Deal Strategy

Build a win plan for any strategic deal. AI produces competitive landscape analysis, stakeholder influence maps, value proposition alignment, and a milestone timeline with risk mitigation.

Skill Details

Install this skill

Versionv1.0.0AuthorJorge ArteagaLicenseMITSections20

Works with

Claude CodeCursorWindsurf

When This Skill Owns the TaskWorkflow

Required Context to Gather FirstWorkflow

Before building a win plan, ask for or infer:

Deal overview — Company, opportunity name, ARR/TCV, target close date

Current stage — Where are we in the sales cycle?

MEDDIC status — What do we know? (Pull from sf-se-qualification if available)

Competitive situation — Who else is in the deal?

Stakeholder map — Who are the key players and their attitudes?

Value proposition fit — What have we proposed and how has it been received?

Key risks — What are the 2-3 things most likely to prevent us from winning?

SE time investment so far — Hours invested; what's still needed?

WorkflowWorkflow

Assess current deal state — Summarize MEDDIC completeness and top qualification gaps.

Map the competitive landscape — Who are we against, and what's our differentiated position?

Align value to decision criteria — Connect each decision criterion to specific Salesforce strengths.

Identify deal risks — Technical, commercial, organizational, and competitive.

Build the milestone map — Sequence the activities needed to close by the target date.

Define the SE engagement plan — What specifically does the SE need to do to advance this deal?

Produce the win plan document — Use the output template below.

Review with AE and leadership — The win plan is a living document; update it weekly.

Core Frameworks

The Win Plan Framework

A win plan answers five questions:

Code

1. WHY WON'T WE WIN?
   The most honest part of the plan. If you can't name what could lose this deal,
   you don't understand it well enough to win it.

2. WHY WILL WE WIN?
   Your specific, differentiated advantages for THIS customer. Not generic Salesforce strengths.

3. WHO DO WE NEED TO WIN OVER?
   The 1-2 people whose support is critical and whose current attitude is uncertain.

4. WHAT DO WE NEED TO PROVE?
   The 1-2 things the customer still needs to believe before they'll buy.

5. WHAT HAS TO HAPPEN BY WHEN?
   The specific milestone sequence that gets us to a signature.

Deal Risk Classification

Assess every strategic deal across these four risk dimensions:

The Milestone Sequence (Path to Close)

Map backwards from the target close date:

CLOSE DATE (Contract signed)
      ↑
Legal / Procurement review (allow 2-4 weeks)
      ↑
Commercial proposal delivered and accepted
      ↑
Executive alignment / sponsor sign-off
      ↑
Technical validation complete (POC, architecture review, or deep-dive)
      ↑
Champion confirmed; EB engaged
      ↑
Decision criteria fully mapped and addressed
      ↑
Discovery complete; pain validated and quantified
      ↑
TODAY

SE Role in a Strategic Deal

The SE's highest-value activities at each stage:

Output FormatTemplate

Win Plan Document

MARKDOWN

# Win Plan — [Company Name] | [Opportunity Name]
**Date:** [Date] | **Close Target:** [Date] | **ARR:** $[X] | **Stage:** [Stage]
**AE:** [Name] | **SE:** [Name] | **RVP/Manager:** [Name]

---

## Deal Snapshot
- **Why are they buying?** [The compelling event or trigger]
- **What are they buying?** [Products and scope]
- **When do they need to go live?** [Implementation timeline]

---

## Why We'll Win (Our Differentiated Advantages)
1. [Specific advantage for THIS customer — not generic Salesforce]
2. [Specific advantage]
3. [Specific advantage]

---

## Why We Might Lose (Honest Risk Assessment)
1. [Specific risk and why it threatens the deal]
2. [Specific risk]
3. [Specific risk]

---

## Qualification Snapshot

| MEDDIC Element | Status | Evidence | Gap? |
|---------------|--------|---------|------|
| Metrics | ✓/✗/Partial | [Evidence] | [Action needed] |
| Economic Buyer | ✓/✗/Partial | [Evidence] | [Action needed] |
| Decision Criteria | ✓/✗/Partial | [Evidence] | [Action needed] |
| Decision Process | ✓/✗/Partial | [Evidence] | [Action needed] |
| Identify Pain | ✓/✗/Partial | [Evidence] | [Action needed] |
| Champion | ✓/✗/Partial | [Evidence] | [Action needed] |

**Overall Deal Score:** [X/60] — [GREEN / YELLOW / RED]

---

## Competitive Landscape

| Competitor | Status | Their Strengths | Our Counter |
|-----------|--------|-----------------|------------|
| [Competitor] | Active / Eliminated / Unknown | [Their pitch] | [Our response] |

**Bottom line:** [Who is currently winning and why]

---

## Value-to-Criteria Alignment

| Their Decision Criterion | Our Response | Evidence |
|------------------------|-------------|---------|
| [Criterion 1] | [How we address it] | [Proof point] |
| [Criterion 2] | [How we address it] | [Proof point] |

---

## Stakeholder Summary

| Name | Title | Attitude | Our Influence | Risk |
|------|-------|---------|--------------|------|
| [Name] | [Title] | Champion / Neutral / Skeptic | H/M/L | [Description] |

