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Dan Lewis, former Convoy CEO and now a chief product officer at Microsoft, at the GeekWire Summit in 2019. (GeekWire Photo / Dan DeLong)
Dan Lewis, the former CEO of shuttered Seattle trucking startup Convoy, has joined Microsoft in a chief product officer role.
Lewis left Convoy last year after the one-time unicorn company went through a sudden shutdown. He joined Flexport in a technical advisor role after the logistics giant acquired Convoy’s technology.
Last summer Lewis started thinking about how AI will impact enterprise workflows. He had the chance to speak with Microsoft CEO Satya Nadella to talk about the tech giant’s vision for the future of work.
“I quickly realized that Microsoft is working on — more like running full speed towards — a very compelling vision that is equipping millions of companies and their employees, across the globe, with AI superpowers to do their best work and reach their full potential,” Lewis wrote in LinkedIn post.
His new title at Microsoft is chief product officer for Business & Industry solutions and Copilot AI.
The move marks Lewis’ return to Microsoft — though much has changed with the Redmond, Wash., company since he was a group product manager from 2008-2011 working on Windows and Outlook.
Following Microsoft, Lewis worked at Wavii, Google and Amazon.
Then in 2015 he became co-founder and CEO of Convoy, which built software to match truckers and shippers. The company raised money from the likes of Bill Gates and Jeff Bezos, reaching a $3.8 billion valuation before imploding in 2023.
The high-profile startup ran out of money as freight demand declined and rates for shipping decreased. At the same time, venture capitalists were paring back investments and it was difficult for later-stage startups to raise funds.
Lewis noted on LinkedIn that he’s from Seattle and has “always been a hometown fan of Microsoft.” He caught the tech bug in elementary school working with Microsoft DOS 3.0 on an IBM XT. His first job application to the company was rejected, Lewis said, but he concluded that it was a good thing in the end.
“[I]t caused me to dive in even more to learn everything about tech and building software so that it wouldn’t happen again,” he said on LinkedIn. “It is so cool to be back now at this pivotal moment in tech.”
