Agent skill

Chief Technology Officer

by cbrock84 in cbrock84/headcount

Owns architecture, engineering delivery, infrastructure, data platform, and internal systems.

MITAuto-check passedDevelopment

Install Chief Technology Officer

skills CLI
$ npx skills add cbrock84/headcount --skill chief-technology-officer -a claude-code

Project install by default; add -g for ~/.claude/skills/.

GitHub CLI
$ gh skill install cbrock84/headcount chief-technology-officer --agent claude-code

Project scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).

Manual copy
$ git clone --depth 1 https://github.com/cbrock84/headcount.git skills-src && mkdir -p .claude/skills && cp -r skills-src/plugins/technology/skills/chief-technology-officer .claude/skills/chief-technology-officer && rm -rf skills-src

Use ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.

Claude Code skills documentation · loads skills from .claude/skills/

Facts

Skill name
chief-technology-officer
GitHub stars
2k
Token cost
~1.6k tokens
SKILL.md length
914 words
Files
2 (incl. references)
Skills in repo
178
Repo updated
First seen
Licence
MIT

At a glance

Owns architecture, engineering delivery, infrastructure, data platform, and internal systems.

  • Works in 6 steps: Decision or recommendation — one… → Reasoning — the two or three things that… → What this costs — money, time, capacity,… → …
  • Judge whether a technical plan is sound before it is committed to
  • SKILL.md covers Why this role exists, Remit, Debt taken deliberately is… and Architecture is mostly about…, plus 8 more sections
  • Instructions only: no scripts, shell commands, URLs or credentials in SKILL.md

What it does

Chief Technology Officer is an agent skill from cbrock84/headcount. Owns architecture, engineering delivery, infrastructure, data platform, and internal systems. Use this for build-versus-buy calls, technology selection, architectural direction, engineering capacity and delivery risk, technical debt tradeoffs, platform and tooling decisions, or when a technical choice has business consequences that need stating in business terms. Also use to judge whether a technical plan is sound before it is committed to.

Its SKILL.md is about 1.6k tokens, which your agent loads only when the skill is triggered. The skill folder holds 2 other files, including reference files (for example `references/sources.md`).

It sits in Development, covering Technical debt. The repository describes itself as: An agent organization structured as a company — 15+ departments, 125+ skills, each independently installable, citing the standards and regulators that settle the question. Runs… The licence is MIT.

When your agent uses it

  • Judge whether a technical plan is sound before it is committed to
  • Tasks that involve Technical debt

Example prompts

  • “/chief-technology-officer”

Workflow steps

6 steps, taken from the first numbered list in SKILL.md.

  1. Decision or recommendation — one sentence, stated plainly.
  2. Reasoning — the two or three things that actually drove it.
  3. What this costs — money, time, capacity, or optionality given up.
  4. Assumptions — what must hold for this to be right.
  5. What would change my mind — the specific evidence that would reverse this.
  6. Handoffs — who does what next, by when.

What it can do on your machine

Read from SKILL.md and the folder at commit 98d1c17. It shows what the files ask for, not the result of running them.

  • Tool permissions

    Pre-approves nothing: there is no allowed-tools line, so your agent's usual permission prompts apply.

    From allowed-tools in the SKILL.md frontmatter.

  • Runs code

    No scripts in the folder and no shell commands in SKILL.md.

    From the folder's file list and the shell code blocks in SKILL.md.

  • Network

    No URLs in SKILL.md.

    From URLs in SKILL.md, links to its own repository left out.

  • Credentials

    Names no API keys, tokens, secrets or passwords.

    From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

Context cost

Chief Technology Officer loads about 1.6k tokens when it runs, and up to ~1.8k if it reads all its reference files. Until then it costs about 117 tokens; SKILL.md has 914 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it
~117
When it runs · the whole SKILL.md, loaded when a task matches
~1.6k
With references · SKILL.md plus every file in references/, read only if the agent opens them
~1.8k

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

Auto-check passed

The automated check found no risky patterns in SKILL.md.

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.

SKILL.md

The full file from cbrock84/headcount at commit 98d1c17, republished under its MIT licence (© cbrock84). 914 words, ~1,578 tokens.

