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
Jul 27, 2026 · 8:52 PM UTC
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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-native experience they know they need to get to thrive long-term, and the setup won't allow them to get it, so it would be career suicide
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4. 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 they realize joining the right company v important now. Also very hard
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7. 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 a few months
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Gathered 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 getting massive pulls to go fulltime... most refuse!
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So many great additions. From @umachingunde this is absolutely spot on as well at many places:
The most important trend imo is that this is also downstream of ‘founder mode’. Talking to some peers who experienced either their ceos getting ai-pilled and/or going founder mode the job increasingly was miserable low ROI.
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