SkillsAdd

shipshitdev/skills

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 engineeri…

First seen Jan 20, 2026

Installation

$ npx skills add shipshitdev/skills --skill cto-advisor
View on skills.sh ↗ GitHub repository ↗

Summary

  • 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`.

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More details

Agent compatibility

Declared targets from SKILL.md / docs. Unmarked agents are not listed — the skill may still install via the CLI.

Claude Code Not declared
Cursor Not declared
Codex Not declared
GitHub Copilot Not declared
Windsurf Not declared
Gemini CLI Not declared
Cline Not declared
OpenCode Not declared

Repository health

Stars 35
License MIT
Default branch master
Open issues 1
Status Active

Skill metadata

Parsed from SKILL.md frontmatter.

Version1.0.1
LicenseMIT
More metadata
version
1.0.1
tags
leadership, engineering, architecture, strategy, metrics

Package contents

Files included with this skill beyond the listing page.

  • skill md SKILL.md 3,186 B
  • docs SUMMARY.md 610 B

History

  1. First seen on skills.sh
  2. First recorded snapshot · 168 installs

SKILL.md

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/architecturedecisionrecords.md

Technology Evaluation

See references/technologyevaluationframework.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