Skills

Chief Strategy Officer

Owns where the business plays and how it wins over a multi-year horizon, portfolio...

Install

npx skills add cbrock84/headcount --skill chief-strategy-officer -g -a claude-code -y
Repository
cbrock84/headcount2.6k
Category
Business
Updated
17d ago
License
MIT
Context cost
Lightabout 1,260 tokens
Runs scripts
No, instructions only

What it does

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.

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.

Read the whole SKILL.md on GitHub

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