sales-playbook

Sales Playbook

For unfamiliar placeholders or connected tools, see CONNECTORS.md.

B2B sales playbook. MEDDPICC methodology, Discovery → Close 5-stage process, core metrics, and team design to build repeatable, predictable sales engine.

How It Works

┌─────────────────────────────────────────────────────────────────┐
│                      SALES PLAYBOOK FRAMEWORK                    │
├─────────────────────────────────────────────────────────────────┤
│  Core Features (Standalone)                                      │
│  ✓ MEDDPICC 7 qualification criteria                            │
│  ✓ Discovery → Demo → Proposal → Negotiation → Close 5-stage   │
│  ✓ Sales metrics benchmark (Win Rate, Sales Cycle, ACV)         │
│  ✓ Sales team design (SDR/BDR, AE, CSM roles)                  │
├─────────────────────────────────────────────────────────────────┤
│  Enhanced Mode (with tool connections)                           │
│  + ~~CRM: Pipeline analysis, Win/Loss patterns                  │
│  + ~~calendar: Meeting scheduling, Sales Cycle tracking         │
│  + ~~email: Outreach sequences, auto follow-up                  │
└─────────────────────────────────────────────────────────────────┘

Getting Started

1. Qualification: "Use MEDDPICC to validate this deal"
2. Sales Process: "Help me prepare Discovery meeting"
3. Team Design: "How should we structure sales?"
4. Metrics: "Is our Win Rate normal?"

Sales Philosophy

Core Principles

1. Problem Solver, Not Product Pusher

   • Not: "Our product is the best"
   • But: "Here's how we solve your problem"

2. Sell Results, Not Features

   • Not: "AI-powered features"
   • But: "30% sales productivity increase"

3. Repeatable Process, Not Luck

   • Standardize top performer methods
   • Remove hero-dependent sales

4. Data-Based Forecast, Not Wishful

   • "Hopeful pipeline" is fantasy
   • Track, predict, execute

---

MEDDPICC Methodology

Overview

MEDDPICC: 7 qualification criteria. All met = 70%+ Win Rate

M - Metrics (Target numbers)
E - Economic Buyer (Final decision authority)
D - Decision Criteria (How they evaluate)
D - Decision Process (Steps to buy)
P - Identify Pain (Core problems)
C - Champion (Internal advocate)
C - Competition (What else they consider)

M - Metrics (Targets)

Definition: Quantitative goal customer wants to achieve

Questions:

• "What's your current [metric]?"
• "What's your target?"
• "What does closing this gap mean?"

Example:

• Current: 100 deals/month, 15% win rate
• Target: 200 deals/month, 25% win rate
• Impact: ₩20B additional revenue/year

Red Flag:

• ❌ No quantitative goal ("just improve")
• ❌ Vague target ("be more efficient")
• ❌ Unmeasurable ("feel better")

E - Economic Buyer (Final Authority)

Definition: Budget owner. The "yes" or "no" person.

Questions:

• "Who approves this budget?"
• "Does CFO get involved?"
• "What's the approval process?"

Decision Authority Levels:

Role	Authority	Budget	Contact
End User	Uses it	$0	Initial
Manager	Recommends	<$10K	Influencer
Director	Approves	$10-100K	Champion candidate
VP/C-level	Final yes/no	$100K+	Executive brief

Strategy:

• Multi-threading: Reach multiple levels
• Early EB Contact: Align early
• Champion Helps: Facilitate EB meeting

Red Flag:

• ❌ Haven't met Economic Buyer
• ❌ "Team lead decides" (but CFO actually does)
• ❌ EB uninterested

D - Decision Criteria (Evaluation Basis)

Definition: How they decide between options

Questions:

• "What's your selection criteria?"
• "How much weight each?"
• "Must-have vs nice-to-have?"

Typical Criteria:

1. Feature fit (30%)
2. Price (25%)
3. Integration ease (15%)
4. Vendor trust (15%)
5. Support (10%)
6. Implementation time (5%)

Strategy:

• Emphasize Our Strengths: Feature fit (30%), make it criteria
• Downplay Weaknesses: Price (25%), show ROI instead

D - Decision Process (Steps)

Definition: Buying process stages, timeline, participants

Questions:

• "What's your buying process?"
• "Each step takes how long?"
• "Who's involved?"

