Ryder Kemper was in Ohio, winding down a startup he and his college friends had built together. The team had decided to close it — not because it failed, but because they wanted different things. Ryder knew he wanted to stay in startups, and he knew he wanted to be in San Francisco. A message on Work at a Startup from Corgi Insurance's first sales hire changed everything. He did a thirty-minute interview on a Friday, flew to SF on Sunday for a work trial, and never went back. "By the time I had an offer, I had already helped to get the signature Costco mattresses into the house we were living in."
Corgi Insurance (YC S24) is rebuilding core financial infrastructure from the ground up — insurance systems, policy administration, claims — with the goal of owning the stack end to end.
The Mystery Machine test
Ryder's work trial was not a whiteboard exercise. He spent roughly half his time writing code and the other half riding in the company's Mystery Machine bus, hauling furniture to a new office. That ratio told him something important about the kind of place Corgi was. "The energy was just different. I felt like there was a good chance of success but worst case scenario it would be a great time."
He calls himself employee number seven. His self-assigned title: Chief Furniture Mover.
What he actually builds
Ryder has touched nearly every part of Corgi's technical stack:
- Core policy administration and claims systems
- New product development as Corgi launches additional insurance lines
- Hiring processes for new engineers and teams
The claims system is the project he talks about most. Working closely with adjusters who "think its all magic and crazy how fast we can put stuff together," he gets fast, enthusiastic feedback that makes the next iteration easier to ship. The loop is tight: build, get it live — sometimes before it feels fully ready — then iterate on real feedback from customers and the sales team.
His current tool of choice is Claude Code. He recently set up a desktop at home he can shell into remotely, letting his AI agents run even when his laptop is offline. One trick he likes: having Claude generate artifacts beyond terminal output — diagrams in Figma, recorded videos of pull-request work — to make its output more understandable to the rest of the team.
Why the people matter
"The concentration of talent here is really crazy," Ryder says. What stands out to him is the default posture: no idea is too big, no challenge gets waved off. "The default answer is always 'yea we can do that,' or 'why don't we just do it ourselves.'" The founders give people real freedom to operate, and Ryder says he has learned a lot about business just by watching how they navigate situations nobody on the team has seen before.
He also notes, with equal sincerity, that he was surprised by how much milk co-founder Nico can drink.
Two years, ten years of work
Ryder estimates he has packed about ten years' worth of experience into roughly two. He has shifted between building, managing, and scoping new projects, but has stayed close to whatever Corgi is working on next. "To me everything still feels like a new startup." He has also discovered something unexpected about himself: he is happier with less stuff. Moving around frequently for work, he stopped accumulating things and found he didn't miss them.
He plans to start his own company one day. For now, Corgi is the place where he is learning how.
Who would thrive here
If you want clear boundaries and a narrow job description, this is not the role. If you want to ship fast, own entire projects end to end, and do whatever needs doing — engineering or otherwise — Ryder's advice is simple: "Expect a lot of uncertainty but also a crazy journey that has not really been matched by anything else in my experience. Expect to work extremely hard and constantly feel like there's never enough time for anything. Expect to learn a lot about yourself and make a new group of close friends."
Corgi Insurance is hiring. You can find them on Work at a Startup.