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
1---2name: sales-playbook3description: 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.4---56# Sales Playbook78Build sales artifacts grounded in MEDDPICC methodology and Espen's enterprise AI sales experience.910## Artifacts This Skill Produces1112- **MEDDPICC Deal Analysis** — Qualify a deal against all 8 dimensions13- **Sales Playbook** — Repeatable motion for a product/segment14- **Outreach Sequence** — Multi-touch cadence (email, LinkedIn, call)15- **Customer Deck Outline** — Slide structure with talking points16- **Objection Handling Guide** — Common objections with responses17- **Pipeline Review Brief** — Summary + recommendations for a deal set1819## MEDDPICC Framework2021For every deal analysis, score each dimension (1-3: weak/moderate/strong) and identify gaps:2223| Dimension | Question |24|-----------|----------|25| **Metrics** | What measurable outcomes does the customer expect? |26| **Economic Buyer** | Who has budget authority? Have we engaged them? |27| **Decision Criteria** | What technical/business criteria drive the decision? |28| **Decision Process** | What are the steps, timeline, and approvals needed? |29| **Paper Process** | What legal/procurement steps are required to close? |30| **Implicate the Pain** | What happens if they do nothing? Is the pain urgent? |31| **Champion** | Who inside is selling on our behalf? Can they mobilize? |32| **Competition** | Who else is being evaluated? What's our differentiation? |3334## Playbook Template3536When creating a playbook, use this structure:3738```markdown39# [Product/Segment] Sales Playbook4041## Ideal Customer Profile42- Industry, size, tech stack, pain signals4344## Value Proposition45- 1-sentence elevator pitch46- 3 key differentiators vs. status quo47- 3 key differentiators vs. competition4849## Discovery Questions50- 5-7 open questions that uncover MEDDPICC dimensions5152## Objection Handling53| Objection | Response Framework |54|-----------|-------------------|5556## Proof Points57- Customer stories, metrics, case studies5859## Competitive Positioning60- Feature comparison, narrative reframes6162## Sales Motion63- Prospecting → Discovery → Demo → Proposal → Close64- Time-to-close benchmark, typical deal size65```6667## Outreach Sequence Template6869```markdown70# [Campaign Name] Outreach Sequence7172## Target Persona73Role, industry, pain points, trigger events7475## Sequence (10-14 days)76### Day 1 — Email 1: Pain-led hook77### Day 3 — LinkedIn connect + note78### Day 5 — Email 2: Social proof79### Day 8 — Call attempt + voicemail80### Day 10 — Email 3: Insight share81### Day 14 — Email 4: Break-up8283## Personalization Variables84- {{company_pain}}, {{relevant_metric}}, {{mutual_connection}}85```8687## Guidelines8889- Always tie features to **business outcomes**, not technical specs90- Use the customer's language, not vendor jargon91- Every claim needs a proof point (number, customer name, or case study)92- Playbooks should be usable by a rep on day 1, not just by Espen93- Keep outreach under 100 words per touch — respect the reader's time
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