Freight technology rarely advances in a straight line. It is pulled simultaneously by market forces, regulatory developments, and the gradual pace of digital adoption across the industry.

Thomas Wasson, host of FreightWaves' Loaded and Rolling podcast, spoke with Sean Dehan, vice president of strategy and corporate development at Truckstop, about how those converging pressures have reshaped the freight industry's approach to combating fraud.

Truckstop, founded in 1995 and headquartered in New Plymouth, Idaho, operates one of the largest digital freight matching platforms in North America alongside DAT Freight & Analytics, giving its strategic decisions broad influence across the brokerage and carrier ecosystem.

Dehan joined Truckstop just over four years ago, during a period he now recognizes as a defining era for trucking. Industry veterans have described the last few years as the worst freight recession in their lifetimes.

"I guess I'm proud to have made that one my first," Dehan said.

At Truckstop, Dehan's responsibilities extend beyond the day-to-day product roadmap.

"I help guide the company on where to invest, where to go, what to build next, where to grow next, how to expand our services for our customers," Dehan said. His mandate spans product development, partnerships, and potential acquisitions, giving him a broad perspective on both Truckstop's strategic direction and wider industry trends.

A Carrier-First Philosophy

Truckstop's guiding philosophy has always placed the carrier at the center, according to Dehan.

"Truckstop has always been a company that focuses on the carrier first," he said. "We believe we can serve our brokerage customers best if we serve our carrier customers best and first as well."

That carrier-first orientation is baked into the structure of a two-sided marketplace.

"When we build for one side, it typically works for both sides and typically improves both sides," Dehan said.

However, Dehan believes the era of one-size-fits-all tooling is coming to an end. The carrier population encompasses vastly different operational realities. A dry van operation and a flatbed hauler moving oversized machinery face fundamentally different challenges and priorities.

"They might be driving the same tractor with the same engine, but the trailer they're pulling and the type of freight they're pulling is all very, very different," Dehan said. That diversity is driving a strategic pivot. "We're really focused on building products and tooling that enable carriers to build the business that they want to build and work with the customers that they want to work with," he said.

Digital Adoption's Double Edge

The industry's embrace of digital technology took on a different complexion once bad actors learned to exploit it.

"Digital adoption can drive a lot of great things, but it can also come with a lot of new challenges," Dehan said. "AI will bring a lot of amazing things, but it will bring a lot of dark things, too."

He traced the surge in fraud back to the freight brokerage boom of roughly 2010 to 2022, when growth-driven brokers demanded frictionless onboarding to assemble the largest possible carrier networks.

"If you're providing me with the onboarding solution, I need you to keep that as low friction as possible," Dehan explained. That appetite for scale carried an implicit tolerance for risk.

"The fraud that was occurring on the sidelines was just a part of the industry. It was an accepted consequence of running the business," he said.

The pandemic accelerated the problem as new entrants entered the market with minimal scrutiny.

"A lot of them were probably fake carriers," Dehan said. "A lot of them were shell companies. As the market dropped, obviously, the fraud continued and got worse."

A Permanent Shift in Broker Behavior

The compounding effects of fraud have permanently altered how brokers operate, Dehan noted.

"Even though we're in this market right now, which is by all accounts tight on a capacity basis, our brokers aren't really loosening their standards," Dehan said. "They're not changing how they procure capacity. They're just learning how to procure capacity differently than they used to."

The legal environment has intensified the pressure. Dehan pointed to the Montgomery ruling and a subsequent Texas decision he described as potentially even more consequential — both of which are pushing brokers toward stricter, more defensible carrier-selection processes. The Montgomery case underscored that brokers can face significant legal liability when carriers they select cause harm, raising the stakes for onboarding procedures that had previously been treated as routine.

"The need to have very consistent standards to deliver and display a reasonable care and approach to carrier selection has probably changed some of the pendulum swing," Dehan said.

Rather than hastily layering on unvetted data sources, brokers are concentrating on fortifying their existing procedures.

"Brokers are really trying to harden their compliance with the process," Dehan said. That tightening extends to exception handling. "Logistics is basically one giant exception, or millions and trillions of giant edge cases and tiny exceptions."

Toward "Multiplayer" Carrier Evaluation

Carriers are currently evaluated largely through third-party data over which they have limited ability to provide context or corrections. Truckstop is working to change that dynamic.

"In a lot of ways when a carrier is being vetted or validated or verified, it is a single player game," Dehan said. "In some cases, the info wasn't even right. In other cases, there were good reasons for some of the anomalies that existed in their business."

Truckstop's solution, Dehan said, is a shift toward "multiplayer dynamics" in carrier evaluation — giving carriers a mechanism to explain themselves rather than passively accepting the outcome of a review. He offered a hypothetical example: a violation stemming from a broken taillight that has since been repaired.

"Carriers need to be able to say, 'We fixed that taillight issue,'" Dehan said. "That's not an issue anymore. You don't need to be worried about that out of service."

This represents an opportunity rather than an obligation, Dehan emphasized.

"If carriers want to and believe it's in their best interest to present alternative or maybe confirmatory data, we want to enable them to do that," he said.

Lessons From ELD Integration

To illustrate how industry norms evolve, Dehan recounted an early experience when he proposed integrating electronic logging device (ELD) data across Truckstop's carrier base. The Federal Motor Carrier Safety Administration's ELD mandate, which took effect in December 2017, required most interstate commercial drivers to use electronic devices to record hours-of-service compliance — generating a new stream of verifiable operational data across the carrier population.

"In my naivete, it seemed like a no brainer," he said. He was quickly educated about the resistance such integration would face. "They were very kind to me and they corrected my outside-the-walls thinking."

Over time, that resistance faded as fraud concerns and loose capacity conditions converged.

"We had a perfect storm… the integration became the norm," Dehan said.

He sees a parallel opportunity today for carriers to stay ahead of a similar shift around operational data transparency.

"Get out in front of what will likely just become a standard at some point in time. Use it as your own carrot," he said.

The Next Frontier: Mutual Accountability

When asked to define what carriers genuinely want, Dehan pushed back against the industry's conventional answer.

"I think we get distracted by the concept of broker transparency and things of that nature," he said.

Instead, he framed fairness as mutual accountability — carriers should be able to evaluate brokers with the same rigor that brokers apply to them. That, Dehan said, is Truckstop's next frontier: helping carriers identify trustworthy broker partners, rather than simply helping them survive broker-side vetting.

"How do we create a participatory ecosystem versus an obligatory ecosystem?" Dehan asked.

While there is no simple answer yet, Dehan indicated that Truckstop will have more announcements before the end of the year.