Hi, I’m Roger Siggs — born in NAS Pensacola, Florida, sometime in the last century (GenX FTW!), which technically makes me a government-issued nerd. These days, I’m a remote-working tech leader, husband to a lovely wife, and father to three incredible sons — including Gus, who passed away from Anaplastic Ependymoma and continues to inspire how I show up for my family, my team, and the work I do.
I’m an adult with ADHD, which means my mind is a nonstop, high-velocity idea factory — ideal for chasing innovation, exploring new tools, and getting very into obscure history facts. Over the last two decades, I’ve led infrastructure and cloud architecture efforts at companies like Oracle and SimplePractice, where I’ve built and scaled systems, introduced AI features, saved millions through vendor negotiations, and most importantly, helped teams thrive in environments that value trust, transparency, and growth.
At SimplePractice, I lead the Infrastructure org (DevOps, Release Engineering, and DB Engineering), where we’ve done everything from implementing AI tools to spinning up ephemeral environments via Kubernetes for rapid development and experimentation. I bring hands-on know-how and strategic vision, but I’m most passionate about building high-performing, people-first teams. Leadership, to me, is about creating safe spaces where others can take risks, grow, and succeed — with a bit of fun and a lot of humanity along the way.
Before that, I spent almost a decade at Oracle, unifying global infrastructure, cutting cloud costs, and launching team-focused initiatives that made a real difference. I’ve even got a few patents to my name and a surprising background as a fencing instructor — because why not keep things interesting?
When I’m not deep in infrastructure or mentoring future tech leaders, I’m a walking side quest. I collect books like a dragon hoards treasure — mostly sci-fi, history, horror, and more recently LitRPG. I’m a gamer (Destiny 2 Hunter main, currently alpha-testing Marathon), a Lego architect, a calligraphy and 3D printing enthusiast, and someone who’s slowly but surely re-learning piano. I live with music constantly in the background — from throat singing to synthwave, musicals to country, and especially Coheed and Cambria.
If you’re into tech leadership, obscure facts, book hoarding, nerdy hobbies, or want to swap Destiny loadouts and weird music recs, let’s connect and build something great—or at least geek out about why Stephen King and Clive Barker are two of the coolest people on the planet