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Portfolio Strategy Agent Skill

Decides where capital and attention go across business lines, products, and markets — what to fund, hold, harvest, or exit, and on what evidence. Use this to allocate budget across businesses, evaluate whether a product line should continue, decide market entry or exit, structure a portfolio review, or when several initiatives compete for the same limited investment.

767 tokens
context cost
the whole folder, loaded on every use
1
files
instructions only
0
copies elsewhere
how many repositories repackaged it
220
stars on the repo
on the repository, not the skill itself

Install

one command, takes just this skill from the repository
npx skills add https://github.com/cbrock84/headcount --skill portfolio-strategy

The instruction itself

6 sections, as written by the author

Portfolio strategy

Most organizations fund by inertia. Last year's allocation plus a percentage, adjusted by who argued

hardest. Portfolio strategy is the discipline of deciding again, deliberately.

Assess each line on two axes

Attractiveness — is this a good place to be? Market size and growth, structural profitability,

concentration of buyer power, regulatory direction, and how the economics behave as it scales.

Right to win — is it good *for us*? Our position relative to alternatives, the assets or

capabilities that transfer, and whether the advantage is durable or borrowed.

The combination gives you four postures, and the honest one is usually uncomfortable:

  • Attractive, we can win — fund properly. Underfunding these is the most common and most

expensive portfolio error.

  • Attractive, we cannot win — the seductive trap. Everyone wants in on a good market. Entering

without an advantage funds someone else's growth.

  • Unattractive, we can win — harvest. Run for cash, do not invest for growth.
  • Neither — exit. Slowly and reluctantly is how these consume a decade of attention.

Judge on marginal return, not absolute size

The question is never "is this business good." It is "what does the next dollar do here versus

elsewhere." A large profitable line may be a poor place for incremental investment; a small one may

be the best.

Watch for cross-subsidy. A weak line supported by a strong one is a decision, and it should be

an explicit one with a thesis and an end date — not an accident nobody has looked at.

Exit is the hardest decision and the most valuable

Sunk cost, internal advocates, and the discomfort of admitting a bet failed all argue for one more

year. The test is prospective: knowing what we know now, would we start this today? If not, the

only question is how to exit well.

Exiting frees more than the money. It frees the attention of the people running it, which is usually

the scarcer resource.

Plan exits properly: customer commitments, employee treatment, and contractual obligations. A badly

run exit costs more than the business was losing.

Running a review

Same evidence for every line, prepared by a neutral party rather than by each line's advocate. Set

the criteria and weights before seeing the numbers — weighting afterward reproduces the

allocation you already had.

Force a ranking. Tiers are how everything stays funded.

Return contract

Each line with its posture and evidence, the recommended allocation and what changed from last

period, what you are stopping, and the indicator that would reverse each call.

How to use it

Copy the folder

Take cbrock84/portfolio-strategy from the repository into ~/.claude/skills for personal use, or into .claude/skills inside a project.

Check the name does not clash

The agent identifies a skill by the name field in its header. Two skills with the same name cannot sit side by side — one of them will be ignored.