CEO Advisor
Executive leadership guidance for strategic decision-making and stakeholder management.
$skillfish add ~skills/ceo-advisor What This Skill Can Do
Concrete capabilities you get when you install this skill.
Design fundraising strategy and investor narrative from Seed through Series C
Navigate co-founder conflict, equity disputes, and executive departures
Structure board composition, governance, and investor relations
Plan strategic pivots with board alignment and stakeholder communication
Optimize executive org structure and C-suite hiring for growth stage
Prepare for M&A — as acquirer, acquisition target, or merger partner
Real Conversations
See how the CEO Advisor skill responds to actual requests. These are representative examples of what your AI agent will produce.
We're at $2.4M ARR, growing 15% MoM but burn is $210K/month. We have 11 months runway. Board is split — half want me to raise a Series B now while momentum is there, the other half want me to cut to default alive first. I'm 45 days from closing a $400K enterprise deal that would change our unit economics. What's the move?
This is a leverage timing problem, not a binary raise-vs-cut question. Let me work through it.
Your actual position: At 15% MoM, you're doubling roughly every 5 months. That's Series B-fundable growth. But 11 months runway means you'd be raising from a position of moderate pressure — investors will sense it.
The $400K deal changes everything if it closes. Here's how I'd think about it:
- Do not cut aggressively in the next 45 days. Cutting now signals distress, disrupts the team closing that deal, and doesn't meaningfully extend runway (45 days of cuts = maybe 2 weeks extra runway).
- Run a soft process in parallel. Take 3–4 warm intro meetings with B-stage investors now. Don't pitch — just reconnect. If the deal closes, you re-enter those conversations with a very different story: $2.8M ARR, enterprise validation, improving unit economics.
- Model two scenarios explicitly for the board: (a) Deal closes → raise at $12–15M valuation on strong metrics; (b) Deal slips → implement 20% burn reduction to 14-month runway, then raise.
What I'd push back on: The "cut to default alive" camp is right philosophically but wrong on timing. Default alive at $2.4M ARR with 15% MoM growth means cutting to ~$80K burn — that likely means losing the sales capacity closing the enterprise deal. You'd be optimizing for survival at the cost of the catalyst that changes your fundraise.
Bottom line: Conditional raise strategy. 45-day deadline, soft process running, explicit board alignment on which scenario triggers which action.
Get Started
How to install and use this skill in your preferred environment.
Skills are designed for AI coding agents (Claude Code, Cursor, Windsurf) and IDE-based workflows where the agent can read files, run scripts, and act on your codebase. Web-based AI can use the knowledge and frameworks, but won't have tool access.
Models & Context
Which AI models and context windows work best with this skill.
Recommended Models
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Context Window
This skill's SKILL.md is typically 3–10 KB — fits in any modern context window.
All current frontier models (Claude, GPT, Gemini) support 100K+ context. Use the full window for complex multi-service work.
Pro tips for best results
Be specific
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Share constraints
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Iterate
Start with a high-level design, then ask follow-ups for IaC, cost analysis, or security review.
Combine skills
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Ready to try CEO Advisor?
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$skillfish add ~skills/ceo-advisor