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New Convoy CTO aims for Amazon-style innovation in transportation industry

New CTO aims to make data analytics user-friendly for truckers

Dorothy Li joins Convoy as chief technology officer. (Photo: Convoy)

After 23 years of leading the creation and adoption of Amazon’s (NASDAQ:AMZN) dominant services, Dorothy Li, who announced Thursday she is joining the digital freight network Convoy as chief technology officer, described the transition in terms of its potential real-world impact.

“I feel like I am going back to my roots,” she said in an interview with FreightWaves. “I started my journey at Amazon building out a lot of the backbones for its technology so it feels like I am coming full circle since Convoy is all about [technology] that touches people’s lives.”

During her time at Amazon, Li played a key role in changing the way that people consume content and how they expect supply chains to work, leading the creation of services including the Kindle, Amazon Prime and Amazon Web Services. 

This experience is why Dan Lewis, the founder and CEO of Convoy, had to have Li on his team.


“Dorothy has been part of inventing new things,” he explained. “They weren’t just iterations of an existing experience, they were groundbreaking. Consumers using those products have had an experience shift of the way they could actually purchase things and consume books. I think that’s a unique challenge when you’re inventing new things and changing the way that people have done something for a long time. I think a big part of Dorothy’s experience is thinking about these problems that are uncharted and figuring out how to get people who’ve been doing it the same way forever, to think about doing it differently.”

Li explained that over the past decade, her time leading AWS BI and Analytics has been geared toward democratizing data so that smaller companies have the same capabilities as larger enterprises. This experience is something she is hoping to offer to Convoy’s network as well.

“Particularly what I have been doing at AWS is really making data and analytics very accessible to nontechnical people by making it accessible through a user-friendly interface,” she said. “That taught me a lot about how to build a good user experience. I hope to bring that to Convoy by building out that same experience for carriers and shippers.”

Lewis is all in on that plan, pointing to the lack of user-friendly tools in the industry today.


“Everybody in freight has these ideas around analytics and insight but yet many don’t use it, it’s inaccessible or takes months for a data team to pull a query,” he said. “We are not only making it a good user experience, we’re building the back end and the data systems so the experience will be fast and easily accessible to everyone. That’s how you take somebody from an old world to a new world, by making the friction really low; you make it easy to adopt. All of this technology is something Dorothy has worked on at Amazon.”

While many companies are attacking the problems surrounding analytics in the transportation industry, what attracted Li to Convoy was the company’s ability to work backward from what the customer needs from these tools in order to build a great product.

“In the early days, Dan literally went to the docks in Seattle and observed what truckers did and figured out how to help them from what they were telling you [directly],” she said. “I think if your company value is rooted in working backwards and focused on the customer. … That’s how I think true inventions happen.”

After decades of leading innovative teams, Li expressed excitement at the prospect of entering an industry that is vital to the everyday lives of so many people.

“I came to the realization during the pandemic that essential things are available because of things that truckers do for us,” she explained. “I think about how the trucking industry touches people’s lives in a very real way. To me, there’s no better time than now to really get deeper into this industry, and I’m super excited to be learning more about it.”

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Grace Sharkey

Grace Sharkey is a professional in the logistics and transportation industry with experience in journalism, digital content creation and decision-making roles in the third-party logistics space. Prior to joining FreightWaves, Grace led a startup brokerage to more than $80 million in revenue, holding roles of increasing responsibility, including director of sales, vice president of business development and chief strategy officer. She is currently a staff writer, podcast producer and SiriusXM radio host for FreightWaves, a leading provider of news, data and analytics for the logistics industry. She holds a bachelor’s degree in international relations from Michigan State University. You can contact her at [email protected].