Flexport head of trucking: New broker tech will be crucial in 5-10 years

“As Flexport grew, it was very fragmented – very customer-centric – but on the off side often quite fragmented,” Driegert said. “So coming on board as the trucking expert [and] ground freight expert, there’s a significant opportunity to drive systems improvements and just consolidate a lot of how we do procurement and operations on that side.”

Before starting at Flexport, Driegert helped build Uber Freight. Fuller asked why he left Uber for Flexport.

“I still have a lot of attachment to what we built at Uber Freight. It was a great team and I think they have a great product,” Driegert said. “The journey of that company definitely shifted when we did the Transplace acquisition. As a company, it was evolving and going in a very different direction than we initially set out [for].”

He said that the original journey for Uber Freight was a vision of digital freight management and how the back end can be automated with new technology to drive an automated freight broker. Then-Flexport CEO Dave Clark reached out to Driegert around that time, offering the opportunity to take that same idea and apply it internationally within the context of a global forwarder.

“It was very compelling,” Driegert said. “I was very compelled by Flexport as a technology company, and it was a very unique opportunity to learn new things and build a whole new type of capability … . That was the big motivating factor initially.”

Flexport purchased Convoy shortly after the Seattle-based digital brokerage shut down in late 2023. Fuller asked Driegert how that deal came to be. While Driegert couldn’t give many details about the deal, he did explain why Convoy was worth the reboot.

“Ultimately, it made a lot of sense if you look at it holistically,” Driegert said. “The Convoy team, mainly in Seattle – we had a strong team in Seattle – if you look at that team, there’s a lot of resume overlaps. There’s a lot of cultural affinity. We are a tech company [and] it was clear to that team that this would be a safe place to land. Of course, my background with Uber Freight [added] a lot of familiarity. That was just one of these amazing alignments of the stars.”

He added that it was always Flexport’s vision and intent to bring Convoy back and build a viable business around it.

“I do fundamentally believe in the model, and I believe in the technology,” Driegert said. “In five years to 10 years from now, every broker will look like Convoy or Uber Freight. I fundamentally believe that. I believe the tech that has been introduced to the market will change the market, and that is driving a trend.”

While acknowledging that the freight market isn’t fast-moving due to slow adoption of new technology, Driegert said a surge of AI and technology companies in the space has created a “rapid democratization of what was built at Convoy and Uber Freight.”

Driven by the COVID-19 pandemic, there is an increasing focus by brokers on reducing operating expenses, he said.

“To get that down, you either need to outsource or you need to leverage technology intelligently,” Driegert said. “I think there’s a lot of solutions out there now that allow for the leveraging of technology to lower the carrier sourcing cost … . I don’t think a broker will be able to compete without an [operating expense] that is significantly more competitive than it has been over time. And I think those brokers that are able to embrace tech, outsourcing, a combination thereof [and] restructure their processes where they can get their procurement processes to a level of automation equivalent to what an Uber or Convoy were able to achieve, I think you won’t be able to compete in 10 years if you aren’t in that position.”