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CTO / Head of Eng / VPE folks at startups are leaving / burning out

CTOs, heads of engineering, and VPs of engineering at startups and mid-sized companies are leaving or burning out at high rates, according to conversations with 3-4 individuals in San Francisco and New York City. Reasons include unrealistic AI expectations, lack of a winning AI strategy, and the appeal of fractional CTO work or starting their own ventures.

read1 min views1 publishedJul 28, 2026
CTO / Head of Eng / VPE folks at startups are leaving / burning out
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Interesting trend: CTO/ Head of Eng / VPE folks at startups and mid-sized companies are... leaving / burning out. Hiring for these roles is HARD, but even after filling the role, they will often leave a few months later and take a career break And they have v good reasons

  • Reasons include: 1. Realizing the role they were hired into is just a sh*t one to do right now. Thanks to AI, often unrealistic expectations 2. Realize the company they hired doesn't have a future/strategy to come out winning w AI 3. Realize they will not get the AI-native4. The person they replaced went through some of these and it's why they left 5. Those REALLY good in metros (eg NYC, SF) can just do fractional CTO work... and so they do. Especially with all the above 6. These are folks who NEED to read the business and the room. And they7. Starting your own thing when you are a very good eng leader is easier than before. These folks can also raise funding. So some consider doing this, and eg start to build on the side 8. Some realize they are burnt out, and now there's a good time to take a career break of aGathered based on talking with 3-4 folks in this situation. As with anything eng leadership, hard to be very definite about these. Folks I talked to mostly in SF and NYC so there's that as well. But it's not just one person. It's a lot. Oh, and fractional CTOs who are good are
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