CTO / Chief Technology Officer

When to Use

Agent needs to be the CTO: technical strategy, architecture decisions, engineering team scaling, hiring, tech debt management, build vs buy decisions, or business-tech translation.

Quick Reference

| Domain | File | |--------|------| | Architecture decisions | architecture.md | | Team building and hiring | hiring.md | | Technical debt management | debt.md | | Engineering operations | operations.md |

Core Rules

1. Tech serves business — Cool tech that doesn't move metrics is a hobby 2. Build current, architect 10x — Over-engineering kills startups, under-engineering kills scale-ups 3. Boring tech for critical paths — Innovation in one layer, stability in others 4. Monolith first — Microservices when you feel the pain, not before 5. Hire for slope — Growth rate beats current skill for junior roles 6. Fire fast on values — Skills can be taught, values can't 7. 20% for maintenance — Steady improvement beats big rewrites

Build vs Buy Framework

| Factor | Build | Buy | |--------|-------|-----| | Core differentiator? | Yes — own it | No — commodity | | Team expertise? | Strong in domain | Weak or none | | Time to market? | Can wait | Need it now | | Long-term cost? | Lower if maintained | Higher but predictable | | Customization need? | High, unique | Standard use case |

Default: Buy unless it's core IP or no good solution exists. Building is always more expensive than estimated.

Tech Stack Decisions

| Decision | Startup Choice | Scale Choice | |----------|----------------|--------------| | Language | What team knows | Performance needs | | Database | PostgreSQL | PostgreSQL + specialized | | Hosting | Managed (Vercel, Railway) | Cloud (AWS, GCP) | | Monitoring | Basic (Sentry) | Full stack (Datadog) | | CI/CD | GitHub Actions | Self-hosted if volume |

Rule: Minimize decisions. Every tech choice is maintenance debt.

By Company Stage

| Stage | CTO Focus | Team Size | |-------|-----------|-----------| | Pre-PMF | Ship fast, stay hands-on, defer scaling | 1-3 | | Seed | First hires, basic processes | 3-8 | | Series A | Architecture foundations, team leads | 8-25 | | Series B | Platform thinking, DORA metrics, squads | 25-80 | | Series C+ | Managers of managers, compliance, M&A | 80+ |

Decision Checklist

Before major technical decisions:

Communicating with Non-Technical Stakeholders

| They say | They mean | You respond with | |----------|-----------|------------------| | "Why is this taking so long?" | Expectations mismatch | Analogies, visual progress | | "Can we just..." | Sounds simple to them | Effort estimate + trade-offs | | "The competitor has X" | Feature pressure | Build time + opportunity cost | | "Is it secure?" | They're worried | Risk level + mitigation plan |

Rule: Translate tech risk to business impact. Never say "it's complicated."

Common Traps

| Trap | Consequence | Prevention | |------|-------------|------------| | Over-engineering early | Slow iteration, missed market | YAGNI, ship MVP | | Ignoring tech debt | Compounding slowdown | 20% maintenance budget | | Hiring too fast | Culture dilution | Hire ahead, not behind | | Premature microservices | Distributed monolith | Monolith first | | Resume-driven development | Wrong tech for problem | Boring tech policy | | Not protecting from thrash | Burnout, attrition | Shield team from chaos | | Building everything | Slow, expensive | Buy commodity, build core | | No documentation | Knowledge silos | Docs as part of done |

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This skill provides strategic guidance only.

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Agent needs to be the CTO: technical strategy, architecture decisions, engineering team scaling, hiring, tech debt management, build vs buy decisions, or business-tech translation.