Why I Joined Pylon to Lead Product

I didn’t plan to leave venture. I definitely didn’t plan to spend the next seven years building in the trenches of regulated infrastructure. But somewhere along the way, building deep in the stack, I realized that’s where the real opportunity lives. Now, I’m doubling down—joining Pylon as VP of Product to help rewire how mortgage works, from the ground up.

Mortgage, like insurance, is stuck in an expensive maze of intermediaries and legacy software. The result is a process that’s slow for borrowers, painful for originators, and wildly expensive for everyone. We’ve seen 20 years of incrementalism—companies tackling one small piece of the puzzle and stitching them together—only to find out you often have to bend the puzzle pieces to make them fit.

Pylon isn’t here to polish the surface. We’re rebuilding the infrastructure beneath it. The vision is a vertically integrated, programmatic platform that transforms mortgage from a manual factory into an intelligent system—software that handles credit, compliance, capital, and customer experience from application to loan settlement. Just like Stripe did for payments, Pylon is making mortgages programmable.

That kind of bold, full-stack ambition is rare. But more than the market, more than the thesis—it was the people that made this an easy “yes.”

I’ve known Trent, Pylon’s founder, for nearly a decade. We kept crossing paths while I was working at Vouch and back in my VC days. One of our board members at Pylon was my first manager in venture. These are people I’ve trusted and learned from for years—and the broader Pylon team is one of the most impressive I’ve seen: alumni from Stripe, Better, Affirm, and other companies that actually moved the needle in broken industries.

Before Pylon, I spent over six years at Vouch, a commercial insurance startup I’d initially backed as an investor. I joined thinking it’d be a short detour. It turned into a deep dive—because once you’re inside a system like insurance or mortgage, you can’t unsee how broken the mechanics are. And if you like fixing things, it’s hard to walk away.

At Vouch, I helped launch new products, scale the platform, and lead teams across APIs, pricing tools, and AI-native insurance. But what I really learned is that in regulated industries, the real product is the messy middle. The most meaningful work often wasn’t a spec or a UI—it was rethinking how funds move, how risk is priced, or how to collaborate with regulators. The most important changes weren’t always visible, but they made everything else possible.

That’s the mindset I’m bringing to Pylon. Because the opportunity here is just as foundational—and the problems just as urgent. As I thought about what to build next, one thing kept coming back to me: “A problem this foundational doesn’t need incremental fixes. It deserves a big swing.”

That’s what we’re taking here at Pylon. And I’m thrilled to help lead that effort.

Let’s go build.