Well, I made it three months at Handshake!
Let me be clear: this is a story about fit, not failure. Sometimes the most valuable career experiences are the ones that teach you what you don’t want. After 25 years of building things on the internet, I’ve learned that knowing what doesn’t work for you is just as important as knowing what does.
The Good Parts (And There Were Many)
The early career engineers on my team were incredible. There’s something special about working with folks who are genuinely excited about building things – that energy where every new feature feels like it could change everything. Getting to mentor and provide feedback reminded me why I’ve stuck around tech this long. We’re absolutely staying in touch.
I made friends immediately! We started an accessibility club working through practical accessibility together. I joined ERGs, went on endless coffee walks with genuinely lovely people and made friends.
The internship program deserves its own shoutout. These weren’t “fetch coffee and fix typos” internships – these interns had real projects with actual impact. I sat across from one intern who was genuinely one of the funniest people I’ve ever gotten to overhear day to day. Their end-of-summer presentations? Every single intern had animation skills that made me jealous. Backend engineers were making text effects that looked like they belonged on a Stripe landing page. Their use of Figma (they named layers!!) put me to shame.
Where Things Went Sideways
Growth teams are built for a specific kind of engineer, and it turns out I am not that engineer.
I pick up a project to rewrite our Stripe implementation – we’re a subscription product with complex billing, different tiers, educational discounts, the works. The existing code? Zero documentation. No one could tell me why we charged cards this particular way or what edge cases had broken the last three attempts. So I wrote a 20-page document mapping out the entire system. This was literally what I was hired to do: bring structure to the chaos.
The team was all “move fast, push up, fix later” folks. They wanted to ship something in a sprint and iterate. I wanted to make sure we understood what we were building so we didn’t have to rewrite it again in six months. When you’re passionate about the direction and the work matters, I can move plenty fast. Shipping code without understanding why we’re shipping it isn’t moving fast – it’s just creating tomorrow’s technical debt.
Growth teams are fundamentally “make money” teams. That’s not a judgment – companies need revenue to exist. But there’s a difference between knowing intellectually that your job is to optimize conversion funnels and spending your days A/B testing whether a green or blue button gets 0.3% more clicks. Watching how that particular sausage gets made was… illuminating.
The tech stack: this 12-year-old Ruby monolith had my brand new M4 MacBook with 32GB of RAM running out of memory because of webpack. I had to restart services multiple times a day just to keep developing. Not because I was doing anything fancy – just normal development work. The developer experience team was doing their best with what they had (genuinely heroic efforts), but you can only polish a monolith so much.
Lessons Learned (Or: How I Learned to Stop Worrying and Love the Mismatch)
Your interview skills need to level up beyond asking good questions. I’ve always prided myself on asking thoughtful technical questions in interviews. “Tell me about your technical debt.” “What’s your deployment process?” “How do you handle on-call?” When nobody mentions ANY challenges with a 12-year-old codebase, that’s not because there aren’t any. It’s because they’ve gotten so used to them they don’t register anymore. That’s information you need to dig for.
Team placement can override everything else. You can believe deeply in a company’s mission – and I do think Handshake helps students find opportunities – while being completely wrong for a specific team.
Some of us are documentation people, and that’s okay. There are engineers who can ship fast and fix later. There are engineers who need to understand before they build. Neither is wrong, but if you’re the second type on a team that needs the first, everyone’s going to have a bad time.
Follow the resources. Handshake AI launched while I was there, and you could watch the talent flow toward it in real-time. When your team’s best engineers are getting pulled to the shiny new AI project and your product roadmap starts looking suspiciously empty, the writing’s on the wall. It’s not personal – it’s just where the company’s placing its bets.
What This Actually Means
After decades of building online communities and working in civic tech, I know what environments help me do my best work. Handshake wasn’t going to get that work from me, and I wasn’t going to thrive there. That’s not a failure on anyone’s part – it’s just a mismatch.
I spent my last days doing what felt right: going on coffee walks with everyone I’d worked with, making sure they knew specifically what I appreciated about them. Even when a role doesn’t work out, the people you meet matter. The early career engineers who reminded me why I love mentoring. The accessibility club folks who cared about making things better. The intern whose jokes made even the webpack crashes bearable.
Am I disappointed it didn’t work out? A little. But I’m grateful for the clarity it gave me. After this experience and watching Glitch wind down, I know exactly what I want: a role that values thoughtfulness, gives space for creativity and collaboration, and ideally doesn’t involve webpack.
Sometimes the best career moves are the ones that teach you where not to go next.
P.S. – To my former teammates: you’re doing incredible work, and I’m rooting for you. To anyone considering Handshake: it’s a great place for a certain type of engineer. If you’re a “ship fast and iterate” person who thrives on growth metrics, you might love it. If you’re a “write documentation first” person who needs to understand the why before the how, maybe look at other teams. Happy to chat specifics if you want to reach out.