Sales
Core Principle
Sales isn't convincing people to buy something they don't want. It's finding people who already have the problem and showing them a better path.
Founder-Led Sales → Scalable Engine
The Four Stages
Stage 1: Founder closes every deal (0-10 customers)
→ Learn the sales motion, objections, and buying triggers
Stage 2: Founder + first hire (10-30 customers)
→ Document the playbook, hire someone to run it
Stage 3: Small team with process (30-100 customers)
→ Repeatable pipeline, CRM discipline, weekly metrics
Stage 4: Scalable engine (100+ customers)
→ Specialized roles (SDR, AE, CS), quota-based management
Methodology Selection
Match the Method to the Situation
| Situation | Methodology | Why |
|---|---|---|
| Complex enterprise, $50K+ ACV | MEDDIC | Multiple stakeholders, long cycles need qualification rigor |
| Quick SMB qualification, < $10K ACV | BANT | Fast yes/no decision on whether to pursue |
| Differentiated product, new category | Challenger | You need to teach buyers why the status quo is risky |
| Transactional, high volume | SPIN | Surface pain through questions, move fast |
MEDDIC Framework (Enterprise)
M — Metrics: What's the measurable impact of solving this?
E — Economic Buyer: Who signs the check?
D — Decision Criteria: What are they evaluating on?
D — Decision Process: What are the steps to close?
I — Identify Pain: What specific pain drives this purchase?
C — Champion: Who inside will fight for you?
BANT Framework (SMB)
B — Budget: Do they have money allocated?
A — Authority: Am I talking to the decision maker?
N — Need: Is the pain urgent enough to act?
T — Timeline: When do they need this solved?
Disqualify fast: If 2+ are missing, move on.
Challenger Sale (New Categories)
1. Teach — Share an insight they didn't know about their problem
2. Tailor — Connect the insight to their specific situation
3. Take control — Guide the buying process, don't be passive
Cold Outreach Sequences
Email Sequence (5 touches over 14 days)
Day 1: Pain-based opener (no pitch)
Subject: "[Specific pain point] at [Company]?"
Body: 2-3 sentences about the problem. One question.
Day 3: Value proof
Subject: Re: [previous subject]
Body: "Company X solved this and saw [result]. Here's how."
Day 7: Different angle
Subject: New subject line, different pain point or persona
Body: Brief case study or metric. Soft CTA.
Day 10: Breakup preview
Subject: "Should I close your file?"
Body: "Seems like timing isn't right. Wanted to check before I stop reaching out."
Day 14: Breakup
Subject: "Closing the loop"
Body: "Moving on, but here's [resource] in case it's helpful later."
Target Metrics
| Metric | Target | Red Flag |
|---|---|---|
| Open rate | 40-60% | < 25% (subject lines need work) |
| Reply rate | 8-15% | < 5% (messaging or targeting issue) |
| Meeting booked rate | 3-5% of sequence | < 1% (revisit ICP or value prop) |
| Show rate | 80%+ | < 60% (confirmation flow broken) |
LinkedIn Outreach (Parallel Track)
Day 0: View their profile
Day 1: Connect request (no note or very brief note)
Day 3: After connection, send a relevant insight (not a pitch)
Day 7: Share content relevant to their challenge
Day 10: Soft ask for conversation
Pipeline Management
Stage → Criteria to advance → Probability
Prospecting → Identified as ICP match → 10%
Discovery → Pain confirmed, stakeholder → 20%
Evaluation → Demo given, criteria met → 40%
Proposal → Pricing delivered → 60%
Negotiation → Terms under discussion → 80%
Closed Won → Signed → 100%
Anti-Patterns
| Sales Theater | Real Sales |
|---|---|
| "Let me show you our features" | "Tell me about [their problem]" |
| Pitching in the first email | Leading with insight or a question |
| "Following up" with no new value | Each touch adds a new angle or proof point |
| No CRM, deals in your head | Every deal tracked with stage and next action |
| Discounting to close | Selling value, walking away if fit isn't there |
Power Move
"Design a complete outbound sequence for [ICP] selling [product at $X ACV]. Choose the right methodology (MEDDIC, BANT, or Challenger), write the 5-email sequence, define pipeline stages, and set the target metrics I should track weekly."
The agent becomes your sales architect — building a repeatable process, not just individual pitches.