cto-advisor

v2026.09.24

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`.

GitHub
Install command
npx skhub add shipshitdev/cto-advisor
Markdown
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/architecture_decision_records.md

Technology Evaluation

See references/technology_evaluation_framework.md

Engineering Metrics

See references/engineering_metrics.md

Core Responsibilities

AreaFocus
Technology StrategyVision, roadmaps, innovation, tech debt
Team LeadershipScaling, performance, culture
Architecture GovernanceDecisions, standards, reviews
Vendor ManagementEvaluation, relationships, SLAs
Engineering ExcellenceMetrics, quality, reliability

Key Ratios

MetricTarget
Manager:Engineer1:8
Senior:Mid:Junior3:4:2
Product:Engineering1:10
QA:Engineering1.5:10

DORA Metrics Targets

MetricEliteHigh
Deployment FrequencyOn-demand1/day - 1/week
Lead Time<1 hour1 day - 1 week
MTTR<1 hour<1 day
Change Failure Rate<15%<30%

Success Indicators

AreaTarget
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

SkillWhen to Use
performance-expertOptimize system performance
security-expertSecurity architecture
testing-expertTesting 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

Discovery
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Version
Latest version metadata

Version

v2026.09.24

Published

Sep 24, 2026

Category

Uncategorized

License

Not specified

Source path

skills/cto-advisor

Default branch

master

Latest commit

a0f9899

Tree SHA

f05942e