shipshitdev/cto-advisor
bundles/planning/skills/cto-advisor/SKILL.md
Technical leadership guidance for engineering teams, architecture decisions, and technology strategy. Includes tech debt analyzer, team scaling calculator, engineering metrics frameworks, technology evaluation tools, and ADR templates. Use when assessing technical debt, scaling engineering teams, evaluating technologies, making architecture decisions, establishing engineering metrics, or when user mentions CTO, tech debt, technical debt, team scaling, architecture decisions, technology evaluation, engineering metrics, DORA metrics, or technology strategy.
$ install --global
skillsauthnpx skillsauth add shipshitdev/library cto-advisorInstall this skill globally with one command. Works with Claude Code, Cursor, and Windsurf.
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TrivyContainer and dependency vulnerability scanner
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Socket.devSupply chain security analysis
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Last scanned: Jun 4, 2026, 6:43 AM316.4s8 files scanned
SKILL.md
- name:
- cto-advisor
- description:
- Technical leadership guidance for engineering teams, architecture decisions, and technology strategy. Includes tech debt analyzer, team scaling calculator, engineering metrics frameworks, technology evaluation tools, and ADR templates. Use when assessing technical debt, scaling engineering teams, evaluating technologies, making architecture decisions, establishing engineering metrics, or when user mentions CTO, tech debt, technical debt, team scaling, architecture decisions, technology evaluation, engineering metrics, DORA metrics, or technology strategy.
- license:
- MIT
- version:
- 1.0.0
- tags:
- leadership, engineering, architecture, strategy, metrics
CTO Advisor
Strategic frameworks and tools for technology leadership, team scaling, and engineering excellence.
When This Activates
- User mentions CTO, technical leadership, or engineering leadership
- User asks about tech debt or technical debt
- 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 |
For detailed operational guidance, cadences, crisis management, and templates: references/full-guide.md
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