COO Advisor
Process design, OKR execution, operational cadence, and scaling playbooks.
$skillfish add ~skills/coo-advisor What This Skill Can Do
Concrete capabilities you get when you install this skill.
Design operational cadences: weekly rhythms, monthly reviews, quarterly planning
Build cross-functional processes that reduce handoff failures and delays
Implement OKR systems and operating frameworks across the company
Diagnose and fix operational bottlenecks slowing growth execution
Scale operations from 50 to 500 employees with repeatable processes
Manage multi-site, distributed, or international operations
Real Conversations
See how the COO Advisor skill responds to actual requests. These are representative examples of what your AI agent will produce.
We're growing from 32 to 60 people over the next 9 months. Every process we have was built for 15 people — Slack is chaos, no one knows who owns what, onboarding is broken. I'm the de facto COO/CEO. What do I prioritize first?
The 30→60 growth band is where most operationally chaotic startups either build the infrastructure or start losing talent and velocity. Here's the prioritization framework.
The three systems that break first at this scale (in order of urgency):
1. Decision-making clarity (fix in 30 days): At 32 people, you can tribal-knowledge your way through ownership questions. At 60, you can't. The minimum viable system: a RACI-lite document that answers, for every major function, "who decides, who executes, who is informed." This doesn't need to be complex — a Notion page with 20 rows covering hiring, product priorities, pricing, technical decisions, and vendor contracts is enough. The act of writing it surfaces 80% of the ownership ambiguity.
2. Onboarding infrastructure (fix in 45 days): Broken onboarding compounds — every bad hire experience spreads through the org. Build a role-specific 30-60-90 day plan template, an onboarding wiki with company context, and assign an onboarding buddy (not a manager) for every new hire's first 30 days. This is a 2-week project for one person to build once.
3. Operating cadence (fix in 60 days): Chaos in Slack is a symptom of no structured communication rhythm. Implement: weekly leadership team sync (60 min, standard agenda), biweekly all-hands (30 min, wins + focus), monthly written update from you to the company. Channels get specific purposes — #ops-decisions, #engineering-decisions, etc. Noise goes to #random.
What I'd deprioritize: OKR systems, advanced project management tools, formal org charts. These matter at 100 people. Right now you need decision clarity and communication structure, not process sophistication.
The hire you need by month 6: A Chief of Staff or VP of Operations. Not a senior operations manager — someone who thinks in systems and can own the operational build while you run the company.
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
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Context Window
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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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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 COO Advisor?
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$skillfish add ~skills/coo-advisor