Meet Our New CEO: Sam Gilliland

Posted by on August 02, 2018


Sam GillilandWe are excited to introduce our new Chief Executive Officer of Cherwell Software, Sam Gilliland, today. With a customer-focused mindset and community-oriented approach, Sam joins us with a deep understanding of how technology can improve business processes. I was pleased to have the opportunity to ask him a few questions. Read on for more.


Q: What brought you to Cherwell?

A: I have been in enterprise technology for essentially my entire career and have been a customer of service management software as a leader in an organization. I’ve seen the incredible benefits of well executed automation to fuel transformation within companies as they ride a wave of growth. These are reasons why the space is so interesting to me. Cherwell itself is in a phenomenal position as an emerging leader in the evolving segment—as service management expands from IT to enterprise-wide—with tremendous fundamentals. Cherwell has great technology and has built a culture aligned to a set of values that I share: heart, hunger, humility and honesty. Obviously, I’m just getting to know folks beyond the founders and the leadership team; however, the importance that is placed on maintaining strong customer relationships, respect for individuals, and a commitment to service are all part of the reputation that precedes them.  

Q: What has been a key focus of your career?

A: Besides working in and around technology businesses, in any job I’ve had, I’ve kept my focus on staying close to the customer. I do this by monitoring feedback at every step as a continuous part of the customer relationship. As I mentioned, a customer-value focused organization was one of the prime aspects that attracted me to Cherwell Software. There is a level of service that is really unmatched in the space.  

Q: What is your leadership style?

A: As a leader, I believe it is my job to provide direction and strengthen the organization to build on itself. I am focused on driving individual successes for teams through creating effective pathways and removing obstacles. It’s my job to provide vision and clear the path for success.

Q: How did you get into technology?

A: My college roommate and I started a software business while studying electrical engineering at the University of Kansas. You might say we were pioneers of the personal computer age, as we found ourselves working with engineers at IBM and Microsoft debugging early versions of their hardware and software. That business ultimately didn’t pay for the groceries, so when I graduated I went to work for Lockheed Missiles and Space in Austin, Texas, developing hardware and software for land and air based defense systems. When I got the opportunity to work for Sabre, I jumped on board. I spent several years coding before I moved into management roles and my perspective on technology broadened even further. I saw the power technology offers and the value particularly of specialized, digital tools to organizations and, ultimately, to consumers. So, it all came full circle.

Q: What did you do at Sabre?

A: Well, as I mentioned, I started as an engineer—coding. After some time doing that, I started to move into different types of roles in technology, sales, and marketing. At different points I served as executive vice president and chief marketing officer of Sabre, group president of Sabre Airline Solutions, and CEO of, a division of Sabre. Ultimately, for nearly 10 years, I served as chairman and CEO of Sabre.

Q: What have you been doing since you left Sabre?

A: Most recently, I’ve been working as a senior advisor to an investment firm, Dimensional Fund Advisors, helping them scale their rapidly growing business. Outside of that, I can’t escape my love of tech, as an example serving as executive partner at Siris Capital Group, a technology-focused private equity firm. I also served on a number of public and private company boards.

Q: We hear you used to swim competitively? Do you still?

A: Oh boy, I can’t believe you dug that up! Yes, I was a competitive swimmer and water polo player through high school, and played water polo my first year in college. I found it to be incredibly valuable in developing discipline, determination, and perseverance. The early morning practices were a bit grueling, and during the summers, we were typically in the water about five hours a day. It was a great experience, and I believe it contributed to my development as a leader. I still put on the goggles several mornings a week, but—these days—around water I must say I prefer a fishing pole to goggles!

Check out our announcement in our Newsroom. Welcome to the Cherwell family, Sam!