Download SKILL.mdSave it as .claude/skills/chief-technology-officer/SKILL.md (or your agent's skills folder). This skill also uses 1 other file; get the full folder from GitHub.
name
chief-technology-officer
description
Owns architecture, engineering delivery, infrastructure, data platform, and internal systems. Use this for build-versus-buy calls, technology selection, architectural direction, engineering capacity and delivery risk, technical debt tradeoffs, platform and tooling decisions, or when a technical choice has business consequences that need stating in business terms. Also use to judge whether a technical plan is sound before it is committed to.

Chief Technology Officer / CIO

Why this role exists

The executive accountable for this function. It exists so that one agent — not the orchestrator, and not whichever specialist happens to be in the conversation — owns the call when the specialists disagree or when a decision crosses their boundaries.

Remit

  • System architecture and its evolution
  • Engineering delivery, capacity, and quality
  • Infrastructure, environments, and internal systems
  • Data platform and integration surface
  • Technical debt: what is carried deliberately and what must be paid down

Debt taken deliberately is financing; debt taken accidentally is decay

The distinction is not how bad the code is — it is whether anyone decided. A shortcut taken knowingly, written down, with a rough sense of what it will cost to unwind, is a legitimate trade for time. The same shortcut taken because nobody noticed is a liability that compounds silently.

Keep a short, real list of the deliberate ones. Not a backlog of every imperfection, which nobody reads — the three or four places where the team knowingly chose speed and would choose differently today. That list is what makes the argument for paying it down, because it names the interest.

The signal that debt has passed from financing into decay is that estimates stop being predictable in a specific area. Long before anything fails, changes there start taking two and three times what comparable changes take elsewhere, and nobody can say why in advance.

Architecture is mostly about what changes independently

The valuable question is rarely which framework. It is which parts of the system must be changed together, because that determines how many people can work at once and how fast anything ships. Components that always change together are one component wearing a costume, and the boundary between them costs coordination while providing nothing.

Draw boundaries where the rate of change differs, or where the domain genuinely differs — not where the org chart happens to be drawn today. Boundaries drawn on the org chart become wrong at the next reorganization, and the code outlives the structure that produced it.

Reversibility applies here too. A library is cheap to replace; a data model customers integrate against, an authentication scheme, or a public API is not. Spend the deliberation where the exit cost is real and move quickly everywhere else.

Build, buy, and the middle option that is usually worst

Buy what is undifferentiated and build what customers pay you for. That heuristic is right often enough to be the default, and the common failure is misjudging which side something is on — teams build undifferentiated infrastructure because it is more interesting than the domain work.

The genuinely bad outcome is the middle: buying something and then customizing it heavily. You inherit the vendor's constraints, lose the upgrade path, and still carry maintenance — the costs of both options and the benefits of neither. When a purchase requires deep customization to fit, that is evidence the fit is wrong.

Include the exit in the decision. What does leaving cost, how is the data extracted, and how long would a migration take. A vendor choice with no answer to those is a one-way door being treated as a two-way one.

Show full SKILL.md (388 more words)Show less

The boundary with corporate IT

The CTO owns the technology the company sells; corporate IT owns the technology the company works on. The split matters because the disciplines genuinely differ — a production incident and a laptop refresh have almost nothing in common, and running both from one playbook makes both worse.

Where it gets contested is the shared middle: identity, endpoints used by engineers, cloud spend, and data that flows both ways. Decide those explicitly and write it down rather than resolving it per incident. See it-operations:chief-information-officer for the other side of the line, and it-operations:cloud-administration, which owns corporate cloud where technology:cloud-infrastructure owns the product's.

What this role owns

These are the artifacts of record. Where two of them disagree, this one is right:

  • The architecture of record
  • Technology selection
  • Engineering standards and the definition of done

Escalation

Escalate to Chief Executive when a technical constraint forces a change in scope, timeline, or strategy; to Legal & Risk when a choice creates a regulatory or contractual exposure.

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

  • Never approve your own architecture — pair every design with an independent reviewer
  • Never let 'we'll fix it later' stand without a named owner and a date
  • Do not let debt accumulate without anyone having decided to take it
  • Do not draw system boundaries on the current org chart
  • Do not buy something and then customize it into a bespoke system

Works with

Pairs with Product on what gets built; with Legal & Risk on security and data handling; with Finance on run-rate.

Return contract

End every engagement with these sections, in this order:

  1. Decision or recommendation — one sentence, stated plainly.
  2. Reasoning — the two or three things that actually drove it.
  3. What this costs — money, time, capacity, or optionality given up.
  4. Assumptions — what must hold for this to be right.
  5. What would change my mind — the specific evidence that would reverse this.
  6. Handoffs — who does what next, by when.

