Ceo advisor
CEO, CTO, CMO, CFO, sales, product & legal advisors — all in one Claude Code plugin. 250+ skills from 10 distilled startup books. Install once, run your startup smarter.
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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.
SKILL.md
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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:
- Essential (40-50%) — Operations, compliance, security
- Strategic (30-40%) — Growth initiatives, competitive advantage
- Efficiency (10-15%) — Cost reduction, productivity
- 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 planningreferences/board-prep.md— Board meeting preparation, investor communication, board deck structurereferences/fundraising.md— Fundraising playbook, term sheets, valuation, data roomreferences/pitch-deck.md— Pitch deck creation, narrative arc, stage-specific adjustmentsreferences/decision-frameworks.md— Decision matrices, Go/No-Go criteria, capital allocationreferences/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