A Frontline Fridays conversation with David Dawson, VP of Retail and Digital Technology, Pilot Company
TL;DR
Pilot Company operates more than 900 travel centers that never close. For David Dawson, VP of Retail and Digital Technology, that constraint has shaped a technology philosophy built on one principle: if frontline teams are expected to show up for guests 24 hours a day, the tools they rely on have to show up for them too.
In a conversation with Frontline Fridays host Ron Thurston, David shares why simplicity is a discipline, not a default, why the best technology decisions get made closest to the work, and what happens when corporate teams actually spend time on the floor.
Three key takeaways:
- Technology that doesn’t simplify the job makes it harder. Complexity is a leadership failure.
- You cannot build effective frontline tools from a corporate office. Proximity to the work is non-negotiable.
- AI is most valuable on the frontline when it removes friction, not when it adds features.
What is frontline technology in retail?
Frontline technology is the set of tools, systems, and platforms that store associates, store managers, and field teams rely on to run daily operations. In multi-location retail, it covers point-of-sale, task management, internal communications, mobile learning, and the integrations that connect those tools to the wider tech stack.
The shift over the last five years has been from desktop-based, back-office systems to mobile-first platforms designed for the shop floor. The goal is the same in every case: keep store leadership in front of guests and teams, not behind a computer.

The store that never closes
Most retailers get to close their doors at night. Their systems get to reboot. Their teams get to reset.
Pilot Company does not.
With more than 900 travel centers open around the clock, Pilot serves professional truck drivers, RV travellers, and commuters across 46 states and five Canadian provinces. The operation never pauses. Which means the technology powering it cannot either.
David Dawson has spent nearly 25 years building the systems that keep Pilot running: point-of-sale, payment processing, task management, and the digital tools that help cashiers, maintenance teams, and store managers deliver for guests at every hour of every day.
His perspective is grounded and practical. Technology is not a product. It is infrastructure. And when it fails the frontline, the people paying the price are the ones already doing the hardest jobs.
That belief shapes everything about how David’s team works. And it starts, perhaps surprisingly, with getting out of the office.

How do you build retail technology that actually works for store teams?
Most corporate technology teams build from assumptions. David’s team builds from evidence.
The IT Road Trip program at Pilot is exactly what it sounds like. David loads his technology team into a 15-passenger van, drives out from their base in Knoxville, Tennessee, and visits as many stores as they can reach. No agenda. No presentations. Just time in the stores, working alongside the people who use the systems every day.
The impact is consistent and immediate.
“You almost always see their perspective and their behavior change when they come back from those types of trips. They then think differently about the work that they do. They're much more conscientious about the impact that they have.”
David Dawson, VP of Retail and Digital Technology, Pilot Company
What changes is not just awareness. It is instinct. Engineers who have fronted a cooler, restocked a shelf, or watched a cashier navigate a POS system mid-rush develop a different standard for what the technology they build has to do. They stop optimising for what looks good in a demo and start optimising for what works at 3am on a busy interstate.
David asks visiting corporate staff to front the cooler as a matter of habit: to face every bottle in the cold case so the labels are visible. It is a small, unglamorous task. But it teaches something no dashboard can.
“These are the things that our frontline has to do all day every day in a 24-hour business. A 24-seven business never stops. These are the types of small things you have to do that make a big difference.”
David Dawson, VP of Retail and Digital Technology, Pilot Company
So what: For any organisation building tools for frontline teams, proximity to the work is not optional. Leaders who design systems without regularly using them build systems that serve themselves, not the people on the floor. This is the same operational principle that drives the best area manager store visit programs: closer proximity, better decisions.

Why simplicity is a discipline, not a default
David’s mantra is three words: simplify, simplify, simplify. He said it on stage at NRF. He repeats it inside his team constantly. And the reason he has to keep repeating it reveals something important about how technology organisations tend to drift.
The pull toward complexity is real. When you are deep in a problem, building a sophisticated solution feels like progress. It often is not.
Pilot learned this directly. Several years ago, David’s team built a deli management system for their food production operations. It was technically impressive. It was also, as the store teams put it, like a rocket ship.
“They said that thing is like a rocket ship. I need an advanced degree in astrophysics to use this thing. All I really needed was a camera and a monitor so I could see what's happening on the deli while I'm back in the kitchen.”
David Dawson, VP of Retail and Digital Technology, Pilot Company
The team had spent significant time and resource building something that overshot what the stores actually needed. The real solution was simpler than anything they had designed. And they only found that out by going to the stores.
This is a pattern David has observed repeatedly. Technology teams get excited about capability. Frontline teams need usability. The gap between those two things is where most enterprise technology fails.
The standard David holds his team to is direct: if a new tool does not make the job easier or better, it is not progress. It is a step backwards.
So what: Complexity in frontline technology is not a sign of ambition. It is a sign that the team building the tool has not spent enough time with the team using it. The discipline of simplicity has to be actively maintained, not assumed. The same principle applies to retail audit software selection: tools that overshoot the user’s actual job get abandoned by the frontline.