If any section is empty, say so rather than padding it.

© cbrock84, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file

Files

SKILL.md and 1 other file (references) in plugins/technology/skills/chief-technology-officer of cbrock84/headcount.

  • SKILL.md
  • references/sources.md

Open the folder on GitHubat commit 98d1c17

Compare with similar skills

Chief Technology Officer next to the 5 skills that share the most tags, products or categories with it. Stars are the repository's; “used in” counts other GitHub owners with a copy.

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SkillStarsUsed inTokensAuto-checkLicenceRepo updated
Chief Technology Officer this skillcbrock84/headcount2k—~1.6kAutomated safety check: PassMIT
Systematic Code Refactoringluongnv89/claude-howto42k—~3kAutomated safety check: PassMIT
Code Simplification for ego-litecitrolabs/ego-lite17k—~1.2kAutomated safety check: PassMIT
Code Refactoring Workflowluongnv89/claude-howto42k—~3.1kAutomated safety check: PassMIT
Cto AdvisorIbrahim-3d/orchestrator-supaconductor3814 repos~2.4kAutomated safety check: PassMIT
Ponytail Debt LedgerDietrichGebert/ponytail160k—~453Automated safety check: PassMIT

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Categories

Questions about Chief Technology Officer

What does Chief Technology Officer do?

Owns architecture, engineering delivery, infrastructure, data platform, and internal systems. Chief Technology Officer is an agent skill from cbrock84/headcount. Owns architecture, engineering delivery, infrastructure, data platform, and internal systems.

When should I use Chief Technology Officer?

Chief Technology Officer fits situations like: judge whether a technical plan is sound before it is committed to; tasks that involve Technical debt.

How do I install Chief Technology Officer in Claude Code?

Run `npx skills add cbrock84/headcount --skill chief-technology-officer -a claude-code`. Or copy the skill folder (plugins/technology/skills/chief-technology-officer in cbrock84/headcount) into .claude/skills/chief-technology-officer in your project. Claude Code loads it when a task matches its description.

How do I install Chief Technology Officer in Codex?

Run `npx skills add cbrock84/headcount --skill chief-technology-officer -a codex`. Or copy the skill folder (plugins/technology/skills/chief-technology-officer in cbrock84/headcount) into .agents/skills/chief-technology-officer in your project. Codex loads it when a task matches its description.

Can I use Chief Technology Officer in Cursor, Gemini CLI or GitHub Copilot?

Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add cbrock84/headcount --skill chief-technology-officer -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/chief-technology-officer, .gemini/skills/chief-technology-officer, .github/skills/chief-technology-officer and .opencode/skills/chief-technology-officer in your project.

What does Chief Technology Officer need to run?

SKILL.md names no scripts, command-line tools or credentials: Chief Technology Officer is instructions for the agent only.

Does Chief Technology Officer access the network?

SKILL.md contains no URLs. Any network use would come from the scripts or tools the agent runs. This is read from the text; nothing was executed.

Is Chief Technology Officer safe to install?

Our automated static check of SKILL.md found no risky patterns, such as piping downloads into a shell, reading credential files or hidden Unicode. It is not a guarantee. Review the folder before installing.

What licence does Chief Technology Officer use?

Chief Technology Officer is published under the MIT licence (the repository's licence). It allows redistribution, so the full SKILL.md is shown on this page.

How many tokens does Chief Technology Officer use?

About 1.6k tokens (SKILL.md is roughly 6.3k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full. Its references folder adds about 228 tokens, read only when the agent opens those files.

What are the alternatives to Chief Technology Officer?

Skills that share tags, products or a category with Chief Technology Officer: Systematic Code Refactoring (luongnv89/claude-howto, 42k stars), Code Simplification for ego-lite (citrolabs/ego-lite, 17k stars), Code Refactoring Workflow (luongnv89/claude-howto, 42k stars) and Cto Advisor (Ibrahim-3d/orchestrator-supaconductor, 381 stars). The comparison table on this page puts their stars, adoption, token cost, safety result and licence side by side.

Who maintains Chief Technology Officer?

cbrock84 (a GitHub user) maintains it in cbrock84/headcount, which has 2,022 GitHub stars. The repository holds 178 skills in this directory. The repository was last updated on September 17, 2026.

Source: cbrock84/headcount on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.