Dan Lewis

Convoy's opening plan was to sign truck drivers up first, on the promise of loads that did not yet exist; almost none signed up, and Dan Lewis has said the company "completely bombed." Inverting the sequence, booking a shipper's real load before calling any driver, took app adoption from near zero to roughly 95 percent.¹

Lewis is the co-founder and former CEO of Convoy, a company that built a digital marketplace matching trucking companies with shippers who needed freight moved, in effect replacing the human freight broker with software. He ran Convoy from its 2015 founding until its 2023 shutdown, taking it from a two-person idea to a top-15 US freight broker before a freight-market downturn ended it.

Background

Lewis grew up in the Seattle area in a small-business family: his grandfather ran an office-supply distribution business that delivered around the Puget Sound region, giving him an early, hands-on view of how physical goods move through a supply chain. He studied cognitive science at Yale University as an undergraduate.¹ By his own account, most of his early jobs came through relationships and hustle rather than formal recruiting channels, a pattern that continued into how he built his founding team at Convoy.

Getting started

After Yale, Lewis spent about four years at the consulting firm Oliver Wyman, working on supply-chain and logistics engagements. He then moved through a run of Seattle-area technology jobs: a product role at Microsoft, where he worked on Hotmail and Windows and later helped build the Q&A feature on Amazon product pages; head of product at Wavii, a startup acquired by Google in 2013; and a director-level role at Amazon, where he built new businesses using the company's "six-pager" planning process. He credits Amazon's "single-threaded owner" model, in which one person owns a business problem end to end, as the culture that shaped the ownership mentality he later brought to Convoy. He has said he left Amazon after watching Prime's two-day delivery promise reshape consumer expectations of the supply chain, and concluding that trucking itself was still dominated by paper, phone calls, and fragmented human brokers.¹

Lewis co-founded Convoy in 2015 with Grant Goodale, starting out of a table at the University of Washington's TechStars office, with Maveron providing early office space. He recruited several founding engineers before the company was even incorporated, and delayed incorporating until an investor was ready to wire money, reasoning there was no need for a bank account before then. The founding bet depended on a recent technology shift: smartphones had only reached most truck drivers around 2014, which made an app-based dispatch model newly possible.¹

Convoy's first attempt at bootstrapping the marketplace failed outright. The plan was to sign up truck drivers first, on the promise of future loads, betting that a well-designed app and an appealing vision would be enough to win them over. Almost no drivers signed up, and Lewis has said the company "completely bombed" on this initial approach. The fix was to invert the sequence: instead of recruiting supply before demand existed, Convoy won a shipper first, secured a real load, and only then called an available driver with an actual job in hand. That change took driver conversion from close to zero to around 95 percent, because drivers were downloading the app to get paid for real work rather than to join a marketplace that did not yet function.

What he built

Convoy operated as a digital freight brokerage: shippers posted loads, and Convoy's software matched them to a fragmented base of trucking companies, most of which operated only a handful of trucks, using machine-learning-based matching rather than a human broker working the phones. To keep drivers engaged with the app through an entire job, Convoy paid carriers within 24 hours of delivery, against an industry norm of 30 to 60 days.¹ The near-instant payment gave drivers a reason to use the app for tracking and paperwork throughout a haul, and that usage fed Convoy the operational data it needed to improve its matching. As Convoy accumulated enough volume on individual routes, its algorithms could stitch two or three separate loads into a single batched, roughly triangular route, lowering a carrier's empty miles and letting Convoy offer a shipper a lower price while still improving the driver's economics.

The company grew quickly. Lewis has said Convoy roughly doubled its load volume every quarter for about eight consecutive quarters early on, and it expanded nationally in part after a cold approach from Unilever led to a pilot in Texas. Convoy went on to raise a total of about $668 million from investors, becoming a top-15 US truckload broker within roughly four and a half years of founding and working with Fortune 100 shippers. It reached a peak valuation of $3.8 billion in a Series E round in April 2022.²

The freight market then turned sharply. A prolonged freight rate recession combined with tighter capital markets undercut Convoy's economics and weakened the position of the strategic acquirers who might otherwise have bought the company. In October 2023, after roughly four months spent exhausting options to sell or refinance the business, Lewis notified employees that Convoy was ceasing operations immediately, with no severance and stock deemed worthless. About 500 employees were affected in the final wind-down.² Days later, Flexport acquired Convoy's technology stack and roughly 50 of its engineers for a sum Lewis and Flexport's leadership described as modest, and Lewis joined Flexport in an advisory capacity.² Flexport later sold the Convoy platform to DAT Freight & Analytics in 2025.

How he operates

Lewis has described speed itself as a defining feature of how Convoy operated in its early years, tolerating technical debt in the name of shipping fast; engineers marked deliberately hacky code with the comment "CTFU," for "catch the f up," meaning work that was fast now and would need revisiting later. He has said he personally interviewed nearly every employee up through roughly Convoy's first 150 hires, framing those conversations less as him evaluating candidates than as candidates evaluating whether they wanted to join him.¹ To judge whether an early hire could keep scaling with the company, he has said he asked whether that person could recruit someone as good as or better than themselves into the next role under them. Convoy's own account of how it fixed driver adoption has the answer worked out from a real failure in the field rather than from a plan drawn up in advance.

Where things stand

After Convoy's shutdown and its brief period advising Flexport, Lewis moved to Microsoft in February 2025, taking an executive role as chief product officer focused on business and industry applications of AI, including Copilot, after conversations with CEO Satya Nadella about the future of enterprise work. As of the mid-2020s Convoy no longer exists as an operating company; its technology and matching engine live on inside the Convoy platform now owned by DAT Freight & Analytics, and Flexport continues to use engineers and systems it acquired from the company.

Key facts

• Co-founded Convoy in 2015 with Grant Goodale, starting at the University of Washington's TechStars office.
• Convoy's initial driver-first strategy failed almost completely; switching to a demand-first model, booking a shipper before calling a driver, raised driver app-adoption from near zero to about 95 percent.
• Paid carriers within 24 hours of delivery, against an industry standard of 30 to 60 days, using the resulting app engagement to capture data that improved load-matching.
• Grew Convoy into a top-15 US freight broker within about four and a half years, on roughly $668 million raised, reaching a peak valuation of $3.8 billion in April 2022.
• Shut Convoy down in October 2023 amid a severe freight-rate downturn and tight capital markets; Flexport acquired its technology and about 50 engineers weeks later.
• Joined Microsoft in February 2025 as chief product officer for business and industry AI applications, including Copilot.