C-Level Advisory OrchestrationC-SuiteRouting

Chief of Staff

C-suite orchestration layer for routing questions to the right advisor.

$skillfish add ~skills/chief-of-staff

Capabilities Real Examples Get Started Models & Context

What This Skill Can Do

Concrete capabilities you get when you install this skill.

Build and run executive operating cadences (weekly, monthly, quarterly)

Coordinate cross-functional strategic initiatives and track executive commitments

Prepare board materials, investor updates, and executive communications

Route and triage C-suite decisions to the right owner at the right time

Run special projects that don't fit within existing functional ownership

Design decision-making frameworks and escalation paths for the leadership team

Real Conversations

See how the Chief of Staff skill responds to actual requests. These are representative examples of what your AI agent will produce.

You

We're thinking about moving from per-seat to usage-based pricing. I want to know: (1) whether this will hurt our current ARR, (2) what the competitive landscape for UBP looks like in our category, and (3) how to structure the transition for existing customers. Route me to the right advisors.

Agent

This question spans three distinct domains. Here's how I'd route it.

Question 1 — Impact on current ARR: This is a CFO Advisor question with a CRO Advisor overlay. The CFO models the revenue impact of the transition (expected ARR change, churn risk from pricing change, revenue recognition implications). The CRO models customer behavior under new pricing and the risk to net revenue retention. Start with CFO Advisor to build the financial model, then validate assumptions with CRO Advisor on customer response.

Question 2 — Competitive landscape for UBP: This is a CMO Advisor + CPO Advisor question. CMO can do a competitive positioning analysis on how category leaders are pricing. CPO should weigh in on whether your product has the right usage metrics to serve as billing dimensions — not all products translate well to UBP.

Question 3 — Transition structure for existing customers: This is primarily CRO Advisor territory — customer communication, renewal conversion, handling objections on pricing change — with CFO Advisor input on grandfathering economics and the timing of the transition relative to your revenue recognition.

Suggested sequence:

Start with CPO Advisor: Define the usage metric candidates and confirm the product is architected to track them accurately.
Move to CFO Advisor: Model 3 scenarios (no transition, immediate transition, 12-month gradual transition) on current ARR base.
Close with CRO Advisor: Build the customer communication and sales playbook.

Should I set up the context document for this project so each advisor works from the same baseline company data?

You

Something is wrong but I can't name it. Growth was 14% MoM 6 months ago, now 5%. Team is working hard but we feel like we're running in place. No single obvious cause. Sales says product, product says sales is targeting wrong customers, engineering says both teams keep changing priorities. I need a cross-functional diagnosis.

Agent

The symptom pattern you're describing — growth deceleration without a single obvious cause, cross-functional blame, and high effort with low output — is a classic strategic drift signal. It requires a structured cross-functional diagnostic, not just one advisor.

Here's how I'd orchestrate this:

First, run CEO Advisor on strategic drift diagnosis. The cross-functional blame pattern (sales ↔ product ↔ engineering) almost always has a strategic root: either your ICP has shifted without your GTM model following, or your product-market fit is narrower than you're selling into. CEO Advisor will help you distinguish between an execution problem and a strategy problem.

In parallel, run CRO Advisor on a pipeline quality audit. "Sales targeting wrong customers" is a testable hypothesis. Examine win rates by segment, deal size, and lead source over the last 6 months vs. prior period. If win rates are stable but pipeline volume dropped, the problem is top-of-funnel. If win rates dropped, it's either product-market fit or sales execution.

Then run CPO Advisor on roadmap volatility. "Engineering says both teams keep changing priorities" is a product management system failure. The CPO diagnostic will assess whether you have a stable roadmap commitment framework or whether the team is reacting to every sales request and every customer complaint.

The synthesis I'd recommend: After running each diagnostic separately, bring findings to a Board Meeting session (the multi-advisor protocol) where CEO, CRO, and CPO views are integrated into a single diagnosis. Drift problems almost always look different from each functional vantage point — the real cause lives in the intersection.

What I'll do: Flag that this conversation should reference the same company context document. Do you have a Context Engine loaded, or should we start by capturing the baseline metrics?

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

Best

Claude Opus 4 Claude Sonnet 4 GPT-4.1 Gemini 2.5 Pro Grok 3 Kimi K2

Good

Claude Haiku 4.5 GPT-4.1 mini Gemini 2.5 Flash Grok 3 mini

Larger models produce more detailed, production-ready outputs.

Context Window

This skill's SKILL.md is typically 3–10 KB — fits in any modern context window.

8K Skill only

32K+ Skill + conversation

100K+ Skill + references + codebase

All current frontier models (Claude, GPT, Gemini) support 100K+ context. Use the full window for complex multi-service work.

Pro tips for best results

1

Be specific

Include numbers — users, budget, RPS — so the skill can size the architecture.

2

Share constraints

Compliance needs, team size, and existing stack all improve the output.

3

Iterate

Start with a high-level design, then ask follow-ups for IaC, cost analysis, or security review.

4

Combine skills

Pair with companion skills below for end-to-end coverage.

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