SHOW NOTES
Great technology doesn’t announce itself. It just makes the job easier.
In a business that never closes, that’s not a nice-to-have. It’s the whole point.
In this episode of FRONTLINE FRIDAYS, host Ron Thurston sits down with David Dawson, VP of Retail and Digital Technology at Pilot Company, to explore what it really takes to build technology that serves the frontline — and the leadership philosophy behind it.
With 900+ travel centers open around the clock, Pilot runs one of the most operationally complex retail environments in the country. David leads the teams responsible for the systems that keep it all running: point-of-sale, payment processing, task management, and digital tools that help cashiers, maintenance teams, and store managers deliver for guests every hour of every day.
David explains why 24-7 operations demand a different kind of technology thinking — one where reliability, simplicity, and usability aren’t features but requirements. He shares how digitizing paper-based routines has mobilized Pilot’s workforce, freeing managers from back-office tasks and putting them back on the floor with guests. And he talks about how AI is changing the way frontline teams access information, solve problems in the moment, and improve productivity without adding headcount.
But the episode isn’t just about technology. It’s about what happens when you understand the humans on the other side of it.
David and Ron discuss what it means that a Pilot cashier may be one of only one or two human interactions a long-haul truck driver has in a whole day — and what that asks of the people behind the counter and the leaders who support them. They explore why field experience is irreplaceable, why the best tech leaders spend time on the floor, and what David’s IT Road Trip program has revealed about the gap between building tools in a corporate office and using them in a travel center at 3am.
His mantra: simplify, simplify, simplify. Not because the work is simple — but because complexity is a failure of leadership.
If you lead teams, build tools, or make decisions that affect people on the frontline, this conversation will change how you think about all three.
What you’ll learn in this episode:
- (02:13) What Pilot is, how it operates, and why it matters to American commerce
- (04:22) Why a Pilot cashier may be one of only one or two human interactions a truck driver has all day
- (05:41) What it means to lead 26,000 frontline team members in a 24-7 environment
- (07:27) The pride, passion, and ownership mentality of Pilot’s frontline teams
- (09:04) Why David’s technology team exists: to serve the systems that serve the stores
- (11:26) The IT Road Trip program: loading tech teams into vans and driving to stores
- (13:30) The unique technology challenge of running a 24-7 operation
- (15:53) How YOOBIC task management has automated routines and mobilised Pilot’s workforce
- (17:39) How AI is helping frontline teams access information and solve problems in real time
- (19:52) Simplify, simplify, simplify: David’s mantra from NRF and why it has to be repeated
- (22:02) The balancing act between efficiency and human connection for truck drivers
- (23:35) Why Pilot’s field leaders almost always come from the frontline
- (25:18) David’s message to Pilot’s frontline teams: appreciation, feedback, and keeping the loop open
GUEST BIO
David Dawson is Vice President of Retail and Digital Technology at Pilot, but his career started where many frontline workers begin—on the helpdesk, supporting stores that never close. For almost 25 years, David has worked his way through technology roles focused on one core belief: if people are expected to show up for customers 24/7/365, the tools they rely on have to show up for them too.
Throughout his career, David has built and led technology that supports store managers, cashiers, maintenance teams, and other frontline team members—from point‑of‑sale and payment systems to task management, communication platforms, and digital tools that serve guests. He understands firsthand that unreliable or poorly designed technology doesn’t just slow a business down—it makes a hard job harder.
Today, David leads the teams responsible for enabling frontline execution across Pilot’s 800+ travel centers, with a focus on reliability, simplicity, and real‑world usability. His goal is to make sure technology works for the people in stores, not the other way around—so teams can focus on what matters most: serving guests and keeping operations running smoothly, every hour of every day.
David holds an MBA from the University of Tennessee’s Haslam College of Business and a BA in Business Administration from Maryville College.
ABOUT FRONTLINE FRIDAYS
Your store teams feel it: more pressure, more change, less time to get it right. FRONTLINE FRIDAYS helps you turn that pressure into impact.
Built for senior retail + hospitality field leaders, each episode features candid conversations with execs from iconic brands, sharing tactics you can use today.
HOSTED BY RON THURSTON. Ron is a global retail leadership expert and two-time bestselling author of RETAIL PRIDE (2020) and HUMAN PRIDE (2025).