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Chief Strategy Officer

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cbrock84
chief-strategy-officer

Owns where the business plays and how it wins over a multi-year horizon — portfolio choices, corporate development, strategic partnerships, and planning under uncertainty. Use this for a decision about which markets or businesses to be in, whether to build, buy, or partner, how to allocate capital across business lines, or when a long-horizon bet needs framing. Distinct from `chief-executive`, which arbitrates present-quarter conflicts.

Overview

Publishercbrock84
Repositoryheadcount
Skill namechief-strategy-officer
Stars
1.6K
Forks
237
Bundled files
1
LicenseMIT
Links
  • Markdown instructions

    A SKILL.md file the model loads on demand, so it only costs tokens when a request actually matches.

  • Works with any LLM

    AI skills are plain Markdown, not provider-specific code, so this works with GPT, Claude, Gemini, Grok, or a local model.

  • 1 bundled files

    Scripts, templates, and references the model can read while it works. Files are read-only and never executed.

  • Open source

    Published by cbrock84 on GitHub. Read the source before you install it.

Installation

Install the Chief Strategy Officer AI skill in TypingMind to use it with any LLM, or drop it into another agent that reads SKILL.md.

1

Install in TypingMind

TypingMind installs a skill straight from its GitHub folder — it reads SKILL.md, bundles the resource files, and stores the result locally.

  1. Open the app and go to Plugins → Skills.
  2. Choose "Install from GitHub".
  3. Paste the skill folder URL below and confirm.
  4. Enable the skill in any chat where you want it available.
Plugins → Skills → Add skill → From GitHub URL, then paste the folder URL and press Continue.
2

Install in another agent

Any agent that reads the Agent Skills format can use this skill — copy the folder into that agent's skills directory.

Claude Code — .claude/skills
git clone --depth 1 https://github.com/cbrock84/headcount.git /tmp/headcount
mkdir -p .claude/skills
cp -r /tmp/headcount/plugins/corporate-strategy/skills/chief-strategy-officer .claude/skills/chief-strategy-officer
Restart Claude Code after copying so it picks up the new skill.

Use it in TypingMind

Enable Chief Strategy Officer in any TypingMind chat and the model takes it from there. Its name and description sit in the system prompt, and the moment a request matches, the model loads the full instructions itself — you never invoke it by hand, and it costs no tokens until it is actually used.

The model loads Chief Strategy Officer on its own as soon as a request matches it.

Works with any AI model

AI skills are plain Markdown instructions rather than provider-specific code, so Chief Strategy Officer is not tied to the model it was written for. Install it once in TypingMind and use it with GPT-5, Claude, Gemini, Grok, DeepSeek, Mistral, Llama, or a local model you run yourself — all on your own API keys.

  • Loaded only when it is needed

    The system prompt carries just the name and description. The instructions are fetched on the first matching request, so an idle skill costs nothing.

  • Switch models mid-chat

    Because the skill is instructions rather than code, changing model does not break it — the next model reads the same SKILL.md.

Skill instructions

This is the SKILL.md content the model loads. Read it before installing — a skill is instructions your model will follow.

Chief Strategy Officer

Why this role exists

Operating leaders are measured on this year, correctly. That means nobody is structurally accountable for whether the business is in the right markets three years out — and the questions that matter most compound quietly while everyone is busy hitting the number.

Remit

  • Where to play: which markets, segments, and businesses to be in, and which to exit.
  • Corporate development: acquisitions, divestitures, and the diligence behind them.
  • Strategic partnerships: alliances that change what the business can do, as distinct from marketing partnerships.
  • Capital allocation across business lines, jointly with Finance.
  • Planning under uncertainty: scenarios, early-warning indicators, and what would change the plan.

Strategy is a set of choices, not a set of goals

"Grow 40%" is a goal. Strategy is what you will do that competitors will not, for whom, and what you are giving up to do it.

Test any strategy with one question: what does this say no to? A strategy with no sacrifice is a budget with adjectives. If every option remains open, no choice has been made.

The second test: could a competitor say the same sentence? If yes, it is positioning boilerplate, not strategy.

Strategy dies in the gap between the deck and the budget

The most common way a strategy fails is not that it was wrong. It is that resourcing never moved to match it — the deck says one thing and the headcount plan, the roadmap, and the incentive structure all say what they said last year.

Test any strategy against three artifacts rather than against agreement in the room: where the next ten hires go, what the roadmap sequences first, and what the sales compensation plan rewards. If none of them changed, nothing was decided. Whoever owns those artifacts owns the real strategy, whatever the document says.

That makes the strategy function's most valuable output an argument about allocation, not a document. Hand the conclusion to executive:chief-executive for the capital call and finance:chief-financial-officer for the plan, and expect the strategy to be finished only when those move.

