The First-Time CTO
Background: Technical co-founder who learned on the job
Built the MVP. Knows every line of code. But hit their ceiling. Can't scale systems or teams. Defensive about technical debt they created. Struggles to hire and evaluate senior talent.
The Pattern
The First-Time CTO is usually a technical co-founder who built the first version of the product. They're smart, scrappy, and deeply committed. The early code exists because of their nights and weekends.
But what got you here won't get you there. The skills that build an MVP (speed, pragmatism, doing everything yourself) become liabilities at scale. Now you need architecture, processes, and the ability to lead through others.
First-Time CTOs often don't realize they've hit their ceiling. They're defensive about the codebase they built ("it works!") and threatened by senior hires who might expose their gaps. The result is a team that can't grow and a product that can't scale.
Warning Signs
- "Only they understand the code." The codebase is tribal knowledge. No documentation, no patterns, just "ask [CTO]."
- Can't retain senior engineers. Good people join, get frustrated, and leave. The CTO blames "culture fit."
- Everything is a firefight. No proactive work, just reacting to what's broken. Technical debt compounds.
- Defensive about the architecture. Any suggestion for improvement is met with "you don't understand the constraints we had."
- Struggles to delegate. Reviews every PR. In every meeting. Can't let go.
- Hiring below their level. Unconsciously avoids people who might be better than them.
Why This Is Hard
This is one of the most emotionally difficult situations in startups. The First-Time CTO is often a co-founder. They've sacrificed for the company. They're not a bad person, they're just in over their head.
The CEO often knows something is wrong but feels guilty addressing it. "They've been here since day one." "They're my friend." "Maybe they just need more support."
Meanwhile, the engineering team stagnates, good people leave, and the product falls behind. Loyalty becomes a liability.
How to Fix It
- Get an honest external assessment. You need someone who can evaluate the CTO without politics. Is this a coaching problem or a ceiling problem?
- Separate the role from the person. Maybe they're a great engineer but not a CTO. Can they move to a principal/architect role?
- Invest in coaching. Some first-time CTOs can grow with the right support. But they have to want it.
- Bring in senior help. A VP of Engineering or strong tech leads can complement the CTO's gaps, if they'll accept it.
- Have the conversation. Often the CTO knows they're struggling. A direct, caring conversation can unlock options.
How I Can Help
I've been a first-time technical leader. I've also coached several through this transition. The key is honest assessment: can this person grow into the role, or do they need a different one?
I can help you evaluate the situation objectively, have the difficult conversations constructively, and find a path forward that respects both the person and the company's needs.
Recognize this pattern?
30-minute diagnostic call.
Tell me what's happening. I'll tell you the one thing to fix first.