espennilsen/sales-playbook

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