Typical Process:

1. Requirements (2 weeks) - End users, Manager
2. Vendor Eval (4 weeks) - Demo, POC; Manager, Director
3. Pricing/Negotiation (2 weeks) - Procurement, CFO
4. Legal Review (2 weeks) - Legal, Security
5. Final Approval (1 week) - C-level
6. Procurement (1 week) - PO issue

Total: 12 weeks (3 months)

Strategy:

• Reverse-Plan: Close goal - 12 weeks = start date
• Track Milestones: Each stage completed?
• Remove Blockers Early: Legal, Security issues

Red Flag:

• ❌ Unknowns: Legal, Security, Procurement steps
• ❌ Summer/year-end: Decision delays (vacations, budgets)
• ❌ Sudden halt: Priority shift, budget freeze

P - Identify Pain (Core Problem)

Definition: Customer's underlying problem to solve

Pain Hierarchy (3 Levels):

1. Symptom: "CRM is inconvenient"
2. Root Cause: "Sales team avoids data entry"
3. Business Impact: "No accurate forecast → CFO upset"

3 Why Questions:

1. "What problem do you have?" → "CRM inconvenient"
2. "Why is that a problem?" → "Sales won't enter data"
3. "What happens if not solved?" → "Forecast wrong → investment plan fails"

Pain Strength:

• Critical: Must fix now (business at risk)
• High: Fix in 3 months
• Medium: Fix in 6 months
• Low: "Nice to have" (no purchase)

Red Flag:

• ❌ Weak pain ("would be nice")
• ❌ Unknown cost (don't know damage)
• ❌ Alternatives exist (Excel works)

C - Champion (Internal Advocate)

Definition: Person inside pushing our solution

Characteristics:

• Our success = their benefit (promotion, KPI)
• Understands politics
• Accesses Economic Buyer
• Shares competitive intel

Champion vs Contact:

Champion	Contact
Pushes actively	Gathers info
Understands politics	Neutral
Connects to EB	Reports only
Takes risks	Safe position

Cultivate Champion:

• Provide ROI calculation (for their pitch)
• Internal deck (for their presentation)
• Success stories (proof)
• Executive brief (help close EB)

Red Flag:

• ❌ No champion
• ❌ Champion lacks influence (intern)
• ❌ Champion doesn't believe in us

C - Competition (Alternatives)

Definition: What else they're considering

Types:

1. Direct: Same category (Salesforce, HubSpot)
2. Indirect: Different way (Excel, custom)
3. Status Quo: Do nothing

Questions:

• "Looking at other solutions?"
• "How are you currently doing this?"
• "Compare pros/cons?"

Response:

## Competition
- **Vendor A**: Market leader, expensive
  - Strength: Brand, features
  - Weakness: $300/user (3x us)
  - Our counter: "Same value, 1/3 price"

- **Status Quo (Excel)**: Free
  - Weakness: Manual, error-prone
  - Our counter: "ROI: 500h saved = $50K/year"

Strategy:

• Use battlecard (see competitive-landscape)
• Value not feature comparison
• Avoid FUD (don't badmouth competitors)

---

5-Stage Sales Process

Stage Overview

Discovery → Demo → Proposal → Negotiation → Close
  (20%)     (30%)    (50%)       (70%)        (95%)

(Close probability by stage)

1. Discovery (20% Close Probability)

Goal: Understand MEDDPICC 7 elements

Duration: 1-2 meetings (60-90 mins each)

Preparation:

• Research company (website, LinkedIn)
• Identify competitor use
• Industry trend knowledge

Meeting Structure (60 mins):

1. Rapport (5 min): Relationship building
2. Agenda (2 min): Today's goal
3. Current State (15 min): Their situation
4. Future State (15 min): Ideal outcome
5. Impact (10 min): Gap cost
6. Process (10 min): Buying steps
7. Next Steps (3 min): Confirm Demo date

Core Questions:

• "How do you currently [process]?"
• "Biggest pain point?"
• "Ideally, how would it work?"
• "What if not fixed?"
• "Who decides? Timeline?"

