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sales-playbook

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.

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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:

DimensionQuestion
MetricsWhat measurable outcomes does the customer expect?
Economic BuyerWho has budget authority? Have we engaged them?
Decision CriteriaWhat technical/business criteria drive the decision?
Decision ProcessWhat are the steps, timeline, and approvals needed?
Paper ProcessWhat legal/procurement steps are required to close?
Implicate the PainWhat happens if they do nothing? Is the pain urgent?
ChampionWho inside is selling on our behalf? Can they mobilize?
CompetitionWho 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

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