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Chief Strategy Officer

A CSO persona skill for multi-year decisions: where to play, build vs. buy vs. partner, portfolio and capital allocation, and planning under uncertainty.

Docs & OfficeIntermediate★ 2,032⑂ 316AI score 8/10Last updated: Sep 17, 2026

What it does

  • Reframes strategy as a set of choices, not goals. Stress-tests any draft with "what does this say no to?" and "could a competitor say the same sentence?"
  • Where to play: which markets, segments, and business lines to fund, hold, or exit.
  • Build / buy / partner: deal thesis first, diligence angles, and a go/no-go recommendation.
  • Resourcing reality check: a strategy counts as decided only when the next ten hires, the roadmap sequence, and the sales comp plan actually change.
  • Planning under uncertainty: scenarios, the assumptions the plan rests on, and the early-warning indicator that would falsify each one.
  • Every answer lands in a fixed contract: the choice, why now, what we give up, assumptions, falsifiers, and the first commitment with a date.

Who it's for

  • Founders, executives, corporate strategy and biz-dev teams
  • Teams weighing a new market entry or an exit
  • Anyone evaluating an inbound acquisition or partnership offer
  • Orgs whose competitive analysis gets read once and changes nothing

Examples

  1. "Should we expand into the enterprise segment next year? Spell out what we give up and what would falsify the bet."
  2. "Build payments in-house, acquire a small PSP, or partner? Write the deal thesis first."
  3. "If a competitor cuts price 20%, what do we do — and what's the earliest observable signal to watch?"

· · · Install guide · · ·

Try it now, no install

Paste this into Claude to use the skill without installing anything.

Read the instructions in this file and follow them to help me:
https://raw.githubusercontent.com/cbrock84/headcount/HEAD/plugins/corporate-strategy/skills/chief-strategy-officer/SKILL.md

What I want: (describe your task here)

If Claude can't open the link, open it yourself and paste the contents instead.

↓ If it works for you, download the ZIP below and install it. Then it runs on its own — no pasting each time.

Install in the Claude app (no terminal)
  1. Download the ZIP with the button below.
  2. In Claude, open Settings → Capabilities and turn on 'Code execution and file creation'. (one time)
  3. Go to Customize → Skills → + → 'Upload a skill' and upload the ZIP.
↓ Download ZIP
Install in Claude Code

Let Claude do it — paste this into Claude Code

Install the skill I found on Claude Skill Mart.
Copy the plugins/corporate-strategy/skills/chief-strategy-officer folder from the GitHub repo cbrock84/headcount into my ~/.claude/skills/chief-strategy-officer/.
When it's done, tell me in one line what this skill can do.

Install with a command instead

git clone https://github.com/cbrock84/headcount.git && mkdir -p ~/.claude/skills && cp -r headcount/plugins/corporate-strategy/skills/chief-strategy-officer ~/.claude/skills/

⚠ This is a third-party skill. Check the source repository before installing.

  1. Open a terminal.
  2. Clone the repo: git clone https://github.com/cbrock84/headcount.git
  3. Create the skills folder: mkdir -p ~/.claude/skills
  4. Copy the skill: cp -r headcount/plugins/corporate-strategy/skills/chief-strategy-officer ~/.claude/skills/
  5. Confirm references/sources.md came along — the skill cites it for outside authorities.
  6. Restart Claude Code and ask something like "Help me decide which markets we should be in three years out."
View source on GitHub ↗License: MIT