Shivam Singh

Hey, I’m Shivam. Right now I build things at Littlebird, where I joined as hire #4 in the company. It’s been 1.75 years here. I lead the client apps, mostly desktop and web, on a codebase we share with mobile. The app grew from zero to more than 10,000 daily active users, and somewhere along the way I became the guy who knows the flows and gotchas across every layer and most teams. These days I’m deep in applied AI and product engineering.

Before Littlebird I spent almost two years as employee #1 at MiddlewareHQ, a B2B engineering analytics company. I owned the web client and the Jira integration. At some point I came up with a hack that ran our whole web app inside Atlassian Jira as a plugin. When it launched, it brought in more than half of the company’s MRR at its peak. The company went from zero to more than 30 enterprise clients while I was there. I worked very hard and learned a lot. I left with good friends, founders I still meet every few months, and a sneaker habit I never planned for.

Before that came Requestly (YC W22), since acquired by BrowserStack. I interned there for six months and found out I’m more than a Python backend dev. They offered to make me employee #1. I turned it down for a stealth meeting notes startup. Not some bold master plan, just circumstances at the time. For a while I quietly filed it under mistakes.

That startup was Synth (YC S21), where I had my first full time job as a founding engineer. In 2022, before ChatGPT was a thing, we built meeting notes that worked without a bot joining the call. Think Granola, except earlier. And honestly, our transcription, audio, and notes were better. The product never made it out of stealth, so after a year I moved to MiddlewareHQ. You already read how that went. Looking back, the mistake turned out to be one of my best decisions. It taught me how to work on my own with vague, undefined problems. Steve Jobs was right, the dots only connect when you look backwards.

The panel below has the rest of the stack trace.