Gregg, getting away from it all on Morgan Falls Reservoir, an offshoot of Georgia’s Chattahoochee River (Photo by Audra Melton)

Robin Gregg (MBA 2002) grew up in the West Virginia town of Martinsburg, 15 minutes from the midpoint of the Appalachian Trail. “Most of the people I looked up to were doctors, lawyers, or teachers, so it’s funny that I ended up in business,” she says. One of five students in her high school class to leave the state for college, Gregg majored in economics and East Asian studies at Washington and Lee University and worked as a consultant at Charles River Associates before coming to HBS. “I got to do such crazy stuff,” she says of her time as an MBA. “Warren Buffet came to speak. I wrote a case with Frances Frei, who is amazing. We had a 16-person roundtable with Meg Whitman (MBA 1979). There are so many experiences I remember vividly.”

After consumer-facing stints at Capital One and Revolution Money, Gregg shifted to B2B with a move to FleetCor, a provider of fuel cards and business-payment products, before becoming CEO in 2017 of RoadSync, a digital payment platform targeting drivers, warehouses, freight handlers, and merchants working in the $800 billion logistics industry. “The transportation industry is very transaction-intensive,” Gregg observes. “A driver might work for a different employer for each and every load—so there’s a lot of opportunity for friction.” The company’s products include RoadSync Checkout, which streamlines invoicing, payments, and operations for any of the multiple workers and vendors involved in getting goods from the loading dock to the warehouse.

Over the course of the pandemic, RoadSync grew from 25 employees to 100 and now operates with a hybrid workplace model. “My job is all about people—100 percent—whether it’s thinking about our culture or managing key customers and investor relationships,” Gregg says. “I jokingly told someone I’m the spiritual center of the company. You need to embrace that aspect of the job to get people excited about being here.”

Moment in time: “September 11 happened while I was at HBS. I’ll always remember being with my classmates for that. It felt like a bit of a protective bubble, which I was grateful for.”

Morning commute: “I lived in Davis Square, and every morning I would take the T to Harvard Square and walk across the bridge, rain or shine, to get to class. I always loved crossing the Charles and taking in the sights.”

Happy accident: “I’m a more quantitative person, and my management consulting experience—which focused on materials and metals—was very analytical, so I wanted a business profession that fit that. But I never specifically thought, Let’s do fintech.”

Front and center: “Now we all talk about the supply chain, which wasn’t the case a little over two years ago. It’s not lost on anyone that we don’t get anything without a well-functioning, efficient transportation system.”

New world order: “With a hybrid workforce, I’ve learned to overcommunicate our mission and vision. We have an all-hands meeting every Thursday, no matter what. Some people say, ‘Do we have to talk about the same thing every week?’ Yep. That’s the point.”

Customer ID: “The typical long-haul trucker is a mavericky, independent spirit who takes pride in what they do. Truckers don’t want to be told to download an app; but if they find something that speaks to and respects them, they can be enthusiastic in ways you don’t see in other industries.”

Podcast pick: “I love After Hours, with HBS professors. It triggers a little nostalgia for me. It’s delightfully nerdy, fun, and interesting.”

Bookshelf: “I read sci-fi and fantasy fiction with my 15-year-old son. We really enjoy anything by V. E. Schwab. There’s also a Scholomance series, by Naomi Novik, that we enjoyed—just imagine Hogwarts meets the Hunger Games.”

Local getaway: Kayaking and paddleboarding on the Chattahoochee River. “You can be 15 or 20 minutes outside Atlanta and feel like you’re in the middle of nowhere.”

Evening routine: “After work or dinner, I always walk the dog, a 70-pound rescue. She’s a super mutt, basically. And I try to avoid TV and screens for at least an hour before I go to bed. I have an Oura Ring and am maniacal about my sleep. Figuring that out has been the best thing for me.”

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