Sales Playbooks, Financial Models & Org Charts

Operational Documents vs. Communication Documents

The previous lessons covered communication documents — things you show to external audiences to persuade. This lesson covers operational documents — things your team uses internally to execute.

The difference matters for prompting. Communication documents need polish, narrative, and persuasion. Operational documents need precision, completeness, and clarity.

Founder Equity Strategy

What it is: A structured plan for how equity is allocated, vested, and managed across founders, employees, and investors.

What it must contain:

• Founding equity split and rationale
• Vesting schedule (standard: 4-year / 1-year cliff)
• Option pool size and refresh policy
• Dilution modeling across funding rounds
• Advisor equity guidelines (standard: 0.1%–0.5%)
• Key person provisions

Claude workflow:

I'm a 2-person founding team. We have a technical co-founder (60% of early work)
and a business co-founder (40% of early work). We expect to raise a seed round
of $2M at $8M pre-money. Generate an equity strategy document including:
- Recommended founding split with justification
- Vesting schedule
- Option pool sizing for seed stage
- Projected cap table after seed round
- Standard advisor equity terms
Note clearly which numbers are assumptions that need legal review.

Important: All equity documents must be reviewed by a qualified startup attorney before execution. Claude generates frameworks and structures; legal counsel executes them correctly.

---

Financial Model Structure

A financial model is not a spreadsheet — it's a set of structured assumptions that drive a projection. Claude helps you define those assumptions and create the model architecture.

What a financial model must contain:

• Revenue model (pricing × volume × conversion rates)
• Cost of goods sold / cost of revenue
• Operating expenses by department
• Headcount plan
• Cash flow projection
• Key metrics dashboard (CAC, LTV, burn rate, runway)
• Scenario modeling (base, bull, bear)

Claude prompt for model structure:

Build a financial model structure for a B2B SaaS company with the following characteristics:
- Pricing: $299/month per seat
- Sales motion: outbound + inbound
- Team: 3 people today, scaling to 12 in 18 months
- Target: $1M ARR in 24 months

Generate a list of all model inputs (assumptions), all calculated outputs,
and the formulas linking them. Flag which assumptions are most sensitive
to outcome variation.

Using Claude for scenario analysis:

My base case assumes 15 new customers per month at $299/month with 3% monthly churn.
Generate a sensitivity table showing ARR at 24 months if:
- New customers/month varies: 10, 15, 20, 25
- Monthly churn varies: 1.5%, 3%, 5%
Show as a matrix. Identify the scenario combinations that hit $1M ARR.

---

Organizational Chart Documentation

An org chart document goes beyond boxes and lines — it defines roles, responsibilities, and reporting structures in a way that scales.

What an org chart document must contain:

• Current org structure with reporting lines
• Role descriptions for each position
• Decision authority matrix (who decides what)
• Planned future state (next 12 months)
• Open roles and hiring priority

Claude prompt:

We are a 6-person startup: 1 CEO, 1 CTO, 2 engineers, 1 sales rep, 1 customer success manager.
Generate an organizational chart document including:
- Current structure with reporting lines
- 1-paragraph role description for each position
- A RACI matrix for our top 5 business decisions
- Recommended next 3 hires with justification
- Future org structure at 20 people

---

Founder Equity Strategy vs. Employee Equity Policy

These are two distinct documents. The equity strategy covers founders and cap table management. The employee equity policy covers how you grant and communicate equity to team members.

Employee equity policy must contain:

• Option pool overview and refresh policy
• Grant levels by role and seniority
• Vesting schedule and acceleration terms
• Exercise window after departure
• How equity is communicated during hiring

Generate an employee equity policy for a seed-stage startup with a 10% option pool.
Include grant levels for engineering (IC1-IC4), product, design, and sales roles.
Use market benchmarks. Explain each provision in plain language suitable for
non-technical hires who have never received equity before.

Key Takeaways

• Operational documents prioritize precision and completeness over persuasion
• Claude generates structure and frameworks; human experts supply legal and financial accuracy
• Always include "flag assumptions that need expert review" in financial and legal document prompts
• Scenario modeling is a high-value use case — Claude can enumerate combinations faster than manual work

---

Try It Yourself: Write a prompt asking Claude to generate a headcount plan for a 15-person startup scaling to 30 in 18 months. Specify the current team composition and the strategic priorities for the next year. Evaluate whether the recommended hires are prioritized correctly given your actual business goals.