Three Months at Handshake!
Well, I made it three months at Handshake!
Let me be clear: this is a story about fit, not failure. Sometimes you learn the most from the jobs that teach you what you don’t want, and honestly? That’s valuable, I promise!
The Good Stuff First (Because There Was Plenty)
Let’s start with what worked. The early career engineers on my team were fantastic. There’s something special about working with people who are genuinely excited about building things, and getting to mentor and provide feedback reminded me why I love this industry. We’re definitely staying in touch.
I made friends immediately! We started an accessibility club working through practical accessibility together, I joined ERGs, and spent my days on coffee walks with genuinely lovely people.
And the Handshake internship program was stellar – those interns had real projects with actual impact and were genuinely integrated into teams. I sat across from one of the interns and he was one of the funiest people I’ve ever got to just overhear talking on a day to day. One thing in particular I noticed from their end of summer projects was that every single intern in this class has a much better grasp on animation than I do. backend engineers were making animated text effects that I was so jealous of!
The Not-So-Good Stuff (Or: How I Learned I’m Not a “Move Fast” Person)
Here’s the thing about growth teams: they’re built for speed. I’m built for thoughtfulness. When I picked up a project to rewrite a Stripe implementation, I wrote a 20-page document to go along with it. I’m a thinker, a planner, someone who believes in understanding the why before hammering out the how. This was not the vibe.
Growth teams are also, fundamentally, “make money” teams. And look, I get it – companies exist to make money. But seeing exactly how the sausage gets made can be… illuminating. My values and the day-to-day realities of growth metrics weren’t exactly aligned.
And the tech stack? A 12-year-old Ruby monolith that required restarting services multiple times a day. Webpack somehow making my brand new 32GB M4 laptop run out of memory. It felt like going back in time to my early dev days, and not in a fun, nostalgic way. (I don’t want to throw the developer experience engineers under the bus here, they were dealing with a LOT, but it was rough.) It really feels petty to complain about this, but it was a challenge!
The Lessons (Because We’re All About Growth Here, Just Not That Kind)
So what did I learn from this whirlwind at Handshake?
1. Interview questions are great, but you need to listen to what’s not being said. I pride myself on asking good questions during interviews. Turns out, I need to level up my ability to spot when answers are more aspirational than actual. When no one mentions any technical challenges with a 12-year-old codebase, that’s information.
2. Team placement matters more than company fit. You can love a company’s mission and still be miserable if you’re on the wrong team. The growth team and I were fundamentally mismatched from day one.
3. Know your work style and defend it. I’m not a “ship it and fix it later” person. I’m a “let’s think about this, document it, and build something we won’t hate in six months” person. Neither is wrong, but trying to be something you’re not is exhausting.
4. Brain drain is real and it’s obvious. Handshake AI is a really exciting opportunity, and the company has responded by putting a ton of resources behind it. When the AI team is pulling talented engineers from every other team, and your team’s product roadmap is basically nonexistent, that’s a signal.
The Takeaway
Here’s what it comes down to: Handshake wasn’t going to get the best work out of me, and I wasn’t going to thrive there. That’s not a failure on either side – it’s just a mismatch.
I spent my last days there doing what I do best: going on coffee walks and making sure everyone knew the specific things I appreciated about working with them. Because even when something doesn’t work out, the people you meet and the lessons you learn still matter.
Am I disappointed it didn’t work out? A little. Am I grateful for the clarity it gave me about what I actually want from my next role? Absolutely. I want a role that allows for creativity, gives space for brainstorming and collaboration, and doesn’t make my laptop cry.
Sometimes the best career moves are the ones that teach you where not to go next.
Stay tuned for news about what’s next (spoiler: it involves a lot more thinking, a lot more creating and prototyping, and exactly zero webpack memory errors).
P.S. – To my former teammates at Handshake: you’re doing great work, and I’m rooting for you. To anyone considering joining: ask about the team placement, really probe those technical architecture answers, and make sure your work style aligns with the team’s velocity. Reach out if you’re interested in talking about any role in particular, I would honestly recommend working at Handshake for a particular type of software engineer!