Convoy CEO Dan Lewis (left) speaks with GeekWire co-founder John Cook at a “Views and Brews” event Thursday evening in downtown Seattle. (GeekWire Photo / Kurt Schlosser)

For Dan Lewis, conviction and consistency are the driving forces behind his leadership style of trucking marketplace startup Convoy.

“Trust your instincts,” the CEO and co-founder said, speaking on the rooftop of Madison Centre building in downtown Seattle at GeekWire’s “Views and Brews” event.

Faced with a number of difficult decisions during the pandemic, Lewis said he sometimes made the mistake of relying on external insights to lead his thought process. This created concern within the company, he said.

He advised leaders to avoid second-guessing decisions, seeking external opinions, or relying solely on surveys. Doing so can erode confidence because leaders might not believe in what they’re saying, Lewis said.

On the other hand, Lewis said leaders can foster a sense of community and establish a shared ethos by prioritizing consistency. Maintaining uniformity, even in unfamiliar circumstances, often leads to better results, he added.

Founded in 2015 and backed by the likes of Bill Gates and Jeff Bezos, Convoy’s software automates transactions between trucking companies and shippers. The startup raised a $260 million investment round at a $3.8 billion valuation in 2022.

Lewis launched the company with his former Amazon colleague Grant Goodale. They started the company by hanging out at truck stops and getting kicked out of warehouses as they did market research when Convoy was just a kernel of an idea.

The Seattle-based company ranked No. 47 on this year’s CNBC Disruptor list. It is No. 5 on the GeekWire 200, our list of the top startups in the Pacific Northwest.

Convoy recently went through three rounds of layoffs amid economic uncertainty as it aims for profitability.

GeekWire co-founder John Cook interviewed Lewis at the “Views and Brews” happy hour event Thursday evening, hosted by tax consulting firm RSM. The conversation covered the Seattle startup ecosystem, the state of the trucking industry, artificial intelligence, autonomous vehicles, leadership, and more. Read on for our main takeaways.

Lewis finds leadership inspiration from sports coaches.

  • Convoy invited Seattle Mariners manager Scott Servais to study the startup and offer inspiration. Lewis said he’s inspired by the challenge sports coaches face in managing diverse personalities, attitudes and energy, while ensuring their entire team stays focused and functions every day throughout a season.
  • “I think it’s one of the hardest things you can possibly do,” Lewis said. “The leadership skills required to be an incredibly high-performing coach year-in-and-year-out is super hard and super applicable to running a company.”

Seattle’s startup ecosystem can continue to grow with the region’s tech talent.

  • Lewis, who was raised in Seattle, said the city’s tech workers are loyal to their company and have a genuine interest in problem solving, rather than being swept up in the hype. The tech community in Seattle has “more potential than ever,” Lewis said. “There’s an incredible talent pool here,” he said.

The reported truck driver shortage has many layers.

  • The government distribution of stimulus funding during the pandemic resulted in new buying behaviors, which increased demand for truck driving. As a consequence, a large number of new trucking companies emerged to capitalize on that demand, Lewis said.
  • However, the trucking market is currently in a recession. Lewis said it’s not due to demand declining, but because the overall supply of trucks “ballooned at a rate we had never contemplated.” He cited data showing a 28% increase in trucks and drivers in 2022 compared to 2018.
  • Lewis said the trucking market is reaching a “bottom” in terms of revenue drivers make per mile. He said many truckers are choosing to leave the market, rebalancing supply and demand.

Convoy has been using machine learning (ML) models for years, and the startup is looking into adding generative AI tools.

  • Convoy uses ML for trailer location prediction, pricing models, and route forecasting. “That’s like the old school AI,” Lewis said. The startup has not yet released generative AI features, but it’s working on new tools that automate conversations between truckers and other stakeholders.

While the hype surrounding fully autonomous trucking has waned, there are still practical use cases.

  • Lewis pointed to several factors as to why momentum in autonomous driving has slowed: politicians are reluctant to support anything that could cut jobs; autonomous driving tech is still limited in capabilities; and reducing empty miles, batching jobs together, and optimizing appointment times overshadow any “efficiency gains” from autonomous trucks.
  • In the long run, however, Lewis expects autonomous driving to play a “huge role” in trucking. He noted that before achieving full autonomy, there are intermediate levels, such as truckers staying in the vehicles and doing other tasks to boost efficiency.
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