EP 19: A Conversation with Debby Soo, CEO of OpenTable

Thank you. I'm so happy to be here.

Well, thank you for giving us the opportunity. Thank you for being there and supporting the industry. We support a lot of organizations, but Ben's Friends is really near and dear to the organization's heart. Mickey came and did a session with our team. Lots of people dialed in. It was still maybe middle or end of the pandemic, so people were still remote. He told me later that a lot of our employees actually reached out because they were struggling. You would—I mean, obviously I didn't know who. The work is so important and we couldn't be happier to be supporting such a worthwhile cause. So thank you for letting us be a part of that story. We're very grateful.

Sure. I grew up in the Bay Area. I was born in Daly City, which is right south of San Francisco. My parents and family immigrated from Taiwan to the States. We did not have very much money. We lived in a two-bedroom maybe thousand-foot apartment. It was me, my parents, my grandparents, my uncle, and my aunt. We were real close. My aunt was busing tables at a Chinese restaurant. My parents were trying to find work. My dad was trying to learn English. I came up in that environment. My grandmother took care of me. We would go to Chinatown every afternoon to go grocery shopping. It was fun. I watched my parents really work. They ended up opening a brick-and-mortar travel agency that brought those big tour buses of Taiwanese people to the States. My dad was gone a lot in Taiwan. My mom was in the States running that side of the company and raising me. I'm the only child. It was lonely growing up because my parents were always working. My mom got sick a lot when I was a kid. She had her gallbladder taken out, her appendix, she had a brain aneurysm, she had her thyroid taken. She's in good health. She got it all out of the way. I think I mentioned that because being the caretaker growing up, and language was an issue—when you're in the hospital with your mom and you're translating, you learn really quickly how to navigate a system, how to be an advocate for a loved one, how to be the adult when you're the kid. That's been key to who I am as a person now and how I got to be where I am. There was always this pressure. My dad didn't go to college, and there was a big focus on education. They didn't know how to get me there, but they just knew I had to get there. I navigated and found my way to Stanford. I got incredibly lucky to get in. I went to Stanford and I didn't want to be a doctor. I wasn't smart enough to be an engineer, so business was kind of the default thing that people like me did. I went into investment banking out of college. After two years of that, it was comical. I wasn't a great analyst. Math is not my strong suit, so it definitely was not for me, but I learned a lot. Then I joined Google, which started the tech career. I was at Google for two years building out Google Maps. It dates me because when I worked there, MapQuest was the product everyone used. No one had heard of Google Maps. After Google, I went to business school at MIT. I was like, 'This seems very irresponsible because I'm taking on all this debt to go to school.' I stumbled upon a local startup called Kayak. I was employee number 90 as an intern. My job was to drive free downloads of our app. This was one of the first mobile apps. My second year at school, they made me a full-time employee. When I graduated, I stayed on. I was at Kayak for 10 years. We're sister companies, Kayak and OpenTable, both owned by Booking Holdings. That's how I landed my gig at OpenTable.

I did come in as the CEO. I started about five years ago, August of 2020, in the middle of the pandemic. There was a lot of noise and unhappiness when I joined the company. People were horrified that I didn't have restaurant experience. So many people who work at OpenTable come from the hospitality industry. I didn't have any of that. I was tech, I was travel. I had a reputation for being a hard ass. Probably true. There was a lot of resistance about my presence there. I get it. I had to learn it. I couldn't even go see it because restaurants were closed. I was working from my basement in New Hampshire. But it gave me a chance to learn about OpenTable. Even without restaurants, we were all closed. What do we stand for as a company? What have we been doing? How are we helping restaurants? Why are restaurants still churning when things are free because we waived our fees? It gave me space to meet on Zoom with everyone and really understand what's going on with the business. When things opened back up, I felt ready to identify the three or four things we had to do to get back in the game.

