Convoy hires former Expedia CEO as president and COO as digital freight startup tops 1k employees

Mark Okerstrom, the former Expedia Group CEO, will become Seattle startup Convoy’s president and COO. (Convoy Photo)

Mark Okerstrom is shifting from travel and tourism to trucking, looking to apply his digital commerce expertise to a new marketplace.

The former Expedia Group CEO, who left the travel giant in an executive shakeup last year, is joining Convoy as the fast-growing Seattle startup’s new president and chief operating officer. Okerstrom will oversee Convoy’s finance, operations, marketing, supply and marketplace growth teams, working alongside  CEO and co-founder Dan Lewis.

The announcement comes as Convoy tops 1,000 employees, five years after it was founded by Lewis and CTO Grant Goodale. The company’s digital network is like ride-sharing for freight, matching shippers with truck drivers that have available space. Convoy is one of a handful of privately-held companies in the Seattle region valued at more than $1 billion, raising $400 million at a $2.7 billion valuation in September.

Convoy CEO Dan Lewis. (GeekWire Photo)

In an interview with GeekWire, Okerstrom said he first learned about Convoy early in the company’s history, when he was Expedia’s chief financial officer, sitting in the C-suite next to then-Expedia CEO Dara Khosrowshahi. Now the CEO of Uber, Khosrowshahi was an early Convoy investor.

That history is very relevant now: Uber competes with Convoy through its Uber Freight business, so much that Khosrowshahi divested his stake in Convoy after he joined Uber, to avoid a conflict of interest. Uber listed Convoy among its competitors, along with Amazon.

“I first started tracking Conroy shortly after it started, because Dara was an investor,” Okerstrom said. “He sat right beside me, and so we would always talk about investments, investment ideas. And so I was super intrigued about what they were doing.”

Convoy has raised $668 million over its lifetime from investors including Microsoft co-founder Bill Gates; Amazon founder Jeff Bezos; Salesforce CEO Marc Benioff; Code.org founders Hadi and Ali Partovi; former Starbucks president Howard Behar; U2’s Bono and The Edge; among others.

Expedia Group chairman Barry Diller, center, speaks with Dara Khosrowshahi and Mark Okerstrom during a 2016 event. (GeekWire File Photo / Todd Bishop)

Another Convoy investor is also familiar to Okerstrom: Barry Diller, the Expedia Group chairman, who cited a disagreement over strategy and disappointing financial results for the abrupt departures Okerstrom and CFO Alan Pickerill in December. That was before the pandemic threw the travel market into a tailspin.

After Okerstrom’s departure from Expedia, he was contemplating his next steps when Lewis contacted him.

“Dan just reached out at the right time; I had the background on the business. I hadn’t worked in an earlier stage company before. And yet there were so many interesting parallels between what we had done at Expedia and the opportunity ahead of Convoy. … I just said, ‘I just can’t pass this up. It’s gonna be a blast.’ ”

Okerstrom said he was also drawn by the environmental benefits of creating new efficiencies in shipping.

At some companies, hiring someone with experience as a public company CEO would foreshadow an initial public offering, but Lewis downplayed that notion.

“I don’t think that’s the primary driver here,” Lewis said in response to the IPO question. “If you were to listen in on our leadership team discussions, that’s not the thing that we’re spending our time thinking about right now. It’s how do we build the best business and continue to serve customers in new ways.”

They are spending time on expansion into new lines of business. Lewis pointed to Convoy’s recent launch of a payment service and fuel card for carriers as early examples of the types of programs and initiatives the company looking to roll out. The idea, Lewis said, is to “really think about trucking across multiple modes, but then also start to think about, how do we make the supply chain more efficient in all the places that overlap and interact with trucking.”

Lewis said the company has found in Okerstrom “somebody that can help us think about what that future looks like … across multiple businesses, really expanding to serve our customers.”

The pandemic has been a roller-coaster for Convoy, causing wild volatility in supply chains. The company says it saw demand for trucking surge in March and plunge in April, before rebounding to levels now approaching all-time highs.

The company cut a handful of positions early in the economic downturn, primarily in recruiting, after it reduced its number of open roles for the year. However, Convoy continues to add employees, and it is seeking to fill open roles.

For the record, Okerstrom hasn’t worked in trucking before, but he points out that his wife’s uncles are truck drivers in his native Canada, just in case that does anything to burnish his industry credentials.

If and when Convoy expands there, he said, “I’ll be a family celebrity.”

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