sales-playbook

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Create and refine sales playbooks, deal strategies, MEDDPICC analyses, customer decks, and outreach sequences. Use for any sales methodology work, pipeline review, or go-to-market planning.

espennilsen By espennilsen schedule Updated 2/17/2026

name: sales-playbook description: Create and refine sales playbooks, deal strategies, MEDDPICC analyses, customer decks, and outreach sequences. Use for any sales methodology work, pipeline review, or go-to-market planning.

Sales Playbook

Build sales artifacts grounded in MEDDPICC methodology and Espen's enterprise AI sales experience.

Artifacts This Skill Produces

  • MEDDPICC Deal Analysis — Qualify a deal against all 8 dimensions
  • Sales Playbook — Repeatable motion for a product/segment
  • Outreach Sequence — Multi-touch cadence (email, LinkedIn, call)
  • Customer Deck Outline — Slide structure with talking points
  • Objection Handling Guide — Common objections with responses
  • Pipeline Review Brief — Summary + recommendations for a deal set

MEDDPICC Framework

For every deal analysis, score each dimension (1-3: weak/moderate/strong) and identify gaps:

Dimension Question
Metrics What measurable outcomes does the customer expect?
Economic Buyer Who has budget authority? Have we engaged them?
Decision Criteria What technical/business criteria drive the decision?
Decision Process What are the steps, timeline, and approvals needed?
Paper Process What legal/procurement steps are required to close?
Implicate the Pain What happens if they do nothing? Is the pain urgent?
Champion Who inside is selling on our behalf? Can they mobilize?
Competition Who else is being evaluated? What's our differentiation?

Playbook Template

When creating a playbook, use this structure:

# [Product/Segment] Sales Playbook

## Ideal Customer Profile
- Industry, size, tech stack, pain signals

## Value Proposition
- 1-sentence elevator pitch
- 3 key differentiators vs. status quo
- 3 key differentiators vs. competition

## Discovery Questions
- 5-7 open questions that uncover MEDDPICC dimensions

## Objection Handling
| Objection | Response Framework |
|-----------|-------------------|

## Proof Points
- Customer stories, metrics, case studies

## Competitive Positioning
- Feature comparison, narrative reframes

## Sales Motion
- Prospecting → Discovery → Demo → Proposal → Close
- Time-to-close benchmark, typical deal size

Outreach Sequence Template

# [Campaign Name] Outreach Sequence

## Target Persona
Role, industry, pain points, trigger events

## Sequence (10-14 days)
### Day 1 — Email 1: Pain-led hook
### Day 3 — LinkedIn connect + note
### Day 5 — Email 2: Social proof
### Day 8 — Call attempt + voicemail
### Day 10 — Email 3: Insight share
### Day 14 — Email 4: Break-up

## Personalization Variables
- {{company_pain}}, {{relevant_metric}}, {{mutual_connection}}

Guidelines

  • Always tie features to business outcomes, not technical specs
  • Use the customer's language, not vendor jargon
  • Every claim needs a proof point (number, customer name, or case study)
  • Playbooks should be usable by a rep on day 1, not just by Espen
  • Keep outreach under 100 words per touch — respect the reader's time
Install via CLI
npx skills add https://github.com/espennilsen/pi --skill sales-playbook
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