A CTO behind the curtain

More Herding Cats Than Writing Code

I used to be an Engineer, now I wonder why I ever took up this job. I was deeply immersed in being an engineer; you know, headphones on, solving complex problems, in a state of flow for hours. But these days, as the CTO of a mid-stage Silicon Valley startup, my calendar resembles a Tetris game of meetings, and the last time I spent a whole afternoon writing code was, well, let’s say I had more hair back then (I guess you get the point), it was years ago.

Let me paint you a picture. We’re a team of about 80, now 25 engineers, 5 product managers, a couple of designers, and the usual growing pains. We’ve raised a solid Series B. Revenue’s coming in. The board’s impatient. And suddenly, everyone is looking to me to “scale the team,” “harden the platform,” and “accelerate velocity.”

Here’s what that actually looks like:

  • Hiring is a full-time job in itself. Finding sound engineers is tough. Finding good startup engineers people who can thrive in chaos, move fast without breaking everything, and tolerate the occasional 2 a.m. PagerDuty alert is nearly impossible. We interview like crazy, make offers. And then watch as Big Tech swoops in with comp packages we can’t match.
  • Tech debt? We have a mountain of it. When you’re sprinting to ship version 1, then version 2, and close your next funding round, clean code isn’t the priority. Now, every engineering all-hands starts with the same slide: “Debt cleanup: Q3 focus.” I’m not sure we’ve had a quarter without that slide.
  • The psychological load is real. Half my week is spent coaching burned-out engineers, de-escalating inter-team friction, and convincing product managers that no, we can’t build five new features this sprint. Startups are emotional rollercoasters. The code is the easy part.

But this is also why I’m still here, every once in a while, I see something magical happening here. A prototype comes together and wows a customer. An engineer solves a problem that stumped everyone for weeks. A big client signs a multi-year deal. Those little moments remind me why I chose this life over a comfy job at Google.

And if you ask me, do I miss the coding days of my life? Absolutely yes. But building a company, watching it grow, helping others level up, and seeing a random idea become a reality is all a different thrill. Messy, stressful, but totally worth it.

Now, if only I could find time to refactor that old API module.

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