A Personal Update: New Role, Same Focus

About a month ago, I started a new role as a Principal Engineer at North. On paper, it might look like a big shift after spending the past eight years in leadership. But looking at my whole career, it feels like a natural next chapter, and one I’m extremely excited about.

I’ve been lucky to work across a wide range of roles and organizations in software development. I’ve been a contractor, built businesses where I had to wear every hat, worked at startups before market fit, led teams as companies scaled from a dozen people to hundreds, and helped run large-scale services.

For the past eight years—first at TaxJar, then at Recharge—I’ve been in engineering leadership, managing groups of four or five teams at a time. I stayed close to the architecture and the work itself, collaborating with incredibly smart people on both the technical and organizational sides. I’m deeply grateful for those experiences, for everything we built, and for the people I had the privilege to work alongside. Those years gave me invaluable vantage points across the technical and human sides of building software, and that breadth has shaped how I approach my work today.

In my early career, my focus was on understanding and iterating on how to build. In recent years, it’s been about scaling platforms, teams, and companies. That meant balancing architecture and process, and it also meant making time to keep building and learning on my own.

After five years at Recharge, an opportunity came along that I couldn’t pass up: joining North. The team is young and hungry, the space is exciting, and the stack gives me room to dive deeper into cloud services—even after 15 years of using AWS—as well as write Python every day (we’ll see if it can tempt me away from my 20-year love affair with Ruby!).

I’ll admit, the idea of shifting back into an individual contributor role gave me pause at first. I love to build software—it’s my livelihood and my hobby—but I also thought about how it might look on a résumé. Then I zoomed out. My career has always been about software, continuous learning, and bringing experience into new environments where I can keep learning and doing. Viewed that way, this move made perfect sense.

That bigger picture also includes my work outside North. I’m still building Looping, my long-term side project, and I’m available for advising on a very limited basis. I also keep reading, thinking, and writing about leadership and engineering topics—things that continue to shape how I work and how I help others grow.

After being in software professionally for more than half my life, I’ve learned that every career path is its own mix of choices, timing, and luck. Leaving after five great years wasn’t a decision I made lightly, but this opportunity brought the right mix of challenge and growth to make the leap worth it.