C-Level Advisory OnboardingSetupContext

CS Onboard

Founder onboarding interview capturing company context across 7 dimensions.

$skillfish add ~skills/cs-onboard

Real Conversations

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

You

I just installed the C-suite advisor package. Where do I start? We're a 3-year-old B2B SaaS company, $3.1M ARR, 41 employees, just closed a Series A for $9M. Building HR compliance software for companies in financial services and healthcare. How do I set up the context so all advisors can use it?

Agent

Welcome — let's build your company context document in this session. I'll ask questions across 7 dimensions and compile a structured profile all C-suite advisors can load.

What I already have from your message:

  • Product: HR compliance software
  • Verticals: Financial services and healthcare
  • Stage: Series A, $9M raised
  • ARR: $3.1M
  • Headcount: 41
  • Founded: ~3 years ago

7 dimensions to complete — let me ask:

1. Unit economics: What's your average ACV? Approximate NRR? Gross margin %?

2. GTM motion: Inbound-led, outbound-led, or PLG? Who's your typical buyer (title and company size)?

3. Runway: With $9M raised and current burn, approximately how many months of runway?

4. Top 3 priorities this quarter: What are you trying to prove or build in the next 90 days?

5. Biggest risks: What keeps you up at night — market, product, team, or competition?

6. Leadership team: Key roles filled and any critical gaps you're hiring for?

7. Active decisions: What are you currently deciding that an advisor could help with?

Once I have these answers, I'll compile your context document in a format you can paste at the start of any advisor session.

Why this matters: A CEO advisor with full context gives you specific, calibrated advice. Without it, you get generic frameworks. What are your approximate ACV and NRR numbers?

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.

Ready to try CS Onboard?

Install the skill and start getting expert-level guidance in your workflow — any agent, any IDE.

$skillfish add ~skills/cs-onboard
← Browse all 169 skills