Chief Strategy Officer
A CSO persona skill that frames multi-year choices: where to play, build vs. buy vs. partner, and what you're giving up.
What it does
Puts Claude in the seat of a Chief Strategy Officer, reasoning on a multi-year horizon instead of the current quarter.
- Where to play: which markets, segments, and businesses to enter or exit
- Corporate development: acquisitions, divestitures, and diligence
- Capital allocation across business lines
- Planning under uncertainty: scenarios, assumptions, early-warning indicators
Two sharp tests drive every answer: (1) What does this strategy say no to? — a strategy with no sacrifice is "a budget with adjectives." (2) Could a competitor say the same sentence? — if so, it's positioning boilerplate.
Output always follows a six-part return contract: the choice, why now, what we give up, the assumptions, what would falsify it, and the first commitment with a date.
Who it's for
- Founders and BD leads weighing market entry or exit
- Strategy/corp-dev people who need a written deal thesis before an approach
- Executives justifying capital allocation across business units
- Anyone stress-testing board decks or consulting proposals for logical rigor
Examples
- "Should we enter Japan directly or via a reseller partner?" → a six-part answer with the choice, the sacrifice, key assumptions, and falsifying indicators.
- "Competitor A is up for sale." → the skill first asks whether a deal thesis existed beforehand and flags buying because something is merely available.
- "Here's next year's strategy draft." → it separates goals ("grow 40%") from actual choices and calls out lines any competitor could say.
· · · 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)
- Download the ZIP with the button below.
- In Claude, open Settings → Capabilities and turn on 'Code execution and file creation'. (one time)
- Go to Customize → Skills → + → 'Upload a skill' and upload the 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.
- Open Terminal (macOS/Linux) or Git Bash (Windows).
- Clone the repo:
git clone https://github.com/cbrock84/headcount.git - Create the skills directory:
mkdir -p ~/.claude/skills - Copy just this skill:
cp -r headcount/plugins/corporate-strategy/skills/chief-strategy-officer ~/.claude/skills/ - Restart Claude Code and confirm
chief-strategy-officerappears in your skill list. - Trigger it with prompts like "As CSO, should we enter this market?" or "build, buy, or partner here?"