**Who we still need to win over:** [Name, why, and how]

---

## What We Need to Prove

The 1-2 things the customer must believe before they'll buy:
1. [Specific belief we need to create or validate]
2. [Specific belief]

**How we'll prove it:** [Specific action — POC, reference call, architecture review]

---

## Risk Register

| Risk | Probability | Impact | Mitigation |
|------|------------|--------|-----------|
| [Risk] | H/M/L | H/M/L | [Action] |

---

## Milestone Map

| Milestone | Target Date | Owner | Status |
|-----------|------------|-------|--------|
| Discovery complete | [Date] | SE + AE | Done / In Progress / Not Started |
| Champion confirmed | [Date] | AE | |
| Technical validation complete | [Date] | SE | |
| EB meeting scheduled | [Date] | AE | |
| Business case delivered | [Date] | SE + AE | |
| Proposal submitted | [Date] | AE | |
| Executive alignment | [Date] | AE + RVP | |
| Legal / Procurement start | [Date] | AE | |
| **Contract signed** | **[Close Date]** | **AE** | |

---

## SE Engagement Plan

| Activity | Owner | Due | Purpose |
|----------|-------|-----|---------|
| [SE activity] | SE | [Date] | [Why this activity advances the deal] |

**SE hours committed to this deal:** [X hours remaining in quarter]

---

## Weekly Deal Health

*Updated [Date]:*
[1-2 sentence deal health summary: what happened this week, what changed, what's next]

Anti-PatternsReference

Scoring Rubric (100 Points)Reference

Score Guide:

85-100: Deal is well-managed. Advance with confidence.
65-84: Solid plan with gaps. Address the lowest-scoring area before next meeting.
45-64: Deal at risk. Escalate and review with leadership.
Below 45: Not enough known to win. Consider qualify-out.

Cross-Skill IntegrationReference

Task	This Skill	Defer To
Build a deal win plan	Yes	—
Assess deal risk and identify mitigation actions	Yes	—
Map the path to close with milestones	Yes	—
Align value proposition to decision criteria	Yes	—
Score the deal with MEDDIC	No	sf-se-qualification
Map specific stakeholder influence	No	sf-se-stakeholder-mapping
Build the business case	No	sf-se-proof-of-value
Research competitive positioning	No	sf-se-competitive
Risk Type	High Risk Signals	Medium Risk	Low Risk
Technical	Unproven integration; hard migration; compliance gaps	Some technical questions open	Architecture reviewed; poc successful
Organizational	No champion; champion low-powered; EB not engaged	Champion confirmed but limited access to EB	Strong champion with direct EB access
Commercial	Budget not confirmed; competing with status quo	Budget cycle unclear; CFO not engaged	Budget approved; financial impact quantified
Competitive	Incumbent competitor with executive relationships	Level playing field	Clear preference for Salesforce; competitor disadvantaged
Stage	SE Role	Key Activity
Early Discovery	Technical credibility	Architecture conversations; technical discovery
Evaluation	Proof and differentiation	PoC / demo tailored to decision criteria
Validation	Risk reduction	Architecture review; security Q&A; reference calls
Business Case	Quantified value	ROI model; PoV document
Close	Executive alignment	Technical briefings for CTO/CIO; risk mitigation
Post-Sale	Smooth handoff	Handoff document; delivery team enablement
Anti-Pattern	Why It Fails	Fix
Win plans that only describe what's happened	A plan that describes the past isn't a plan; it's a log	Win plans answer "what will we do next" not "what have we done"
Not doing the "why we'll lose" exercise	Optimism bias; the team focuses on strengths and ignores the kill shots	Force rank the top 3 risks; assign owners to mitigate each
Milestones with no owners	Tasks without owners don't get done; the deal drifts	Every milestone needs a named owner and a date
SE engagement plan that's "available as needed"	Reactive SE involvement; critical activities fall through the cracks	Proactively map SE activities to deal stages; commit to specific deliverables
Win plan created once and never updated	The deal changes; the plan doesn't; it becomes irrelevant	Update the win plan after every material customer touchpoint
Generic value propositions not linked to decision criteria	The customer doesn't see the connection between your strengths and what they care about	Map every advantage explicitly to a stated decision criterion
Category	Points	Pass Criteria
Risk Honesty	20	At least 3 specific risks named with mitigations (not vague concerns)
MEDDIC Completeness	25	At least 4/6 MEDDIC elements confirmed with evidence
Milestone Map	25	Full sequence from today to close with owners and dates
Value-Criteria Alignment	15	Every stated decision criterion has a Salesforce response and proof
SE Engagement Plan	15	Specific SE activities mapped to deal stages with hours committed
Skill	When to Use It
sf-se-qualification	Source the MEDDIC data that feeds the win plan
sf-se-stakeholder-mapping	Build the detailed stakeholder section
sf-se-competitive	Build the competitive landscape section
sf-se-proof-of-value	Build the business case component
sf-se-executive-briefing	Prepare for the executive alignment milestone
sf-se-handoff	Create the handoff document when the deal closes