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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Sort replies: Relevant Recent Liked
Replying to @GergelyOrosz
I’m seeing the same thing with really good Heads of Talents. Burning out, taking breaks. When other teams burn out, recruiting gets called in to save the day. Find another unicorn who can somehow make it work.
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Replying to @GergelyOrosz
It’s such an easy role- these people are weak, their bloodline is weak, and history will forget them.
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Replying to @GergelyOrosz
I burnt out after CTOing a startup for 6 months back in 2018, but that was because I realized I hated spending 24/7 on hiring. Architecting the app was fun, hiring was not. That's why I've climbed back down the corporate ladder.
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Replying to @GergelyOrosz
CTOs have to do most of the (technical) work and take the onus for such decisions which often make or break the company; but get a fraction of the CEO upside! It is a fundamentally mispriced role IMO. (In terms of "market" comp rates vs realities, espec for true tech companies.)
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Replying to @GergelyOrosz
Why I went back to IC. Being an IC coder is fun.
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Replying to @GergelyOrosz
Not only at startups. I've seen the same phenomenon at large corporations as well.
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Replying to @GergelyOrosz
Trying to push AI into an unwilling org is like pushing a rope into a pinhole.
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Replying to @GergelyOrosz
The AI pilled CEO sending PRs on GitHub does not help.
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Replying to @GergelyOrosz
It’s wild to me that software devs and engineers are in this hell. While we’re over here in InfoSec seeing a very bright future.
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Replying to @GergelyOrosz
Thats a shame, meanwhile CPOs seem to be running the tables (again small sample size)!
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Great discussion by @GergelyOrosz and @levelsio on related topics. Some thoughts: 1. Multiple compression on everything not AI. 2. Less niche markets. More of a winner takes most dynamic due to AI. I mean, think about all the EU versions of Ebay, Zillow, Doordash etc. Much easier to localize or fix more niche product gaps with AI.
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Replying to @GergelyOrosz
these roles turned into pure fire fighting. VP of eng used to mean team strategy, now it’s constantly managing technical debt and fixing broken agent deploys at 2am.
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Replying to @GergelyOrosz
I believe it. Times are changing so aggressively, being right in the middle with full accountability but limited power a horrible combo
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Replying to @GergelyOrosz
what’s so hard about installing claude code on all the engineer laptops?
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Replying to @GergelyOrosz
I actually like working with people and helping them succeed. Sometimes constraints are shit and you need to see what you can do about it.
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Replying to @GergelyOrosz
Yes sir - can vouch for that
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Replying to @GergelyOrosz
Consequence of the market being unreasonable? I wouldn’t be surprised if so.
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Replying to @GergelyOrosz
Companies do not care enough about making work something you want to come to everyday.
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Replying to @GergelyOrosz
Taking six months off after that grind is so real
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Replying to @GergelyOrosz
I can see similar happening to design and product execs tbh: many left, went back to building or founded a company
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Replying to @GergelyOrosz
That's rough. It's definitely a tough market for those roles right now. Hope things get better for them.
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Replying to @GergelyOrosz
Things are moving faster and faster, most people can’t keep up regardless of how hard working or committed you are. Many are probably questioning what they are really after. Unless lives are at stake, what exactly is the urgency in all this.
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Replying to @GergelyOrosz
Every founder out there who somehow secured some investment think they are the next Steve, Elon and demand waaay to much for what they pay. Stats are there, you could only motivate people so much with your shitty stock options which are likely going to worth nothing in 5 years, so not surprised at all.
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Replying to @GergelyOrosz
Points 5 and 7 resonate with me perfectly. I’ve never been burnt out or frustrated as a CTO mostly because I never say yes to an opportunity I don’t immediately the value I add and over what timeframe within an agreed autonomous budget allocation. My fear is too many CTO’s accept roles without any leverage the moment they walk in the door. Most CTO’s are just not commercial enough and prefer to be left in the codebase firefighting EXCO changing priorities. Obviously I am generalising but it’s my experience and I wish it was different for our excellent colleagues. Far smarter than me in most cases. But allow themselves to be a push over at times. 😢
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Replying to @GergelyOrosz
I’m noticing the same trend in my network, too. The opportunity cost is just immensely high to spend your time on things you are not truly 100% into. That’s why a lot of folks decide to go and start their own company, instead.
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Replying to @GergelyOrosz
wow, you just described my last year! I was head of eng at a small b2c for 8 months left because the expectations to comp were unreasonable. now i’m back as an EM at a solid company and very happy
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Replying to @GergelyOrosz
To be honest, I don't think I'd want to be a CTO at the moment. Things are moving so fast it's literally impossible to plan for any real long term strategy, whilst all the while the expectations on CTOs are more than ever. It's not the same but even in my role as a tech lead it's really exhausting and mentally draining at the moment. It's why I often really just yearn for how things were a lot of the time, the advances are great but they kinda destroy people in all sorts of ways.
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Replying to @GergelyOrosz
How could being a CTO be that hard? Men used to go to war.
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Replying to @GergelyOrosz
Are they getting any equity? Seems like a shit deal if you get 1yr cliff, work like a dog and burn out in 6-9mo. Company gets all the adv of the performance and gives up 0-equity. The 1yr cliff needs to go esp in startups. Vests should be monthly with max 3mo cliff
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Replying to @GergelyOrosz
Another pattern I've noticed: the founder archetype is often a sales archetype: exceptional at selling a vision but not always grounded in the realities of building AI. The CTO is then left trying to deliver a grand vision that was already sold to customers, while the product demands patience and iteration. Nowadays it’s viable for a strong CTO to validate an idea, build the solution patiently, and then sell it rather than relying on a salesman archetype that's out of sync with engineering reality. Basically when business and engineering aren't aligned, everyone loses.
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Replying to @GergelyOrosz
He has talked with 3-4 friends and made his analysis based on that. That's the source.
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