ceo-advisor

name	ceo-advisor
description	Executive leadership guidance for startup CEOs. Use when the user mentions strategy, fundraising, pitch deck, board meetings, investor relations, pivoting, vision, stakeholder communication, capital allocation, organizational culture, crisis management, succession planning, or any CEO-level decision making. Also triggers on: CEO, strategic planning, board prep, investor update, organizational leadership, executive strategy, annual planning, OKRs, company direction, zero to one, contrarian thinking, monopoly strategy, Peter Thiel, power law, team leadership, A-player hiring, first 10 hires, delegation, culture building, firing decisions.
user-invocable	false

CEO Advisor

Strategic leadership frameworks for vision, fundraising, board management, culture, and stakeholder alignment. Built for startup CEOs navigating from pre-seed through Series B+.

Keywords

CEO, chief executive officer, strategy, strategic planning, fundraising, board management, investor relations, culture, organizational leadership, vision, mission, stakeholder management, capital allocation, crisis management, succession planning, pitch deck, board deck, annual plan, OKRs, pivot, company direction

Core Responsibilities

1. Vision & Strategy

Set the direction — 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 leadership team
• Monthly: Strategy health check — are we still on track?

Stage-adaptive time horizons:

Stage	Short-term	Medium-term	Long-term
Pre-seed/Seed	3 months	6 months	12 months
Series A	6 months	1 year	2 years
Series B+	1 year	3 years	5 years

Strategic decision framework (DECIDE):

• Define the problem clearly
• Establish criteria for solutions
• Consider alternatives
• Identify best alternatives
• Develop and implement action plan
• Evaluate and monitor solution

See references/strategy-advisor.md for full strategic analysis frameworks.

2. Capital & Resource Management

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

Capital allocation priorities:

1. Essential (40-50%) — Operations, compliance, security
2. Strategic (30-40%) — Growth initiatives, competitive advantage
3. Efficiency (10-15%) — Cost reduction, productivity
4. Experimental (5-10%) — Innovation, R&D, new bets

Budget decision tree:

• Required for operations? → Auto-approve
• Drives growth with >30% ROI? → Strategic approve
• Reduces costs with <12 month payback? → Efficiency approve
• Everything else? → Limited experimental budget

3. Fundraising

Know your numbers cold. Timing matters more than valuation.

Key fundraising metrics to know:

• MRR/ARR and growth rate
• Burn rate and runway (months)
• CAC, LTV, and LTV:CAC ratio
• Net Revenue Retention
• TAM/SAM/SOM (bottom-up)

Process: See references/fundraising.md for full fundraising playbook. Materials: Use /imperium:pitch-deck and /imperium:fundraise-prep commands.

4. Board & Investor Management

Your board can be your greatest asset or your biggest liability.

Board meeting cadence:

• Quarterly board meetings (materials sent 3 days ahead)
• Monthly investor updates (see references/board-prep.md)
• Ad hoc calls for major decisions

Board deck structure: See references/board-prep.md for the full board meeting prep framework.

5. Organizational Culture

Culture is what people do when you're not in the room.

Culture development:

• Define values (3-5, specific and actionable)
• Model them personally (visible and consistent)
• Hire for them (culture add, not culture fit)
• Enforce them (address violations immediately)
• Celebrate them (recognize people who embody values)

6. Crisis Management

Immediate (0-2 hours): Activate crisis team, assess severity, contain, notify stakeholders Short-term (2-24 hours): Response strategy, public statements, legal/regulatory, employee communication Recovery (24+ hours): Implement solution, full stakeholder communication, post-mortem

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
People	Employee engagement	>7/10	Quarterly
Personal	% time on strategic work	>40%	Weekly

Key Questions a CEO Should Ask

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

Red Flags

• You're the bottleneck for >3 decisions per week
• Burn multiple rising while growth slows
• Board surprises (they should never learn bad news in the meeting)
• Strategic plan exists but nobody references it
• Key hires leaving in first 6 months

Reference Files

• references/strategy-advisor.md — Strategic analysis frameworks, SWOT, Porter's, scenario planning
• references/board-prep.md — Board meeting preparation, investor communication, board deck structure
• references/fundraising.md — Fundraising playbook, term sheets, valuation, data room
• references/pitch-deck.md — Pitch deck creation, narrative arc, stage-specific adjustments
• references/decision-frameworks.md — Decision matrices, Go/No-Go criteria, capital allocation
• references/contrarian-strategy.md — Zero-to-one thinking, monopoly vs competition, power law, secrets (Source: Zero to One)
• references/team-leadership.md — A-player hiring, first 10 hires, delegation framework, culture building