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👋 Hi, this is Gergely with a subscriber-only issue of the Pragmatic Engineer Newsletter. In every issue, I cover challenges at Big Tech and startups through the lens of engineering managers and senior engineers. If you’ve been forwarded this email, you can subscribe here.
Headed for the Exit: the Great Engineering Leader Career Break
Trend: more CTOs, VPEs, and Heads of Engineering are walking away from their high-status, in-demand positions. There are many reasons, mostly related to AI, and to "founder mode"
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In my ~20 years in this industry, I’ve not seen as many capable engineering leaders opting out or taking prolonged breaks as now, with some high-ranking engineering leaders – CTOs, VPs of Engineering, heads of engineering, etc. – quitting their high-status roles and departing, if not into the sunset, then at least with nothing lined up.
To find out what might be behind this spate of sign-outs, I talked with almost 20 engineering leaders currently on a career break – or seriously considering one – and they let me into their personal reasons for deciding to jam the brakes on their careers. Thanks to everyone who shared their input!
Today, we cover:
Ten of the most common reasons for quitting, sometimes without the next gig lined up:
1. The job got (much) worse
2. The startup is “losing” and becoming worthless
3. Not being AI-native enough for other skills to be relevant
4. Their predecessor saw the “writing on the wall”
5. Long hours – rarely decisive
6. Smaller teams mean less need for leaders
7. Fractional CTO work preferred over fulltime positions
8. AI startups pay ICs more than non-AI startups pay executives
9. Quitting to launch their own business
10. Burnout
“Founder mode” looks here to stay, so how to deal with it? And has it made the CTO and VPE roles become “low ROI”?
‘Work at companies that truly want to drive change’. A personal account from someone who took the VP of Engineering role at Gitpod (later, Ona, now acquired by OpenAI) and enjoyed a rewarding experience. Matt Boyle says he interviewed the employer beforehand on whether their business truly leans into the changes brought by AI.
The bottom of this article could be cut off in some email clients. Read the full article uninterrupted, online.
“Just me?”
I was recently messaged by a head of engineering in San Francisco, who said:
“I’m talking to four startups in San Francisco about the head of engineering roles. Pretty normal.
But one interesting pattern is how founding CTOs/heads of engineering are stepping away to take a full career break. We’re talking about two of these four startups. And these are good startups!
Have you seen this trend? I have a small number of data points here, so you might have a broader view.”
I asked around privately, and it turns out a majority of the CTO-level folks I spoke to are considering the very same thing, or are actually in the process of leaving the office for a long spell away; 6/10 engineering leaders said they’re on the way out.
1. The job got (much) worse
Unrealistic expectations, including about AI, by founders and CEOs are the leading cause of jobs turning bad for CTOs and VPEs right now in 2026:
CTO expected to magically transform the company to be “AI-native”
CTO must make significant engineering cost cuts of up to 20-50%, including morale-sapping job cuts
“Do more with less” equals shipping more with fewer people (e.g., no backfills)
CTO faces pressure on business results as AI coding bills rack up
Founder slop: they want wonky AI prototypes shipped as full-blown products within weeks
Hands-on founders with “AI psychosis” make the job predictably harder, according to one CTO who just signed out of his job:
“Managing ‘AI psychosis’ with founders and executive peers has become very difficult. For example, what do you do when a founder ships a 60,000-line pull request into the product, gleaming with joy at how much more productive they’ve become with AI? They won’t see all the issues with that PR, and how do you bring up that they’ve created a massive amount of tech debt? Especially without looking like a ‘Debbie Downer’.”
Founder slop issues begin when top leaders get excited about AI’s capability, then get hands-on and start issuing PRs, and shipping code to production. It can cause issues across the board:
Accountability. Who’s oncall when founder-shipped code breaks? In the “you build it, you own it” culture of startups, it’s confusing when a founder gets hands-on while not owning their work.
Quality out the door: if a founder’s half-baked features are accepted, it sends the wider message that quality does not matter. Some people may adopt this attitude to their own work.
A founder can overrule whatever was previously agreed with the CTO or VPE about what to build next. Vibes the founder has or feels are reason enough.