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.
Meet Sam Farmer, Roundtrip’s Chief Executive Officer
Sam Farmer is a recovering management consultant and high-growth technology leader. She joined Roundtrip as an operations leader in 2019, then moved into the CEO role in 2024. The course of Sam’s career has afforded her the opportunity to build a depth of experience across the wide breadth of business functions. She is data-driven by nature, thrives in ambiguity, and brings a curious and resourceful mindset to any challenge she’s faced with – always seeking out opportunities to combine analysis, evidence, and lived experience to drive positive outcomes. She prides herself on ability to communicate the big picture while still being well-versed in the minute details, enabling her to deliver high impact while building trust at all levels of an organization.
Sam, what project at Roundtrip have you worked on that you are most proud of?
I am deeply passionate about fostering a healthy and equitable team culture. I revamped our employee engagement model, including rolling out a formal compensation philosophy and customized total rewards statement for each team member, which created real transparency and had a great impact on our team.
However, I’m truly a data nerd at heart. I started my career at Deloitte working in the Business Intelligence and Data Warehousing practice, and I love digging in to identify patterns and help drive impact for our customers. In my early days here, I built our very first reporting dataset, and in the many years that have followed I continue to dedicate some of my time to looking for interesting trends and partnering with forward-thinking customers to use the information from Roundtrip to drive actionable outcomes for their goals. While data is just one piece of the complex healthcare puzzle, at this point the team knows well that my first response to many questions is “what does the data show?” as a jumping off point to build broader understanding.
While I spend less time writing queries in my role today, I love keeping myself immersed in what’s going on in customer data to help shape and validate our vision and priorities
What mentor or prominent figure has influenced you in your career and why? You can share more than one.
Many of my former clients from my consulting days make the shortlist of people who have had a great influence on how I approach my career. Notable folks include Nino Davi, who is an expert at developing and driving adoption of processes and frameworks in a data-driven fashion; and Shawn Heming, a CFO and jack of many trades who has seen and done so many things in his career he continues to be one of my most valuable sounding boards.
Can you share some of your favorite books?
Generally, I’m a nonfiction nerd – give me all the business and self-help books. Last year I forced myself to read some more fiction, and absolutely loved “Tomorrow, and Tomorrow, and Tomorrow” as well as “The House in the Cerulean Sea” (Shoutout to our Marketing Manager, Ellen, for the recommendation on the second one! If you ever need book recommendations, Ellen is better than any AI or app).
What future do you envision for Roundtrip in the next two years?
As we reflect back on how much the space has changed since Roundtrip was founded 10 years ago, the years ahead are full of so many exciting plans. Something that will remain core is how we partner with our customers. We’re much more than just a software company; we’re partners for life, helping overburdened teams turn transportation from a source of frustration into a strategic lever that supports achievement of broader goals. A big area of focus for us in continuous improvement of our platform and offering is the evolution from basic transparency into actionability and automation, enabling intelligent interaction with surrounding workflows and self-healing capabilities for logistical disruptions.
Tell me about your hobbies and things you enjoy doing in your free time.
I’m a hard-headed DIYer, so you can often find me tackling some sort of house project. I love to go hiking, spend time with my dog, and I recently took up running and completed my first half marathon.
If you could donate $1 million to any organization, what organization would it be?
I’m really passionate about animal rescue, especially foster-based rescue programs which pull the highest-risk animals from shelters and give them the space to decompress and be fantastic companions. I’d spread the money across a few organizations since so many of them are localized. Fun fact: when I first interviewed for a job at Roundtrip, I told our founder, Mark, that my long-term goal was to train rescue dogs to be service dogs.