What does 24/7 retail technology require?
A 24-7 retail operation runs continuously, with no scheduled downtime, no nightly system reboots, and no break in customer service. For technology teams, that means every tool deployed has to operate across calendar-day boundaries, sync without interrupting active transactions, and remain reliable at every hour, including the small hours when support teams are not on shift.
Running a business that never closes sounds like an operational challenge. It is also a technology one.
David describes what most retail operators never have to consider: transactions that span two calendar days. Systems that cannot be rebooted. Routines that have to run continuously without a convenient window to reset or update.
For Pilot, the shift from paper-based operations to digital has been transformational. Store managers used to carry clipboards. Compliance checks happened on paper. Process guidance lived in binders stacked on shelves.
Today, those routines are digitised. Using YOOBIC as a task management platform, Pilot has moved its workforce off the back office and onto the floor. Managers who previously had to sit at a computer to complete administrative tasks can now do that work on a handheld device while they are serving guests.
“We love to see our managers out on the sales floor, having those human interactions, helping with transactions. That's where we really want the management, the leadership in the store to be, not back in the back office doing paperwork.”
David Dawson, VP of Retail and Digital Technology, Pilot Company
The operational implication is significant. In a 24-7 environment, any tool that pulls leaders off the floor is a cost. Any tool that keeps them on it is an investment. This is the same operational logic behind why retailers are digitizing store visit procedures: time recovered on the floor compounds across every shift, every store, every quarter.
AI is extending this further. David’s team is using AI to help frontline workers access information and resolve problems in real time, from troubleshooting a faulty freezer to finding the right process card without digging through binders. The goal is not automation for its own sake. It is removing the friction that slows teams down when every hour matters.
So what: The value of technology in a never-closing operation is measured in minutes, not features. Every time a manager spends less time searching for information or completing back-office tasks, that time moves to the floor, to guests, and to the team. That is the return.

The human behind the counter
Pilot’s business case is well understood: fuel, food, showers, rest stops. What is less visible is the human infrastructure that holds it together.
David describes something that reframes what frontline service means at Pilot. For a professional truck driver on a long-haul route, a Pilot cashier may be one of only one or two human interactions they have in a whole day. The other is usually a loading dock.
That is not a customer service insight. It is a human one.
“We don't take that lightly. We understand the significance of those human interactions. We understand that life on the road can be a challenge. So we try to be there for them.”
David Dawson, VP of Retail and Digital Technology, Pilot Company
It also creates a real operational challenge. Frontline teams at Pilot have to read the room quickly. Some guests need to get fuel, use the bathroom, and get back on the road. Every minute they are not driving is a minute they are not earning. Others are on a mandated break, legally unable to drive, and genuinely need the time and the human contact.
Recognising the difference is not just good service. It is the job. And it is a skill that cannot be automated.
This is where technology and leadership intersect. The role of the tool is to remove everything that gets in the way of that human interaction. The role of the leader is to make sure their team understands why it matters.
So what: Frontline technology that frees up time for human interaction is not just operationally efficient. In businesses like Pilot, it is the whole point. The tools that matter most are the ones that give people on the floor more capacity to be present with the people in front of them. This is the same dynamic behind employee engagement in retail: connectivity makes recognition possible, and recognition is what tells frontline teams the work matters.

Why field experience is not optional for retail tech leaders
Field experience for retail tech leaders is the requirement that anyone building or deploying technology for stores has direct, recurring exposure to the operational realities those stores face. At Pilot Company, that means almost all field leadership has come up through the stores. External hires brought into division-level roles are sent back to run a single store first. The principle is structural: closer proximity to the work produces better decisions about the work.
David is candid about his own position in this. As someone who has spent his career in technology, he does not carry the same credibility on store operations that his field leadership counterparts do. He has earned a different kind of credibility, through the IT Road Trip, through the relationships his team builds with store staff, and through the discipline of listening before building.
“As someone who spent my life in the office working on technology, you can't just plop me into a field leadership position and expect that I'm going to know how to run a region of stores. You have to start from being on the front lines.”
David Dawson, VP of Retail and Digital Technology, Pilot Company
The implication for technology leadership is clear. If you want your team to build tools that work for the frontline, you need people who understand the frontline. Not from a requirements document. From experience.
So what: Organisations that separate their technology teams from their store teams build tools for the wrong problem. Closing that gap is not a cultural nice-to-have. It is a product requirement.
The standard that matters
David Dawson’s philosophy is not complicated. It is just consistently applied.
If the technology makes the job easier, it is doing its job. If it does not, it is getting in the way. And the only way to know which one is true is to spend time with the people using it.
In an industry that tends to celebrate innovation for its own sake, that is a more demanding standard than it looks. It requires technology leaders to stay close to the work, resist complexity, and measure success by what happens on the floor rather than what looked good in the build.
For Pilot, with 900 locations open every hour of every day, there is no room for tools that slow teams down. The frontline does not get a reset. The technology it relies on cannot afford one either.
Key takeaways
- Proximity to the work is the foundation of good frontline technology. You cannot build effective tools from a corporate office. David’s IT Road Trip program exists because there is no substitute for seeing the job firsthand.
- Simplicity is a discipline that has to be actively maintained. The pull toward complexity is constant. The deli management story is a reminder that impressive technology and useful technology are not the same thing.
- In a 24-7 operation, technology is measured in time recovered, not features delivered. Every minute a manager spends off the floor is a cost. Tools that put leadership back in front of guests and teams deliver the real return.
- The human value of frontline work cannot be automated. For many Pilot guests, a cashier interaction is one of their only human connections all day. Technology that frees up space for that interaction is not just efficient. It is meaningful.
- Field experience is a prerequisite, not a preference. Pilot’s insistence on field leadership coming from the frontline is a structural decision that keeps the organisation grounded in operational reality.
See how leading retailers turn frontline technology into store performance
YOOBIC helps retailers like Pilot Company, Michaels, and Hugo Boss strip administrative load off store managers, simplify the tools their teams use every day, and keep leadership on the floor where it matters most. Book a demo to see how it works in your store network.
Frequently asked questions
How do retailers digitize store operations without disrupting the frontline?
The most successful digitizations replace paper-based, back-office routines with mobile-first workflows that store managers can complete on the floor. Pilot Company moved compliance checks, task management, and process guidance from clipboards and binders to a handheld platform, which kept managers in front of guests rather than behind a computer. The principle is that any tool pulling leadership off the floor is a cost, and any tool keeping them on it is an investment.




