win theme.

Structure per win theme:

  1. Recap the pain (1 sentence — their words)
  2. The specific capability that addresses it (feature/approach in plain language)
  3. How it works (1-2 sentences — concrete, not vague)
  4. Proof (1 customer example that mirrors their situation — source URL or proof-points.md ref)

Quality gate: Every capability in Act II must map to a confirmed pain from Act I. No orphaned features.

Act III — The Transformed State

Show the specific, quantified future using their own metrics.

Structure:

  1. [Their metric] changes from [current state] to [future state] — because of [specific capability]
  2. What becomes possible that isn't possible today (use their future state language from discovery)
  3. Timeline to value — when do they start seeing results?

Quality gate: Act III must use THEIR metrics (from discovery) not generic industry benchmarks.

Executive Summary (1 page, 5 sentences)

Write exactly 5 sentences:

  1. Situation: "[Company] is dealing with [specific pain in their words]."
  2. Cost of nothing: "Left unaddressed, this means [implication — their words or verified estimate]."
  3. What we do: "{{PRODUCT_NAME}} [specific capability] so that [specific outcome]."
  4. Proof: "[Customer] solved a similar challenge and achieved [metric] in [timeframe]."
  5. Next step: "We recommend [specific next step] by [date] to [achieve their goal]."

Quality gate: Read the executive summary aloud. It must stand alone in 90 seconds and make sense to someone who wasn't on any discovery call.

STEP 4 — Save Proposal Draft

Save as: accounts/{account}/meetings/YYYY-MM-DD-proposal-draft.md

Proposal file structure:

# Proposal Draft — {Company}
Prepared: {date}
For: {Economic Buyer name + title}
Prepared by: {{SELLER_NAME}} / {{AE_NAME}}

---

## Executive Summary
[5-sentence structure from Step 3]

---

## Understanding Your Situation (Act I)
[Act I content]

---

## The Solution (Act II)

### Win Theme 1: [theme title]
[Content]

### Win Theme 2: [theme title]
[Content]

### Win Theme 3: [theme title]
[Content]

---

## What Changes (Act III)
[Act III content]

---

## Win Themes Summary
[Table from Step 2]

---

## Recommended Next Step
[Specific CTA with proposed date]

Quality Gates

  • MEDDPICC 20+ confirmed before starting
  • Pain confirmed with at least 1 direct quote from discovery
  • Win themes map to confirmed decision criteria
  • Act I contains no product mentions
  • Act II capabilities map to confirmed pains (no orphaned features)
  • Act III uses buyer's own metrics from discovery (not generic benchmarks)
  • Executive summary stands alone in 90 seconds
  • Saved with today's date in meetings/ folder