shipshitdev/cto-advisor
bundles/planning/skills/cto-advisor/SKILL.md
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`.
$ install --global
skillsauthnpx skillsauth add shipshitdev/library cto-advisorInstall this skill globally with one command. Works with Claude Code, Cursor, and Windsurf.
Security Scan Results
3 of 9 scanners reported clean
Some scanners were skipped, did not run, or reported a non-clean status. Review each row below.
3
Scanners Passed
9
Scanners in report
Clean
TrivyContainer and dependency vulnerability scanner
95%
Clean
SemgrepStatic code analysis for vulnerabilities
95%
Clean
mcp-scan (Snyk)Model Context Protocol security validation
95%
Skipped
Snyk (dep)Open source security scanning
50%
Skipped
Socket.devSupply chain security analysis
50%
Skipped
VirusTotalMulti-engine malware detection
50%
Skipped
CrowdStrikeAdvanced threat intelligence
50%
Skipped
OSV-ScannerOpen Source Vulnerability database check
50%
Skipped
OWASP Dep-Check
50%
Last scanned: Aug 20, 2026, 3:15 AM17.7s8 files scanned
SKILL.md
- name:
- cto-advisor
- description:
- 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
- version:
- 1.0.1
- tags:
- leadership, engineering, architecture, strategy, metrics
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-debtowns 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 |
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
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