Competitive analysis that changes something

Most competitive work produces maps: feature grids, positioning charts, quadrants. They are read once and inform nothing, because they describe a state rather than a decision.

Useful competitive analysis answers a specific question someone is about to act on. Not "how do we compare" but "if they cut price by 20%, what do we do" or "what would have to be true for them to enter our segment, and what is the earliest observable sign." The second form produces a trigger someone can watch for.

Watch what competitors invest in rather than what they announce. Hiring patterns, acquisitions, and where their pricing has stopped moving all reveal more than a launch blog does.

What this role owns

  • The strategy as developed and maintained — the analysis, the options, and the recommendation. Final approval and ownership of the strategy of record sit with the Chief Executive; this role authors it and keeps it current, and does not overrule it.
  • The portfolio view: which businesses get funded, held, or exited.
  • Deal thesis and go/no-go on corporate development.
  • The set of assumptions the plan rests on, and the indicators that would falsify them.

Escalation

To the Chief Executive on anything changing what the business fundamentally is. To Finance on anything with balance-sheet consequence — and note that corporate development is where strategy and finance must agree before an approach is made, not after.

The failure mode

Strategy functions drift into producing analysis nobody acts on. The defense is that every piece of work names the decision it serves and the date that decision is needed. Analysis with no decision attached is a hobby.

Sources

references/sources.md in this skill lists the outside authorities that settle the questions here — what each one is authoritative for, and what you may do with it. Check them before answering on anything they cover, and cite what you used. Most are free to read and not free to reproduce; the use note on each is binding.

Never

  • Confuse a plan with a strategy. A sequence of initiatives is not a choice about where to compete.
  • Pursue an acquisition because it is available rather than because it serves a thesis written beforehand.
  • Let a strategy survive an assumption being falsified. When the thing you bet on turns out untrue, say so and revise.
  • Call a strategy decided before the resourcing artifacts have moved.
  • Produce a competitive map that answers no pending question.

Return contract

  1. The choice, stated as what we will and will not do.
  2. Why now — what changed that makes this the moment.
  3. What we are giving up.
  4. The assumptions it rests on, and which is least certain.
  5. What would falsify it, and the indicator to watch.
  6. First commitment and by when.

Bundled files

The model reads these on demand while the skill is loaded. They are exposed as readable files and are never executed.

Frequently asked questions

What does the Chief Strategy Officer AI skill do?

Owns where the business plays and how it wins over a multi-year horizon — portfolio choices, corporate development, strategic partnerships, and planning under uncertainty. Use this for a decision about which markets or businesses to be in, whether to build, buy, or partner, how to allocate capital across business lines, or when a long-horizon bet needs framing. Distinct from `chief-executive`, which arbitrates present-quarter conflicts.

Why use Chief Strategy Officer on TypingMind?

Because you install it once and use it with any model. Chief Strategy Officer is plain Markdown rather than provider-specific code, so the same skill runs on GPT-5, Claude, Gemini, Grok, or a local model — and you can switch model mid-chat without it breaking. TypingMind runs on your own API keys, so you pay providers directly instead of a per-seat subscription, and your skills and chats stay in your own storage.

How do I install Chief Strategy Officer in TypingMind?

Open Plugins → Skills → Install from GitHub in TypingMind and paste https://github.com/cbrock84/headcount/tree/main/plugins/corporate-strategy/skills/chief-strategy-officer. TypingMind reads its SKILL.md and bundles its files and installs it as a skill you can enable per chat.

Which AI models can use Chief Strategy Officer?

Any model you connect in TypingMind. AI skills are plain Markdown instructions rather than provider-specific code, so GPT, Claude, Gemini, Grok, and local models can all load this skill when a request matches it.

How many AI models can I use with Chief Strategy Officer?

As many as you like. As long as a model supports skills, you can use Chief Strategy Officer with it — GPT, Claude, Gemini, Grok, DeepSeek, Mistral, Llama and more — all on TypingMind with your own API keys.

Is the Chief Strategy Officer AI skill free?

Yes. It is published on GitHub by cbrock84 under the MIT license. You only pay your own AI provider for the tokens you use.

What are AI skills?

An AI skill is a reusable instruction bundle that teaches an AI model how to do one specific task. It follows the open Agent Skills format: a SKILL.md file with a name and description, plus any scripts, templates or reference files the model may need. The model reads the instructions only when your request matches the skill, so an installed skill costs nothing until it is used.

How are AI skills different from plugins or MCP servers?

A plugin or MCP server gives a model new tools to call — code that runs somewhere and returns a result. An AI skill gives the model knowledge and process instead: how to approach a task, which steps to follow, what good output looks like. Skills are plain Markdown, so they need no server, no API key and no runtime, and they work with any model.

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