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
- Intro call (30 min): motivation, scope they have owned, how they explain trade-offs.
- Paid take-home or pairing (2 to 3 h): a small, real slice of your product. Respect their time.
- System design (60 min): design something you actually need; listen for the questions they ask.
- Founder fit (45 min): how they disagree, how they handle ambiguity.
- 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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