We are proud to profile a number of our team members spearheading growth and innovation at Roundtrip. Check out the rest of the series to meet our entire leadership team.
Brian Ryther is the Chief Technology Officer at Roundtrip. Brian has over 20 years of experience in working in and leading software engineering teams. During his career, Brian has worked in a variety of industries – including government, finance and associations, and healthcare. His experience ranges from consulting engagements to leadership positions within Fortune 500 companies. Brian is passionate about building great products through empowered engineering teams. Some of Brian’s most proud accomplishments include the complete redesign and migration of cancer.org and the digital transformation of a complex insurance offering through automated underwriting outcomes via web portals and API.
What project at Roundtrip are you most proud of?
My proudest accomplishment isn’t a single project — though we’ve shipped some things I’m genuinely excited about. What I’m most proud of is the operational and cultural foundation we’ve built over the past several years. For an engineering team to do its best work, you have to invest in the unglamorous stuff first: the tooling, the release processes, the testing infrastructure, the feedback loops. We did that work, and the payoff has been real.
Beyond the mechanics, we’ve built a culture of trust and autonomy where engineers feel empowered to make decisions and move quickly. That combination — solid operational practices and a team that genuinely owns the outcome — is what allows us to do ambitious things.
What mentor or prominent figure has influenced you in your career and why? You can share more than one.
Honestly, my biggest career lesson is that I don’t need to have all the answers — and more importantly, that nobody expects me to. That sounds simple, but early in my transition to management I had a hard time with it. I kept trying to be the one with the direction, the decision, the plan. I made a lot of mistakes before some really talented people helped me understand what leadership actually looks like.
Today, I genuinely try to take something from every conversation I’m in — from the most junior engineer on the team to the CEO. That mindset has been shaped by a lot of mentors and peers over the years rather than any single person. I know that’s not really answering the question — but it’s the most honest answer I have.
Can you share some of your favorite books?
I read a lot of technical and leadership books, which I’ll admit sounds boring at dinner parties. But “Accelerate” by Dr. Nicole Forsgren is one I’d press into the hands of any engineering leader. The research-backed principles in that book are as relevant today as ever — maybe more so given how much our field has changed.
Outside of the technical shelf: The lessons from “The Mamba Mentality” by Kobe Bryant stuck with me. Kobe’s obsession with craft and the specificity of how he thought about improvement — it translates way beyond basketball.
What future do you envision for your team at Roundtrip in the next two years?
The foundation work we’ve been doing for the past few years is really starting to compound. We’ve got a talented group of engineers who care deeply about the people we serve, and the investments we’ve made in our architecture and platform have created real runway to do ambitious things.
Over the next two years, I want this team to be known for two things: speed and reliability. Not speed at the expense of quality, but the kind of velocity that comes from getting the fundamentals right. Transportation is a solvable problem, and I believe Roundtrip can build the platform that proves it.
Tell me about your hobbies and things you enjoy doing in your free time.
Sports are a big part of how I recharge. I love playing golf, basketball and volleyball. There’s something about competing and moving that clears the head in a way nothing else does. But honestly, my real life’s work is being a husband and father to my two boys. That’s the job I take most seriously.
If you could donate $1 million to any organization, which would it be?
The American Cancer Society, without question. Cancer took my father too soon and fighting it has been something close to my heart ever since. I’ve had the privilege to work with the team at ACS a few different times in my career across a few different initiatives. Each time I’ve come away very impressed at their team’s commitment to their mission and focus on the people they serve.
It’s very rewarding to work with ACS’s Road to Recovery program here at Roundtrip. The people volunteering their time in that program is proof – you don’t need a million dollars to make an impact on people’s lives!