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Hiring Your First Senior Engineer

A CTO’s guide for founders: when to hire, what to test, and the mistakes that cost months.

Signs you are ready

  • The founders are the bottleneck on every technical decision.
  • Releases slip because nobody owns quality or delivery.
  • You can describe the next 12 months of product work.
  • You can afford a senior salary for at least 18 months.

What the role should own

  • Delivery: shipping on a predictable rhythm.
  • Quality: tests, reviews and a release process.
  • Architecture: decisions written down with their reasons.
  • Hiring: help shape the next two or three hires.

An interview loop that works

  1. Intro call (30 min): motivation, scope they have owned, how they explain trade-offs.
  2. Paid take-home or pairing (2 to 3 h): a small, real slice of your product. Respect their time.
  3. System design (60 min): design something you actually need; listen for the questions they ask.
  4. Founder fit (45 min): how they disagree, how they handle ambiguity.
  5. References: ask what they were like in a bad week, not a good one.

Red flags

  • Cannot explain a past decision they would now reverse.
  • Wants to rewrite everything before understanding it.
  • Talks only about tools, never about users or trade-offs.
  • No interest in mentoring or documentation.

Their first 90 days

  • Days 1 to 30: ship something small, map the system, list the risks.
  • Days 31 to 60: fix the top delivery or quality bottleneck.
  • Days 61 to 90: agree a written technical roadmap with the founders.
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