Get to Know Our Leadership – Brian Ryther

Ellen Williams
headshot of Brian Ryther

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 get to know the rest of our leadership team.

Meet Brian Ryther, Roundtrip’s Chief Technical Officer


headshot of Brian Ryther

Brian Ryther 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 and the digital transformation of a complex insurance offering through automated underwriting outcomes via web portals and API.

Brian, what project at Roundtrip have you worked on that you are most proud of? 

My proudest accomplishment for the Engineering Team is not really a specific project (although we’ve had some good ones!) – but rather the operational and cultural shift that we’ve been able to achieve in the past few years. For an engineering team to be its most effective, we need to invest in ourselves – in the tooling, the processes and supporting frameworks which help us efficiently accomplish our objective for Roundtrip.  

With the support of our leadership team, we’ve invested heavily in and completely reimagined how we build, test, release and maintain our platform.  These operational objectives are underpinned by a culture of trust and working in small increments.   Together, these changes have had an incredible positive impact on how we work – both today, and into the future.

What mentor or prominent figure has influenced you in your career and why? You can share more than one. 

Probably the biggest lesson I’ve learned in my career is that I don’t know it all, I can’t know it all – and I’m not really expected to.  Early when I was transitioning to management, I made so many mistakes centered around my belief that as the leader I needed make the decision or set the direction, etc.  I’ve been fortunate work with a lot of talented mentors, peers and reports who have helped guide me to understand what it means to be a leader.  Today, I really do try to look for guidance and inspiration in most of my interactions.  I really I feel like I can learn from everyone around me – from the most junior to the CEO.  I totally didn’t answer your question, but that’s how I feel.  🙂

Can you share some of your favorite books? 

I find myself reading a lot of technical books, in an effort to learn more about how to be better (boring!).  But in all seriousness, I recommend Accelerate by Dr. Nicole Forsgren, et al to any engineering leader.  There’s not a single right way to scale technical organizations – but the principles expressed within this book are the fundamental building blocks, in my opinion. 

I also enjoyed reading The Mamba Mentality by Kobe Bryant – I find Kobe’s pursuit of greatness to be utterly fascinating, there are so many lessons to learn about the pursuit of your goals and the mindset needed to be great.  Lastly, A Promised Land by Barack Obama – the behind the scenes look he gives into the decisions and key moments of his candidacy and the presidency is really interesting.

What future do you envision for your team at Roundtrip in the next two years? 

I’m so excited about the trajectory of this team – and what I think we’ll be able to accomplish over the next two years.  We have a talented group of engineers who deeply care about the success of our company and those we serve.  The investments we’ve made in our foundation are paying off in massive ways, and we’re beginning to make some big gains in our architecture.  In short, our goal is to build the best-in-class platform which removes transportation as a barrier and beats our competition through tech enablement.  I truly believe these goals are within reach.

Tell me about your hobbies and things you enjoy doing in your free time.

I’m a big sports enthusiast – playing golf, basketball and volleyball really helps to center me.  I also am very active in my role as a husband and a father of two boys –  this is my true life’s work! 

If you could donate $1million to any organization, what organization would it be?

Fighting cancer is very important to me, as it took my father too soon – the American Cancer Society does excellent work and I would donate the money to help them fund their efforts.  Side note: it’s personally gratifying that ACS is a Roundtrip client – it’s very rewarding to know I’m helping them fulfill their mission through my role at Roundtrip.