Headed for the Exit: the Great Engineering Leader Career Break

• 1. The job got (much) worse

• • 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

• “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’.”

• “Shipping software became all about speed. Finding differentiation with your product in the market is brutal, and speed / go-to-market becomes the biggest differentiator. Craft, quality, and care going into the product are taking a backseat.”

• • At Director+ level, a big part of the job is making strategic decisions that grow the business and help the company get ahead. It’s a nice-to-have for an engineer to possess business acumen, but director-and-above folks use it much more than most individual contributors (ICs). Great engineering leaders are good at understanding business performance and outlook.
• A company that adopts AI rapidly usually falls into one of three buckets:
• • “AI-native”, building & selling AI products. The large AI labs and a select few “AI-native” startups are thriving, but many AI startups with VC funding struggle. Engineering leaders know this, and that their equity – usually issued as options – could end up worthless.
• • Software startups threatened by AI-native businesses
• • Unaffected by AI.

• Leaving due to equity becoming worthless

• It’s new to see people signing out of large companies for feeling like they’re lagging behind in adopting new AI workflows.

• Like many others, I see the future of software development is with AI. If you don’t get hands-on with your team, working with AI tools day-in, day-out, you’re falling behind.

My plan is to get on the cutting edge of things through a mix of academia and consulting AI companies. I am not saying the plan is perfect, but I need more time to do things differently than I had in my job.”

• Consider this: if you stay in your job for two more years, do you expect to find career opportunities at cutting-edge companies in the future? If the answer is “no”, then there’s a risk in just staying put. Joining an uncertain startup or taking a career break to develop AI expertise is also risky, but the outcomes may be more controllable than letting your skillset become outdated, relatively quickly.

• The VPE role used to be primarily about deploying the dark arts to defend engineers from the roadmap, and now everyone thinks that’s BS and leaders are under tremendous pressure to inflect velocity or GTFO (get the f*** out).

Engineers are unhappy (don’t make me tokenmaxx, bro!), product and design sending slop PRs, and everyone good has left for a lab.

• “Fullstack engineer” is mainstream, and was even before AI. Fullstack engineering was becoming relevant a few years ago in terms of a single engineer working on both the front and backends, instead of having a frontend engineer building the UI, and a backend engineer working on backend services. Fullstack frameworks like Next.js or Ruby on Rails made all this pretty easy before AI. Today with AI coding agents, you can rely on them to write decent code on platforms you’re unfamiliar with. There’s now little to no reason why a project would need multiple devs with different specializations.

• On an individual project, you often cannot have more than two people working on it.

This is because each engineer is already running several agents. And so as an engineer, you’re already fighting against your agents, which are stepping on each other’s toes on implementation. And in this setup, you just cannot have that many humans, who also come with all their agents!

• Demand for frontend engineers and native iOS+Android engineers keeps dropping with the trend of smaller engineering teams. Source: The tech jobs market in 2026
• Tech companies have been flattening their org structures for three years now. We first covered the trend for fewer middle managers back in 2023, when Meta drastically reduced manager positions. The trend has not stopped, and many – if not most – companies have increased the number of reports each engineering manager has, while reducing the number of layers in their organization.