The first thing was pricing. We're expensive. We had this pricing model that was like no matter who you are, you pay a dollar per cover. That's been a dollar since 1998. There's no inflation. I realized quickly that not all restaurants are created the same. Restaurants are different just like people. Huge restaurants in Midtown need the demand from tourists and business lunch. They're happy to pay per cover. But the spot in SoHo that has 10 tables just needs software that works. They're hot and bursting at the seams. Why would we have one-size-fits-all pricing when none of our restaurants are of one type? I adjusted pricing. Some restaurants still pay a dollar per cover. Some choose to pay $4 per cover because they need demand during shoulder times. Some just pay the monthly software fee. We tailored pricing to each restaurant. Restaurants have to know the value they're getting from OpenTable. For a long time, there was a perception that there was no choice. The second piece was product. We were not innovating. We thought we defined the industry. But there were beloved product features that our competitors had that we did not have. We've spent the last five years going to town on product, making sure we have all the best-in-class features and more. The third piece is brand. Our website and app looked like they were made in 1998 because they were. We needed a brand refresh—how we show up in marketing channels, how we talk. We're not the star. Restaurants are the star. They're the content on our site. The flywheel starts with restaurants. If we don't have restaurants, we won't have diners. Diners aren't loyal to platforms; they're loyal to the restaurants. Our customer is restaurants. Our job is to showcase them. The fourth thing was culture.

The culture upon arrival was everyone was very nice. That's not bad, but when everyone is just very nice and decisions are consensus-driven, there would be many meetings with 50 or 60 people. Management by committee. It's not a democracy. Being nice and not giving real feedback, but then afterwards saying to your coworker, 'Man, that really sucked,' doesn't serve the company. We've tried to bring directness and transparency. I can't help it—this is how I talk. I don't have time for side comments. If it's bad, tell me because I'll say it's bad. We were slow, complacent, and arrogant. When I first joined, we were doing an advisory board meeting. I was showing the numbers for New York four years ago. They did not look good. We lost market share. One of my executives said, 'We can't show that to the board.' I asked why. They said it's not a good story to tell. But that's what's happening. There was resistance to owning that we lost our position. We have to see it, acknowledge it, live in it. How do we win? Now the culture—directness and candor are largely there. One of the best pieces of OpenTable's culture, even before, was this love for restaurants and hospitality. We still have that. We're moving faster, although still not as fast as I'd like. There's a lot of heart.

Me too. I love my job so much. You said something interesting about being nice. I was at our last leadership conference talking about empathy and compassion. Empathy without compassion is enabling. Everybody got real quiet. You see posters practicing radical empathy, but the analogy is: you see a hungry person on the street and say, 'That's terrible.' Compassion is getting them food. If you just have empathy, you're not engaged in the solution. When people come to work for us and we say we're a company that cares, it misleads them into thinking we won't have uncomfortable conversations or accountability—that's enabling. Danny Meyer always says, 'Before you say the thing, ask the question.' So before you hammer someone for being late, ask what's going on. Post-COVID, when we were short-staffed, leaders were afraid to have direct conversations. That creates a toxic culture with no accountability. Being nice is great, but being productive, holding accountable, teaching, having goals—that's where real self-worth comes from.

I thought the travel business was complex, then I joined the restaurant business—it's a whole new level. The sheer number of partners: OpenTable has over 60,000 restaurants. At Kayak, we had a couple hundred. I'm on the road meeting with restaurants all the time—both those on OpenTable and those not. Just the sheer number of partners is different. For the most part, we're helping mom and pop shops, not United Airlines or Expedia. This is a couple's livelihood. Their whole life is in this place. They're looking to survive, thrive, employ their team, take care of them. The stakes feel a lot higher here than in travel. You see the faces and know the impact if it doesn't go well. You feel the heartbreak when one shuts down. In both cases, you're using technology to enable a service, but I love restaurants because it's a human industry. It's messy and complex. But I love it.

Most restaurant owners don't have MBAs. It's incredibly human. That leads to my next question: technology is the conversation right now—AI and all that. I don't know where AI fits with restaurants. But on our end, people are going to crave human connection. I'm banking my whole life on that. How do you, as a technology leader, see AI playing a role at OpenTable?

