Dan Lewis’ career is hard to summarize in a sentence. He was a product manager at Microsoft, then an early employee at the Seattle AI startup Wavii, which Google later acquired. He made a stop at Amazon before ultimately boomeranging back to Microsoft, where he is today.
At this week’s Seattle AI Startup Summit, it was his experience building Convoy, the one-time unicorn trucking startup that shuttered in 2023, that he wanted to talk about.
But instead of relitigating what led to Convoy’s collapse, Lewis used his time on stage to share lessons to help entrepreneurs build a startup from the ground up.
Be deliberate about culture
Every company develops a culture, whether the founder shapes it or not, Lewis said. “The question is, are you involved in influencing what that is and helping to shape it around something you think aligns with your mission and the people you want in the company?”
Codify values only after you see what’s working
Back when Lewis was at Amazon, he asked then-CEO Jeff Bezos how the leadership principles were derived. Bezos told him that “he started writing stuff down when he first created the company, and then he realized he didn’t quite know what he was doing. So he waited a year to see what was working and what wasn’t, just to get a feel for how things were going.”
Anything that Bezos wanted to keep was codified. Lewis mirrored this approach for Convoy.
Make sure people know why, not just what
Founders shouldn’t have a culture in which workers accept decisions simply because the CEO says so. Lewis called that dynamic “demotivating,” arguing that employees who don’t understand the reasoning behind decisions can’t act independently or feel real ownership. Without that context, he said, people won’t feel like they’re truly part of the company.
Name teams after problems, not solutions
Lewis urged founders to name teams after the customer problems they’re solving, not the products they’re building. He pointed to his time at Amazon, where he built a Q&A tool called “Ask a Question, Get an Answer” for the ratings and reviews team.
The team pushed back: their mandate was to grow ratings and reviews, not launch someone else’s product. Had the team been named around a broader goal like customer or buyer confidence, Lewis said, its members would have been more open to creative approaches rather than feeling like they were “executing somebody else’s plan.”
Innovate deliberately
Invest time and energy into the areas that will really differentiate your company and “give you a chance to win.” Lewis acknowledged that it can feel uncomfortable to copy someone else’s innovations in undifferentiated areas, but sometimes it’s OK, especially when you’re not spending time on things “that don’t matter a lot.”
Storytelling is a startup superpower
Another critical cultural value is the company’s story. Have you crafted a narrative that is interesting, something people can relate to, and want to be a part of?
“Think about for what [you’re] doing, what’s the context in the world?” Lewis said. “What is the opportunity that’s just right there in front of us? What’s the tension point as to why we can’t get that opportunity? What is holding the world back from it, and how are we going to unlock it for everyone so it makes everything better?”
When it came to Convoy, for example, he had his work cut out for him early on trying to sign on new business.“Why would my customer, who’s never worked with a technology company, because they’re shipping freight, want to take a bet?” Lewis explained. “Because they want to be part of the story. It’s interesting.”
Clarify expectations bidirectionally
Trust between founders and employees doesn’t happen by accident. Lewis recommended sitting down — perhaps over a meal — and laying out expectations from both sides before the work begins. It’s a bidirectional process, meaning that both the leader and employee must be heard.
Hire deliberately — and reluctantly
When it comes to hiring, Lewis offered three tips.
First, every company wants team members who want to “show up every day, knock down walls, and make it happen.” But for more established organizations, they also need an additional type of employee, those capable of operating and innovating existing systems. This creates conflict inside a large business, Lewis said, because two cultures can’t live in harmony, nor is it possible to have “two compensation structures that manage the risk-reward.”
He argued that startups have the “pure play” advantage where there’s one culture, one risk-reward trade-off, and founders can focus on the type of person they need. In fact, Lewis thinks 80% of the workforce should possess that “wall-knocker” mentality.
Second, startups must be deliberate in hiring, applying filters to candidates throughout the candidate funnel, and rating how someone introduced themselves, spoke during the first meeting, and followed up. At the end of the process, companies will “only have people that really want to be there and want to be part of this.”
Founders shouldn’t invest a lot of time trying to convince someone to join their company. If they are, “you’re working too hard,” and that it’s “probably not the right sign for a startup.”
Lewis’ last tip: Don’t hire. He admitted that it may sound counterintuitive, but he wants founders to think that every time someone new is onboarded, “it was a failure to operate more efficiently and to innovate” in a way that wouldn’t have required bringing a new person aboard.
Instead, they should first ask whether there was an alternative way to complete the task — perhaps through AI — rather than increasing headcount.
And to be clear, Lewis isn’t advocating for the end of great hiring. Rather, he wants leaders to approach it this way: “Always consider it to be the thing that you wish you didn’t have to do. You wish you could have gotten it done without hiring that person.”
People don’t read instructions
At Convoy, Lewis said, they designed an operations system assuming people would carefully read each other’s notes during multi-day truck jobs with multiple support shifts. Most skipped the notes and started from scratch, irritating customers who had to repeat themselves.
When Lewis asked investor Henry Kravis of KKR for advice, the answer was blunt: “Stop building a system that assumes people are going to read.”
The lesson applies beyond operations. Whether it’s customers, employees, or end users, people scan for a button rather than read text. Founders should design processes and products, especially in the AI era, that work even if nobody reads the instructions.
Use data, and embrace concrete examples
One final piece of advice from Lewis: be data-driven. Leave the jargon behind and look to the data when something’s wrong, or there’s confusion, and you’re talking it through with your team or customer.
But also be specific — use clear, concrete examples, along with the exact words customers use, to clarify quickly.
Lewis closed his keynote with a note of humility. None of these lessons came easily, he acknowledged. In fact, many of them weren’t obvious to him until his experience at Convoy forced the issue. The company reached the heights of the startup world before closing its doors, but for entrepreneurs trying to build something that lasts, that hard-won experience may be exactly the point.
His talk kicked off a day of conversation at the second annual Seattle AI Startup Summit, a conference that brings together investors, founders, executives and others.
In addition to Lewis, attendees heard from AI2 Incubator’s Managing Director, Yifan Zhang, CopilotKit’s CEO, Atai Barkai, Edge Delta’s Founder and CEO, Ozan Unlu, MotherDuck Co-Founder and CEO, Jordan Tigani, and OSS4AI CEO, Yujian Tang, who heads up the conference.
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