Aug 24, 2022

Convoy’s Dan Lewis shares tips for disrupting industries and building strong teams

Launched in 2015, Convoy leverages machine learning and automation to connect freight shippers with a network of more than 300,000 truckers across the U.S. The company is on track to generate $1 billion in revenue this year.

Speaking with Alexa Von Tobel on Inc.’s Founders Project podcast, Convoy founder and CEO Dan Lewis shares his approach to developing a deeper understanding of industries ripe for disruption and building the best team possible. Some key takeaways:

Examine the issue from all angles. When working out how to streamline freight shipping, Lewis spent time speaking with both freight shippers and truck drivers. He recorded his findings in lists titled “What Sucks About Being a Shipper” and “What Sucks About Being a Carrier.”

He also spent time learning trucker lingo to help him approach problems from their perspective. “I did not understand the culture of heavy, over-the-road trucking. I went on Youtube and watched truck drivers talk,” Lewis said.

Help your team understand the end user. Instead of taking his team to a resort for a leadership retreat, Lewis and company headed to a truck stop in North Bend, Washington, so everyone could go on ride-alongs. Each new employee is also required to go through full demos of the product experiences for shippers and trucking companies.

Make speed a feature. If you want to be the best, you have to break free of bureaucratic processes that emphasize “circling back” on a topic a week or even a month after first discussing it. Lewis leans into the idea of speed as a feature and encourages his team to come up with solutions overnight or the next day.

A lesson from Bezos. Amazon founder Jeff Bezos, also an early Convoy investor, once told Lewis: “You’re going to hit a point where to get to the next level, you’re going to have to spend a year and a half to two years just hiring. Lean into that when it happens.”

Lewis was taken aback at first — after all, speed is a feature! But now that Convoy has reached the next level, and Lewis has spent a significant amount of time hiring, he has a few important lessons learned. The first: Storytelling and messaging around the role are absolutely critical. People want to work on problems and be a part of a success story, not be handed a list of tasks to execute. “It’s a fundamentally more rewarding thing to do,” Lewis said. 

The second: Don’t over-level when hiring. “Don’t just give away big titles to people who aren’t qualified. Try to create respect and weight for the titles so they mean something in your market and don’t get you into trouble later by having too many people that are way too senior,” he said.

How to stay sane. “It’s really important to identify the things that matter to you and prioritize them. Write them down and do them,” Lewis said. He explains that founders are going to have to temporarily give up some things in life (fun trips, hobbies, keeping in touch with acquaintances) in order to build a company that succeeds. During Convoy’s early days, his non-negotiables were his immediate family, his extended family, and his company, and he compartmentalized his time so he could focus fully on each. 

Listen to the full podcast here ›

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