Success Criteria:

• 5+ MEDDPICC elements understood
• Champion candidate identified
• Demo date confirmed

2. Demo (30% Close Probability)

Goal: Prove solution solves their pain

Duration: 1 meeting (45-60 mins)

Preparation:

• Review Discovery notes
• Design scenario (their pain-based)
• Use their data (mock if needed)

Demo Structure (45 mins):

1. Recap (5 min): Discovery summary
2. Demo (25 min): Scenario walkthrough
3. Q&A (10 min): Answer questions
4. Next Steps (5 min): Proposal discussion

Demo Principles:

• Show, Don't Tell: Live walkthrough
• Their Story: "Similar customer increased 30%"
• Pain → Solution: Directly solve their pain
• Hands-On: They click, not just watch

Anti-Patterns:

• ❌ Feature dump (all features listed)
• ❌ Generic demo (no customization)
• ❌ Monologue (45 mins you talking)

Success Criteria:

• "Aha moment" seen
• Technical questions (engagement)
• Champion will share with EB
• Proposal meeting scheduled

3. Proposal (50% Close Probability)

Goal: Present price, scope, timeline

Duration: 1 meeting + document

Proposal Structure:

# [Customer] Proposal

## Executive Summary (1 page)
Problem, Solution, Value (ROI)

## Scope of Work (1 page)
Features, Implementation, Training

## Pricing (1 page)
3 options (Good/Better/Best), Annual discount

## Case Study (1 page)
Similar customer success

## Next Steps (1 page)
Timeline, Contract, Onboarding

Pricing Presentation:

• 3 Options: High (anchor), Medium (target), Low (entry)
• Annual Emphasis: "20% savings"
• ROI Calculation: "12-month payback"

Meeting (60 mins):

1. Walkthrough (20 min): Document review
2. Questions (20 min): Concerns
3. Objection Handling (15 min): Price, competitors
4. Closing (5 min): "Ready to proceed?"

Success Criteria:

• Price agreed (within range)
• Legal/Procurement next
• Champion pitching EB

4. Negotiation (70% Close Probability)

Goal: Finalize terms, prepare contract

Duration: 1-3 weeks (email exchanges)

Negotiation Points:

Customer Request	Our Response	Condition
Price discount	5-10% OK	Annual commitment
Implementation help	Free onboarding	Reference customer
Custom feature	Prioritize roadmap	$X additional
Payment terms	Net 60 OK	3-year contract

Principles:

1. Give to Get: Never free, always exchange
2. Anchor High: First offer is high
3. Silence: Let them speak first
4. Walk-Away: Know minimum acceptable

Legal:

• MSA (Master Service Agreement)
• SLA (Service Level Agreement)
• DPA (Data Processing Agreement)

Success Criteria:

• Final price agreed
• Legal signed off
• PO (Purchase Order) date

5. Close (95% Close Probability)

Goal: Contract signed, payment, kick-off

Duration: 1 week

Checklist:

• Contract signed (DocuSign)
• PO received
• Payment received (advance or Net 30)
• Kickoff scheduled
• CSM assigned
• CRM marked "Won"

Kickoff Meeting:

• Implementation timeline
• Team introductions (AE → CSM handoff)
• 30-day goals

Win Analysis:

## Win: [Customer]
Deal Size: $[Amount]
Competitor: [Company]
Win Reasons:
1. [Reason 1] (40%)
2. [Reason 2] (35%)
3. [Reason 3] (25%)

Lesson: [Learning]

---

Key Sales Metrics

Win Rate (Success %)

Definition: Won ÷ Total Opportunities

Benchmarks:

Segment	Win Rate	Notes
SMB	20-30%	Fast decision
Mid-Market	25-35%	Medium complexity
Enterprise	30-40%	Long cycle

Improvement:

• Refine ICP (focus winning segment)
• Strict MEDDPICC (qualify out losers)
• Update battlecards

Sales Cycle (Days to Close)

Definition: Opportunity created → Close

Benchmarks:

Segment	Cycle	Notes
SMB	30-60 days	Quick
Mid-Market	60-120 days	Procurement involved
Enterprise	120-270 days	Legal, Security, many stakeholders

