By now most people have discovered the joy of asking AI highly specific logistical questions. What's the best route to drive from Detroit to New York this weekend dodging thunderstorms and without losing cell service? Or, as Debby Soo, CEO of OpenTable, recently suggested of a typical ChatGPT restaurant search: "I'm looking for a seafood restaurant that's celiac-friendly, but has been nominated for a James Beard, in Boston, this Friday at seven."

OpenTable, now a Booking Holdings brand, launched in 1998. Its founder Chuck Templeton conceived of the idea after watching his wife make multiple calls to book one dinner. The pioneering startup in its earliest days had to install hardware at some restaurants to ensure a client could work with digital bookings.

Today, Soo needs to not only meet consumers and restaurants wherever they are -- and restaurant goers are using AI searches more and more, she said -- but also compete against a slew of rivals, like Yelp and Resy, in what has become a cutthroat space. That requires putting AI behind everything, of course -- while increasingly holding employees accountable for learning how to use it.

At OpenTable, the days of brown-bag lunches and AI experiments are gone, Soo said. Employees are expected to adopt agents assigned to them and hit role-specific AI usage goals. The CEO wants AI to help further scale the number of restaurants the platform serves (more than 70,000) without adding to its employee base of about 1,400 people. To that end, it not only has a team that builds AI tools, but every team has members tasked with looking for the chores a robot could do.

Onboarding a new restaurant's floor plans, for example, requires hours "with someone on our team, with the restaurant general manager, going back and forth on the phone," Soo explained. "And these days it should be as fast as taking a photo of the dining room, sending that over to us, and it just populates." (OpenTable launched this feature shortly after my call with Soo.)

Such ambitions might make employees nervous, but Soo, who became CEO in 2020, said she's in the camp who believes AI will liberate people from grunt work rather than replace them. The bigger danger to her isn't picking up AI fast enough. "I'm very transparent on the direction the company is going in relation to AI. I know people are scared, and I understand why they're scared, but I tell my teams all the time, 'This isn't just about your role at OpenTable,'" she said. "'This is about your own career, this is about investing in yourself, and if you think about ownership mentality...you are also the arbiter of your own career.'"

"Ownership mentality is paramount for me," she added, explaining that she traces that approach to a childhood watching her parents, immigrants from Taiwan, build a bricks-and-mortar travel agency. "The office was my bedroom when it started. So I've been watching how owners operate a business for much of my life." Now she lives that ethos, she said, and describes her leadership style as "tough but fair."

By the way, I asked a couple of bots about that hypothetical award-winning Boston restaurant with gluten-free options and a Friday opening. They came back with Mooncusser, Faccia a Faccia, and Row 34 -- sending me a link to OpenTable for one.

Lila MacLellan

Editor, CEO Brief

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