How do I install the Cto Advisor skill?

Run npx skillmds add shipshitdev/cto-advisor in your terminal (requires Node.js), paste this page's agent-chat prompt into Claude, Cursor, or any MCP-connected agent, or download the SKILL.md file and copy it into your agent's skills directory.

Is Cto Advisor safe to use?

This skill has not completed SkillMD's automated safety review yet. Capability flags: executes scripts. SkillMD never runs a skill's scripts for you; review the SKILL.md before installing.

Which AI agents work with Cto Advisor?

This skill is tagged as working with Claude Code, Claude.ai, OpenAI Codex. SKILL.md is an open format, so most agents that read a skills directory can load it too.

Is Cto Advisor free to use?

Yes. Installing skills from SkillMD is free. This skill is licensed under MIT.

Who published Cto Advisor?

shipshitdev (@shipshitdev) published this skill. Their other Agent Skills are listed on their SkillMD profile.

Cto Advisor by shipshitdev — Agent Skill

Name: Cto Advisor
Rating: 4.2 (5 reviews)
Author: shipshitdev

Cto Advisor

Advises engineering leadership on direction — architecture decisions recorded as ADRs, technology and vendor evaluation, team scaling ratios, and DORA/engineering-metric targets. Reasons from org-level indicators and frameworks, never from a repository scan. Use when the user asks which technology to adopt, how to structure or scale the engineering team, whether to write an ADR, what DORA targets to hold, or mentions CTO, technical leadership, technology strategy, vendor selection, or engineering metrics. To inventory and rank the debt already sitting in a codebase, use `tech-debt`.

shipshitdev df21689 8 files · 76.7 KB Updated Sep 9, 2026

File contents

CTO Advisor

When This Activates

User mentions CTO, technical leadership, or engineering leadership
User asks how much of the engineering budget to spend paying debt down — the portfolio-level call, not the codebase inventory (tech-debt owns that)
User needs team scaling or hiring plans
User wants architecture decisions or ADRs
User asks about engineering metrics or DORA metrics
User needs technology evaluation or vendor selection

Quick Start

Tech Debt Assessment

python scripts/tech_debt_analyzer.py

Team Scaling Planning

python scripts/team_scaling_calculator.py

Architecture Decisions

See references/architecture_decision_records.md

Technology Evaluation

See references/technology_evaluation_framework.md

Engineering Metrics

See references/engineering_metrics.md

Core Responsibilities

Area	Focus
Technology Strategy	Vision, roadmaps, innovation, tech debt
Team Leadership	Scaling, performance, culture
Architecture Governance	Decisions, standards, reviews
Vendor Management	Evaluation, relationships, SLAs
Engineering Excellence	Metrics, quality, reliability

Key Ratios

Metric	Target
Manager:Engineer	1:8
Senior:Mid:Junior	3:4:2
Product:Engineering	1:10
QA:Engineering	1.5:10

DORA Metrics Targets

Metric	Elite	High
Deployment Frequency	On-demand	1/day - 1/week
Lead Time	<1 hour	1 day - 1 week
MTTR	<1 hour	<1 day
Change Failure Rate	<15%	<30%

Success Indicators

Area	Target
System uptime	>99.9%
Tech debt capacity	<10%
Team satisfaction	>8/10
Attrition rate	<10%
Features on-time	>80%

Red Flags

Increasing technical debt
Rising attrition rate
Slowing velocity
Growing incidents
Team morale declining
Budget overruns

Integration

Skill	When to Use
`performance-expert`	Optimize system performance
`security-expert`	Security architecture
`testing-expert`	Testing strategy

tech-debt — scan a real codebase and rank its debt into a register; this skill sets the investment level, that one finds the items.

For detailed operational guidance, cadences, crisis management, and templates: references/full-guide.md

---name: cto-advisordescription: Advises engineering leadership on direction — architecture decisions recorded as ADRs, technology and vendor evaluation, team scaling ratios, and DORA/engineering-metric targets. Reasons from org-level indicators and frameworks, never from a repository scan. Use when the user asks which technology to adopt, how to structure or scale the engineering team, whether to write an ADR, what DORA targets to hold, or mentions CTO, technical leadership, technology strategy, vendor selection, or engineering metrics. To inventory and rank the debt already sitting in a codebase, use `tech-debt`.license: MIT--- # CTO Advisor ## When This Activates - User mentions CTO, technical leadership, or engineering leadership - User asks how much of the engineering budget to spend paying debt down — the portfolio-level call, not the codebase inventory (`tech-debt` owns that) - User needs team scaling or hiring plans - User wants architecture decisions or ADRs - User asks about engineering metrics or DORA metrics - User needs technology evaluation or vendor selection ## Quick Start ### Tech Debt Assessment ```bash python scripts/tech_debt_analyzer.py ``` ### Team Scaling Planning ```bash python scripts/team_scaling_calculator.py ``` ### Architecture Decisions See `references/architecture_decision_records.md` ### Technology Evaluation See `references/technology_evaluation_framework.md` ### Engineering Metrics See `references/engineering_metrics.md` ## Core Responsibilities | Area | Focus | |------|-------| | Technology Strategy | Vision, roadmaps, innovation, tech debt | | Team Leadership | Scaling, performance, culture | | Architecture Governance | Decisions, standards, reviews | | Vendor Management | Evaluation, relationships, SLAs | | Engineering Excellence | Metrics, quality, reliability | ## Key Ratios | Metric | Target | |--------|--------| | Manager:Engineer | 1:8 | | Senior:Mid:Junior | 3:4:2 | | Product:Engineering | 1:10 | | QA:Engineering | 1.5:10 | ## DORA Metrics Targets | Metric | Elite | High | |--------|-------|------| | Deployment Frequency | On-demand | 1/day - 1/week | | Lead Time | <1 hour | 1 day - 1 week | | MTTR | <1 hour | <1 day | | Change Failure Rate | <15% | <30% | ## Success Indicators | Area | Target | |------|--------| | System uptime | >99.9% | | Tech debt capacity | <10% | | Team satisfaction | >8/10 | | Attrition rate | <10% | | Features on-time | >80% | ## Red Flags - Increasing technical debt - Rising attrition rate - Slowing velocity - Growing incidents - Team morale declining - Budget overruns ## Integration | Skill | When to Use | |-------|-------------| | `performance-expert` | Optimize system performance | | `security-expert` | Security architecture | | `testing-expert` | Testing strategy | ## Related - `tech-debt` — scan a real codebase and rank its debt into a register; this skill sets the investment level, that one finds the items. --- **For detailed operational guidance, cadences, crisis management, and templates:** `references/full-guide.md`

Frequently asked questions