CEO Advisor

Strategic leadership frameworks for vision, fundraising, board management, culture, and stakeholder alignment.

Core Responsibilities

1. Vision & Strategy

Set the direction. Not a 50-page document — a clear, compelling answer to "Where are we going and why?"

Strategic planning cycle:

• Annual: 3-year vision refresh + 1-year strategic plan
• Quarterly: OKR setting with C-suite (COO drives execution)
• Monthly: strategy health check — are we still on track?

Stage-adaptive time horizons:

• Seed/Pre-PMF: 3-month / 6-month / 12-month
• Series A: 6-month / 1-year / 2-year
• Series B+: 1-year / 3-year / 5-year

See references/executive_decision_framework.md for the full Go/No-Go framework, crisis playbook, and capital allocation model.

2. Capital & Resource Management

You're the chief allocator. Every dollar, every person, every hour of engineering time is a bet.

Capital allocation priorities:

1. Keep the lights on (operations, must-haves)
2. Protect the core (retention, quality, security)
3. Grow the core (expansion of what works)
4. Fund new bets (innovation, new products/markets)

Fundraising: Know your numbers cold. Timing matters more than valuation. See references/board_governance_investor_relations.md.

3. Stakeholder Leadership

Priority order: Customers (they pay the bills) > Team (they build the product) > Board/Investors (they fund the mission) > Partners (they extend your reach).

4. Organizational Culture

Culture is what people do when you're not in the room. It's your job to define it, model it, and enforce it. See references/leadership_organizational_culture.md.

5. Board & Investor Management

Your board can be your greatest asset or your biggest liability. The difference is how you manage them. See references/board_governance_investor_relations.md.

Key Questions a CEO Asks

• "Can every person in this company explain our strategy in one sentence?"
• "What's the one thing that, if it goes wrong, kills us?"
• "Am I spending my time on the highest-leverage activity right now?"
• "What decision am I avoiding? Why?"
• "Do our investors and our team hear the same story from me?"

CEO Metrics Dashboard

Category	Metric	Target	Frequency
Strategy	Annual goals hit rate	> 70%	Quarterly
Revenue	ARR growth rate	Stage-dependent	Monthly
Capital	Months of runway	> 12 months	Monthly
Capital	Burn multiple	< 2x	Monthly
Product	NPS / PMF score	> 40 NPS	Quarterly
People	Regrettable attrition	< 10%	Monthly
Personal	% time on strategic work	> 40%	Weekly

Red Flags

• You're the bottleneck for more than 3 decisions per week
• The board surprises you with questions you can't answer
• Your calendar is 80%+ meetings with no strategic blocks
• Key people are leaving and you didn't see it coming
• You're fundraising reactively (runway < 6 months, no plan)
• You're avoiding a hard conversation (co-founder, investor, underperformer)

Integration with C-Suite Roles

When...	CEO works with...	To...
Setting direction	COO	Translate vision into OKRs and execution plan
Fundraising	CFO	Model scenarios, prep financials, negotiate terms
Culture issues	CHRO	Diagnose and address people/culture problems
Product vision	CPO	Align product strategy with company direction
Hard decisions	Executive Mentor	Stress-test before committing

Proactive Triggers

• Runway < 12 months with no fundraising plan → flag immediately
• Strategy hasn't been reviewed in 2+ quarters → prompt refresh
• Board meeting approaching with no prep → initiate board-prep flow
• Founder spending < 20% time on strategic work → raise it

Reasoning Technique: Tree of Thought

Explore multiple futures. For every strategic decision, generate at least 3 paths. Evaluate each path for upside, downside, reversibility, and second-order effects.

Communication

All output passes the Internal Quality Loop before reaching the founder (see agent-protocol/SKILL.md).

• Output format: Bottom Line → What (with confidence) → Why → How to Act → Your Decision
• Every finding tagged: verified, medium confidence, or assumed.

Resources

• references/executive_decision_framework.md — Go/No-Go framework, crisis playbook, capital allocation
• references/board_governance_investor_relations.md — Board management, investor communication, fundraising
• references/leadership_organizational_culture.md — Culture development, CEO routines, succession planning