I'm incredibly grateful and lucky that the hard work at OpenTable is starting to bear fruit. I'm not trending—OpenTable is trending. We've been working really hard. There have been grueling moments. Last summer I was in New York, and I met with a restaurant that spent 50 minutes ripping me a new one. They were mad about what happened six years ago. It's my job to listen. I apologized and went to another meeting with a prospect who ghosted me. I was tired. But the whole team experiences that. We're tenacious and keep knocking until the no becomes a yes. I'm excited that the work is moving the company in the right direction and helping restaurants.

Visiting restaurants. There's a special moment when the restaurant is closing, guests are gone, I'm lurking around. Chairs getting stacked, tables wiped, accounts reconciled. Then the team says goodbye. You know when it's a good team—hugs, kisses, thank you chefs. The first time I saw it was at Angie Mar's restaurant. She has a reputation of being a hard ass, but when the night ended, everyone hugged her. She knew about their lives. The connection after a night of service is beautiful. My husband was a rower in college. There's a thing called 'swing' when everyone is rowing perfectly in sync. I get to witness teams at restaurants do that when they say goodbye. That's the best part of my job.

Sometimes I feel discouraged because there are so many restaurants and we're a team of 1,200 people. I wish we could be going faster, sign more partnerships to support causes. I know what we need to do each year, but I wish the years were months instead of years. Some things can't be rushed. But I'm impatient by nature.

That's right. I'm not impatient, I have a high sense of urgency. Sometimes it's a lot to juggle—I'm a mother of young kids, a three- and six-year-old, a wife, a daughter. There's a lot to juggle. I'm not complaining; I live a blessed life. But sometimes I feel like I drop the ball.

Why is he writing like he's running out of time? I feel like I'm running out of time too.

Two surprises. One, I didn't expect to love the industry as much as I do. We're an infectious little bunch. I've been ambitious my whole life—milestone after milestone. At 31, I got divorced and all that went out. I'd always known I wanted to be a CEO. When I got the OpenTable role, it was a checkmark. But I didn't expect the work to be as meaningful to me. Usually, I get one thing and move to the next. Now I don't have a next thing. I feel fulfilled. My work feels meaningful. I'm not itching for the next thing. I'm happy and content but still pushing. The other surprise is motherhood. It's holy... Having kids is an experience no one knows until it happens.

No, I agree. They were in my belly. It feels like I have an appendage out there. They teach me patience. They force me to slow down. My six-year-old has selective mutism, a social anxiety where he cannot speak when nervous. For two years in preschool he didn't speak to a single adult. We did therapy and talking camps. Now he's fully verbal. I'm a control freak. I want to control the weather. But with kids, you can't control them. I can't force him to talk. I can only provide tools and build scaffolding. That lesson in motherhood is profound. It's like OpenTable: I can't force a restaurant to choose me. But I can do the work, be tenacious, and build the scaffolding so when the stars align, we're ready.

It means helping people feel like they belong. Seen, valued, and heard. When you make someone feel that way, it changes their life. I grew up not always feeling like I belonged. There were a lot of rooms I didn't belong in. The whole industry of hospitality, if done right, helps people feel like they belong.

Everybody. That's the best thing.

I hope that society continues to appreciate what the industry does. There's backlash on tipping. People should remember the role restaurants play in our daily lives. I want to say this carefully—uneducated people should stop commenting. The business model is fragile. DC passed a law about tip credits, and now restaurant closures are at an all-time high. You voted for something that's crippling us. Give us a chance to fix things. I hope the industry gives each other grace. Sometimes we mess up. That's okay. The industry can be unforgiving to its own. It doesn't need to be brutal.

I'm thankful for my health. Knock on wood. I'm thankful for my husband and my boys. They provide me with such a beautiful life. I'm thankful to be in a role where I feel I can make an impact. I'm thankful for restaurants. I have a deep love for them. I feel completely blessed. Sometimes I feel scared to say it, like the other shoe will drop. But there's so much to be thankful for.

Oh my goodness. This is amazing. Thank you so much.