Shorten:

• Thorough Discovery (catch red flags late)
• EB early contact
• Legal templates pre-ready

ACV (Average Contract Value)

Definition: Average annual contract value

Benchmarks:

Segment	ACV
SMB	$5K-25K
Mid-Market	$25K-100K
Enterprise	$100K+

Optimize:

• Upsell (higher tier)
• Multi-year (3-year commitment)
• Add-ons (additional modules)

Pipeline Coverage

Definition: Total Pipeline ÷ Quarterly Quota

Target: 3-5x

Example:

Q Target: $500K
Pipeline: $2M
Coverage: 4x ✓

<3x Action:

• Accelerate new lead generation
• Hire SDR
• Marketing expansion

---

Sales Team Design

Roles

SDR/BDR (Sales/Business Development Rep)

Responsibility: Lead generation & qualification

Activities:

• Cold outreach (email, LinkedIn)
• Inbound lead response
• BANT qualification (Budget, Authority, Need, Timeline)
• Pass to AE

Metrics:

• SQL (Sales Qualified Lead): 20-30 monthly
• Conversion: 10-20%
• Activity: 50-100 touches daily

Compensation:

• Base: ₩30M + Variable: ₩15M
• Per-SQL bonus

AE (Account Executive)

Responsibility: Opportunity → Close

Activities:

• Discovery, Demo, Proposal
• MEDDPICC execution
• Negotiation

Metrics:

• Quota: $200-500K quarterly
• Win Rate: 25-35%
• Sales Cycle: 60-90 days

Compensation:

• Base: ₩60M + Commission: ₩60M (100% quota)
• OTE (On-Target Earnings): ₩120M

CSM (Customer Success Manager)

Responsibility: Onboarding, retention, expansion

Activities:

• Onboarding (first 30 days)
• Quarterly Business Reviews
• Renewal management
• Upsell/Cross-sell

Metrics:

• NRR (Net Revenue Retention): >110%
• Gross Churn: <10%/year
• Upsell: 30% of new ARR

Compensation:

• Base: ₩50M + Variable: ₩20M
• NRR, Renewal-based

Team Structure (By Stage)

Seed ($0-1M ARR):

• Founder-led sales
• 1-2 generalist AEs

Series A ($1-5M ARR):

• 1 Sales Lead
• 2-3 AEs
• 1 SDR (inbound)

Series B ($5-20M ARR):

• 1 VP Sales
• 6-8 AEs (segmented: SMB, Mid, Ent)
• 3-4 SDRs
• 2-3 CSMs

Hiring Criteria (AE)

• 3+ years related experience
• Similar ACV experience ($25K-100K)
• MEDDPICC or equivalent methodology
• Hunter mindset (self-driven)
• Coachability (willing to improve)

Onboarding (8 Weeks)

Week 1-2: Product

• Product training
• Demo practice (20 reps)
• ICP, persona deep-dive

Week 3-4: Shadowing

• Observe 10 Discovery calls
• Watch 5 demos

Week 5-6: Co-selling

• Your Discovery (observed)
• Feedback & coaching

Week 7-8: Solo

• Independent deals
• First close goal

90-Day Goals:

• Product expert
• First deal closed
• 50% of quota

Coaching (Ongoing)

1-on-1 Weekly:

• Deal review (MEDDPICC)
• Pipeline health
• Skill improvement

Team Meeting Weekly:

• Win/Loss sharing
• Best practices
• Competitor updates

Training Monthly:

• External trainers
• Role plays
• New feature training

---

Related Skills

• gtm-strategy: Sales-Led GTM motion design
• pricing-strategy: Price negotiation tactics
• competitive-landscape: Battlecard usage
• investor-research: Apply MEDDPICC to VC sales

Tips

• MEDDPICC Strict: 5+ criteria met? Otherwise walk
• Multi-thread: Never 1-person relationship
• Champion Critical: No champion = <10% win
• Discovery is 80%: Win/loss decided here
• Feature → Value: "30% time saved" not "AI features"
• Objections = Interest: Questions = good sign
• Silence Wins: Price stated, stay quiet
• Process > Talent: Standardize top performer
• Track Win/Loss: Patterns inform product/marketing