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Flexport announces key executive hire to run its new truckload brokerage unit


San Francisco-based freight forwarding and customs brokerage services provider Flexport is taking steps to establish a truck brokerage unit, with the hiring of a well-known executive from Uber Freight.

In an internal company memo provided to LM, Flexport CEO Dave Clark said that effective May 22, Bill Driegert will join the company as its EVP, Head of Trucking, reporting directly to Clark.

Driegert joins Flexport from San Francisco-based Uber Freight, a subsidiary of the ubiquitous, ride-sharing service Uber, whose proprietary app matches trucking companies with loads to haul, where he served as Head of Operations and Cofounder, going back to 2016. Prior to that, Driegert was Director of Planning and Innovation for Amazon, and Chief Innovation Officer for Coyote Logistics.

Clark wrote in the internal memo that Driegert’s mission in his new role will be to develop and scale Flexport’s end-to-end customer offering for trucking.

“In this role Bill and his team will own the P&L for a free-standing trucking business along with product, tech, pricing, and procurement for our global trucking services,” noted Clark. “The trucking technology team, trucking procurement team, and trucking product leads currently in the Flexport Global Operations organization will join Bill in this single-threaded business unit.”  

The top Flexport executive said Driegert is a proven innovator who is focused on moving the industry forward, citing how Driegert was a key leader and founder in the growth of two seminal companies—Coyote Logistics and Uber Freight.

“At both, he led the way digitizing freight with industry-first innovations like API pricing, instant booking, and the first carrier self-tracking app,” observed Clark. “While at Amazon Bill launched the Amazon brokerage initiative. I came to really appreciate Bill’s ability to combine technical innovation with operational excellence. He’s the right leader to simplify and expand our trucking offerings globally as a key element in delivering world class end to end solutions for our customers.” 

The memo also included comments from Driegert about his new role.

“I'm incredibly excited to be joining this world class team here at Flexport,” said Driegert. “I've spent the last 17 years focused on empowering both shippers and carriers with better technology and tools to make freight more reliable, resilient and transparent. I believe in Flexport's mission. Freight should be easy, and we can make it so. This is the best place in the world right now to push the frontier of technology globally at every step of the freight lifecycle.”

Evan Armstrong, president of Brookfield, Wisconsin-based supply chain consultancy Armstrong & Associates, told LM that Driegert has a long history in logistics and truck brokerage, especially through his most recent role with Uber Freight and experience, in terms of building digital freight brokerages.

“I guess if somebody is going to do it at Flexport, it would make sense for him to be the person, given his background,” said Driegert. “And given the fact that Flexport likes to build its own technology, too, it makes sense from those points of view. “With what is going on in the current [global] freight forwarding environment, it makes sense to focus a little bit more on the domestic market even if it is taking a hit now but not to the same extent as freight forwarding.

In order to get Flexport’s truckload brokerage operations up and running at the level needed to become a major market player, Armstrong said building up scale is a major requirement and could take a year or two before they are “in the game,” he said.

With its recent acquisition of Shopify Logistics and Deliverr, in addition to some other acquisitions it has made, Armstrong said it is likely Flexport views its entrance into truckload brokerage as a way of supporting and developing more of an integrated solution sale for its customers across myriad service offerings in between all of its operations.

“It makes sense for them and why not do it?” he said. “They probably have the money, as the company has done pretty well over the last couple years and has built up a good war chest. It also makes sense in that now that it has the domestic fulfillment operations and now, they are going to build out some real domestic transportation management capabilities.”

A Wall Street Journal report stated that prior to this development, Flexport’s truck brokerage services were delivered through separate partnerships with Seattle-based digital freight network Convoy and Nolan Transportation Group.

Earlier this month, Flexport acquired Shopify Logistics, a subsidiary of a multi-channel commerce platform, Shopify, including Deliverr, a fulfillment technology services provider, which Shopify acquired for $2.1 billion in 2022, with a key objective of this acquisition being to expand its global services into last mile and e-commerce fulfillment.

Clark called this the “last piece of the puzzle that enables us to drive technology fueled solutions across the entire product life cycle from the manufacturer’s floor, across the oceans and skies, through ports and fulfillment, and, now, right into the hands of customers.”

And he explained that a key driver for acquiring Shopify Logistics is because the shipping industry has not experienced the same technological revolution is seen across other sectors.

“I came to Flexport specifically because I know this team is changing that,” he said. “We are digitizing and evolving one of the most important parts of the world’s economy—global trade. And I believe in our teams to deliver—democratizing the supply chain for businesses of all sizes on our mission to make global trade easy for everyone.”

Ben Gordon, founder and managing partner of Palm Beach, Florida-based Cambridge Capital, and managing partner of Ben Gordon Strategic Advisors, told LM that he believes Flexport is setting up a strategy to compete with Amazon.

“This is a return of the Jedi moment, as Flexport new CEO Dave Clark prepares to fight his prior employer,” said Gordon. 

According to Armstrong & Associates’ estimates, Flexport had $3.8 billion in 2022 gross revenue and roughly $700 million in net revenue.


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About the Author

Jeff Berman's avatar
Jeff Berman
Jeff Berman is Group News Editor for Logistics Management, Modern Materials Handling, and Supply Chain Management Review and is a contributor to Robotics 24/7. Jeff works and lives in Cape Elizabeth, Maine, where he covers all aspects of the supply chain, logistics, freight transportation, and materials handling sectors on a daily basis.
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