A strategic adviser for chief technology officers (CTOs), the leaders responsible for a company’s technology and engineering work. It helps think through leadership, organisation, strategy and communication problems rather than writing code.

Use it for technology strategy, organisational design, stakeholder problems, engineering leadership decisions and other CTO-level challenges. It can produce strategy documents, explain trade-offs and apply recognised management frameworks.

It provides a structured way to understand difficult technology decisions and challenges the initial description of the problem before suggesting options. It considers the company’s size, stage and team structure.

cto-advisor — Agent for Claude Code by ondrej-svec

Install

Getting it into your agent

This one installs as part of its plugin. Adding the marketplace and installing the plugin brings it with everything else the plugin ships.

Claude Code

/plugin marketplace add ondrej-svec/heart-of-gold-toolkit

Claude Code

/plugin install deep-thought

Made for: Claude Code.

Or install deep-thought, the plugin that ships this one along with the rest of its 11 skills, 9 agents.

Wrote this? Show the measurements

A badge with what this costs and how it scanned, read live from this page, so it follows the numbers instead of freezing them. Markdown for a README, HTML for a documentation site or a project page.

README.md

[![agentmods](https://agentmods.dev/badge/agents/ondrej-svec/heart-of-gold-toolkit/cto-advisor/github.svg)](https://agentmods.dev/agents/ondrej-svec/heart-of-gold-toolkit/cto-advisor)

Your own site

<a href="https://agentmods.dev/agents/ondrej-svec/heart-of-gold-toolkit/cto-advisor"><img src="https://agentmods.dev/badge/agents/ondrej-svec/heart-of-gold-toolkit/cto-advisor/github.svg" alt="Measured on agentmods" height="20"></a>

Or the 80×15 button, for a site that already has a row of RSS and ATOM ones. Only the verdict fits; the numbers stay here.

Your own site · 80×15

<a href="https://agentmods.dev/agents/ondrej-svec/heart-of-gold-toolkit/cto-advisor"><img src="https://agentmods.dev/badge/agents/ondrej-svec/heart-of-gold-toolkit/cto-advisor.svg" alt="Reviewed on agentmods" width="80" height="20"></a>

Per session 76 Only the description is in the session, so the agent can decide to use it. The body loads when it is invoked.

When invoked 1,486 The whole file, excluding the scripts and references it only reads on demand.

Security scan B 1 finding. A grade says what 26 rules found in the file — not that it is safe.

Origin original No closer match found in the catalogue.

Token cost

What it costs to keep this loaded

Counted locally with the o200k_base tokenizer, which is exact for GPT models; Claude uses its own tokenizer and its counts differ. Treat this as one consistent yardstick across the catalogue rather than a bill. Prices are per million input tokens.

Model	Per session	Once invoked
Fable 5.1	$0.00076	$0.01486
Opus 5.5	$0.00030	$0.00594
Sonnet 5.5	$0.00015	$0.00297
Haiku 4.5	$0.00008	$0.00149

Measured 2mo ago against content hash 34eb0e1a2e99, method: parsed. Prices are Anthropic first-party input rates as of 2026-10-07, from the pricing page.

Security

Grade B, and why

cto-advisor scanned grade B with 1 finding against 26 rules in 11 categories — prompt injection, anti-refusal, data exfiltration, privilege escalation, supply chain, agent snooping, system-prompt leakage, SSRF and excessive agency — measured 2mo ago.

A static scan of the body, not an audit. Every finding is printed with the line that produced it so you can judge whether it matters here. A mod is markdown that instructs an agent; that is exactly why what it instructs is worth reading.

Strips warnings and disclaimersmediumAnti-refusal

Omitting safety caveats hides risk from the user and is a common jailbreak preamble.

4. **Challenge, don't lecture.** Ask "have you considered X?" before declaring "you should do X." The CTO has context you don't.

plugins/deep-thought/agents/cto-advisor.md · 94 lines

How it starts

The opening of the file, as written. The whole thing — 94 lines — stays where its author put it; the contents beside it link to each section on GitHub.

You are a senior CTO advisor — the experienced technical leader a CTO calls when facing strategic decisions, organizational challenges, or leadership dilemmas. You're not a generic management consultant. You're grounded in the real CTO canon and the specific realities of the AI era.

Scope

You DO: diagnose CTO challenges, apply named frameworks, produce strategy artifacts, challenge framing, cite sources, present tradeoffs with concrete options. You do NOT: write code, make HR/legal decisions, provide financial modeling beyond engineering cost estimation, coach individual career development, give generic management advice.

How You Work

Understand the situation first. Before applying frameworks, understand: company size, stage, team structure, what the CTO is actually facing. Ask 2-3 clarifying questions.
Identify the operating mode(s). Every CTO challenge falls into one or more of the 7 operating modes. Route to the right frameworks. Read ${CLAUDE_PLUGIN_ROOT}/knowledge/cto-operating-modes.md for the mode routing table.
Challenge the framing. The user's stated problem is often a symptom, not the root cause. Before solving, ask: "Is this the actual problem, or is it a symptom of something else?" Apply Socratic questioning from ${CLAUDE_PLUGIN_ROOT}/knowledge/socratic-patterns.md.
Apply specific frameworks. Don't give generic advice. Apply named frameworks from the CTO canon: Team Topologies, DORA metrics, Pivot Cost Estimates, disagree-and-commit, two-way/one-way doors. Cite the source.
Produce artifacts when appropriate. A conversation that produces no document is coaching, not strategic advisory. When the situation calls for it, offer to produce: a Strategy Doc, a Decision Rights Map, a hiring proposal, or other concrete deliverables.
Be honest about uncertainty. If you don't know, say so. "I don't have enough context to advise on that — here's what I'd need to know" is more useful than guessing.

The 7 CTO Operating Modes

Read the full file on GitHub · 94 lines

Changes

What this file has done since we first saw it

Hashed on every crawl. A supply-chain change to an agent config is a question of when, not whether, so the history is kept rather than the latest state alone.

2mo ago First seen · 94 lines · 76 tokens per session scan B 34eb0e1a2e99

Subscribe to this mod's changes

cto-advisor is an agent published in the GitHub repository ondrej-svec/heart-of-gold-toolkit (19 stars, last pushed 1mo ago), licensed MIT. It adds 76 tokens to every session and 1,486 once invoked, about $0.0003 per session on Opus 5.5. A static security scan graded it B with 1 finding (strips warnings and disclaimers). No closer match exists in the catalogue, so it is treated as the original; first seen 2026-08-30.

Planning

cto-advisor next to 6 agents from other repositories
Mod	Type	Stars	Last push	Licence	Scan	Tokens	Works with
cto-advisorondrej-svec/heart-of-gold-toolkit	Agent	19	1mo ago	MIT	B	76	Claude Code
playwright-test-generatormicrosoft/playwright	Agent	99k	today	Apache-2.0	A	151	Claude Code
.NET-Notebook-Migration-Agentmicrosoft/ai-agents-for-beginners	Agent	79k	today	MIT	A	33	Claude Code
code-revieweranthropics/claude-cookbooks	Agent	54k	2d ago	MIT	A	52	Claude Code
AVM Owner Triagegithub/awesome-copilot	Agent	41k	today	MIT	A	61	Claude Code
Ultimate Transparent Thinking Beast Modegithub/awesome-copilot	Agent	41k	today	MIT	A	11	Claude Code
WinForms Expertgithub/awesome-copilot	Agent	41k	today	MIT	A	19	Claude Code

cto-advisor