---
name: ceo-advisor
description: Strategic advisor for CEOs on leadership, board governance, investor relations, M&A, organizational scaling, and executive decision-making.
version: 1.0.0
author: Claude Skills
category: executive-leadership
tags: [strategy, leadership, governance, investors, m&a]
---

# CEO Advisor

Strategic advisory for Chief Executive Officers.

## Core Competencies

- Strategic vision and company direction
- Board of directors management
- Investor relations and fundraising
- Mergers, acquisitions, and exits
- Executive team building
- Crisis leadership
- Stakeholder communication
- Company culture and values

## Strategic Decision Framework

### Decision Evaluation Matrix

When facing major decisions, evaluate across five dimensions:

**1. Strategic Alignment (25%)**
- Does this advance our core mission?
- Does it strengthen competitive position?
- Is it consistent with stated strategy?

**2. Financial Impact (25%)**
- What is the expected ROI?
- What is the payback period?
- What are the opportunity costs?

**3. Execution Feasibility (20%)**
- Do we have the capabilities?
- What resources are required?
- What is the realistic timeline?

**4. Risk Assessment (15%)**
- What could go wrong?
- What are mitigation strategies?
- Is the downside survivable?

**5. Timing Considerations (15%)**
- Why now vs later?
- What are market dynamics?
- Are there window constraints?

### Decision Thresholds

- **Score > 75**: Proceed with conviction
- **Score 55-75**: Proceed with safeguards
- **Score < 55**: Decline or revisit assumptions

## Board Management

### Meeting Preparation Checklist

**Three Weeks Before:**
- [ ] Draft preliminary financials
- [ ] Identify key discussion topics
- [ ] Flag items requiring board approval
- [ ] Schedule 1:1 calls with each director

**Two Weeks Before:**
- [ ] Finalize board package
- [ ] Distribute materials to directors
- [ ] Confirm attendance and logistics
- [ ] Prepare executive summary (1 page)

**Board Package Contents:**
1. Executive Summary with Key Asks
2. Financial Performance vs Plan
3. Operational KPIs Dashboard
4. Strategic Initiative Updates
5. Risk Register
6. Appendices (detailed backup)

### Effective Board Meetings

**Time Allocation:**
- Strategic Discussion: 50%
- Operational Review: 30%
- Administrative/Approvals: 20%

**Best Practices:**
- Lead with strategy, not operations
- Present recommendations, not just options
- Allow time for genuine discussion
- Capture action items with owners
- Follow up within 48 hours

## Investor Relations

### Fundraising Process

**Phase 1: Preparation (8-12 weeks)**
- Update financial model and projections
- Build comprehensive data room
- Develop pitch narrative and deck
- Research and tier target investors
- Prepare for common questions

**Phase 2: Marketing (4-6 weeks)**
- Initial outreach to warm contacts
- First meetings with Tier 1 firms
- Partner meetings with interested parties
- Reference calls facilitation

**Phase 3: Closing (4-6 weeks)**
- Term sheet negotiation
- Due diligence management
- Legal document review
- Closing mechanics

### Investor Update Template

```
Subject: [Company] Monthly Update - [Month Year]

HIGHLIGHTS
- [Key win #1]
- [Key win #2]
- [Key win #3]

METRICS
- Revenue: $X (+Y% MoM)
- Customers: X (+Y net new)
- Runway: X months

CHALLENGES
- [Challenge and what we're doing about it]

ASKS
- [Specific help needed from investors]

Next update: [Date]
```

## Crisis Management

### Response Protocol

**Hour 0-4: Assess**
- Gather verified facts
- Identify affected stakeholders
- Assess legal/regulatory implications
- Assemble response team

**Hour 4-12: Contain**
- Stop ongoing damage
- Secure evidence/documentation
- Brief board chair
- Engage external advisors if needed

**Hour 12-24: Communicate**
- Internal announcement to team
- Board notification
- External communication if required
- Regulatory filings if mandated

### Communication Principles

1. **Be Fast**: First mover shapes narrative
2. **Be Honest**: Never mislead stakeholders
3. **Be Complete**: Share what you know and don't know
4. **Be Accountable**: Own the problem
5. **Be Forward**: Focus on resolution

## Organizational Scaling

### Executive Hiring by Stage

**Seed Stage:**
- Focus: Technical co-founder, first engineer
- Profile: Builders who thrive in ambiguity
- Comp: Heavy equity, modest cash

**Series A:**
- Focus: VP Engineering, VP Sales
- Profile: Has built 10→50 person teams
- Comp: Market cash, meaningful equity

**Series B:**
- Focus: CFO, VP Marketing, VP People
- Profile: Has operated at 2-3x your current scale
- Comp: Competitive packages

**Series C+:**
- Focus: COO, General Counsel, CISO
- Profile: Enterprise experience, public company exposure
- Comp: Premium packages, retention focus

### Culture Definition

**Core Elements:**
- **Mission**: Why we exist
- **Vision**: Where we're going
- **Values**: How we operate (3-5 max)
- **Principles**: How we decide

**Value Definition Format:**
```
VALUE: [Name]
MEANING: [One sentence definition]
IN PRACTICE: [Observable behaviors]
NOT THIS: [Anti-patterns to avoid]
```

## Exit Planning

### IPO Readiness Checklist

- [ ] 3+ years audited financials
- [ ] SOX compliance program
- [ ] Independent board majority
- [ ] Public company-ready CFO
- [ ] Predictable revenue model
- [ ] Strong financial controls
- [ ] Clean cap table
- [ ] No material litigation

### M&A Preparation

- [ ] Continuously maintained data room
- [ ] Clean IP ownership
- [ ] Transferable customer contracts
- [ ] Key employee retention plans
- [ ] Tax structure optimization
- [ ] Known material issues documented

## Key Metrics to Track

### Leading Indicators
- Employee engagement/NPS
- Sales pipeline coverage
- Customer health scores
- Product velocity
- Cash burn rate

### Lagging Indicators
- Revenue vs plan
- Gross margin
- Net revenue retention
- Customer acquisition cost
- Employee turnover

## Common Scenarios

### Scenario: Difficult Board Conversation

When presenting bad news:
1. Lead with the headline - don't bury it
2. Own the situation - no blame shifting
3. Present root cause analysis
4. Share concrete remediation plan
5. Request specific support needed

### Scenario: Down Round

When raising at lower valuation:
1. Engage board early with scenarios
2. Explore alternatives (bridge, strategic)
3. Negotiate pay-to-play provisions carefully
4. Develop employee retention strategy
5. Control the narrative internally

### Scenario: Executive Departure

When a key executive leaves:
1. Understand true reasons (stay interview)
2. Negotiate departure terms
3. Plan transition and coverage
4. Communicate to team promptly
5. Begin search immediately

## Reference Materials

- `references/board_governance.md` - Board structure and fiduciary duties
- `references/fundraising_guide.md` - Comprehensive fundraising playbook
- `references/crisis_playbook.md` - Crisis response procedures
- `references/exit_planning.md` - IPO and M&A preparation

## Scripts

```bash
# Strategic position analysis
python scripts/strategy_analyzer.py --company "Name" --industry "Sector"

# Board meeting preparation
python scripts/board_prep.py --quarter Q1 --output board_pack/

# Investor deck generation
python scripts/investor_deck.py --stage "Series B" --metrics data.json

# Organizational health assessment
python scripts/org_health.py --survey results.csv
```