Debby Soo, CEO of OpenTable, 2026 Hospitality ICON awardee, in conversation with Dean Arun Upneja

Yes, I think that's probably a correct assessment. Humble beginnings. My parents are immigrants from Taiwan. They immigrated to the US. Actually, everyone on my mom's side, her siblings and her parents, they won some visa lottery. Someone had sponsored them and I was born in Daly City, which is slightly south of San Francisco. And for the first few years of life, it was all of us in probably, I don't know, a thousand square foot apartment. It was me, my parents, my grandparents, my uncle and my aunt. So yeah, I would say humble beginnings is fair. Even back then, I remember as a kid eating out was a really big treat, right? The household P&L couldn't necessarily afford doing that often. And of course, you know, we went to Chinese restaurants with sticky lazy Susans and very salty food. But it was just like a moment. I could feel it. Like I felt, you know, when we were there, armor was put down, right? Everyone was trying to learn English. Everyone was trying to figure out a way to make a living in this country. But at Five Happiness, which is on Geary in San Francisco, you know, they were speaking Chinese, they were eating food that they were used to. And so that experience that we did every week just stuck with me. And so, you know, today being a part of the hospitality industry and being a part of, you know, leading one of the companies that enables those types of moments that I experienced as a kid is truly special.

Sure. So I grew up in the Bay Area. My parents, after learning some English, they decided to start a brick-and-mortar travel agency. So they specialized in flights to Asia or bringing those big Asian tour groups in the 80s to America. And so it was great to watch them achieve their version of their American dream. Right? We moved out of the apartment into a condo in a suburb, then from a condo to a small house, then from a small house to a larger house. And so they really were able to, that social mobility for them was very inspiring to watch. My dad didn't go to college. He was orphaned at a very young age when he was in Taiwan. My mom's side, it's not like they had a lot of money either. But my dad in particular has a huge chip on his shoulder, right? Because he's been used to people looking down on him and just counting him out. And so I think in a lot of ways, I'm the only child. I am his ultimate trump card. So all the things, that big gaping hole on his shoulder that he wasn't able to do or he feels insecure about were things that I had to do. So education was important. So I remember, you know, starting in sixth grade, you start the SAT classes, the activities, what am I good at? English wasn't my first language. There's a lot of memorized words. I'm not great at math, especially for an Asian. And you know, that was a whole thing that we had to do. So I did end up going to Stanford for undergrad. Are you allowed to say that these days? Probably not.

I know there's press in the room. Kristen, don't record that piece. But you know, I went to Stanford and that was a really big achievement and I was very, very lucky. I'm not a good test taker. But you know, I did get in and then I went into investment banking because, you know, someone was saying if you're a smart person you go to McKinsey. If you wanted to go into business back in the day you went into banking or consulting. I chose banking because the consulting interviews were hard. And after that I went to Google and had this career. Now, I always say this when we talk about my resume, like it looks real shiny, but like behind every one of those bullet points, it's like a graveyard of rejections and failures and lots of tears. So it's not pretty. It's not meant to be pretty. It's supposed to be hard. And so I remember sitting in your seats as students. Where were the students? Like kind of back there-ish? Yeah. There, right? Like when the speakers would come, 'Oh my god, that seems so inaccessible.' I'm telling you, it's not. And it was hard and the door was slammed in my face a lot and luckily sometimes the door was open as well and you know, here I am. But don't buy the hype. It was a grind and it should be a grind.

My first job was at Citigroup as an investment banker as an analyst in tech M&A in Silicon Valley. I was not a great banker. You know, we talked about the math thing, like there's a lot of math in banking and I was in a class full of people who came out of the womb knowing they wanted to be in finance, like kids who went to Wharton. I studied East Asian Studies and a little bit of economics at Stanford. I didn't know what banking was. And so I remember my first review from my associate, 'She doesn't seem to know how decimal points work.' Like that's what we're talking about, okay, just to be very clear. But banking, as in all things, even as analytical as it was, it comes down to people. People do run, right? People pitch, you're talking to companies, you're talking to, and I am, dare I say, passionate and gifted about people, right? Like I love building relationships. I love understanding, okay, well, what makes this person tick? And how do I get into the club? Because the club wasn't necessarily made for people who look like me. For example, the managing directors every Friday had a poker game in the office and I don't know how to play poker. But I got a book and I learned because so many of the conversations of who got what deals and blah blah blah were happening at those games that I wasn't invited to. So I learned and then I got invited. So there was a lot of looking at systems that weren't necessarily set up for me and maneuvering within those systems to ultimately get my way.

Sure. So the one thing I will say about banking though is what it taught me. It taught me how to work hard and it taught me how to work hard professionally. Like I knew how to work hard as a student to your point. But when you're in the workforce it's different and all-nighters and long hours, like almost time was not a constraint when you're a banker. And so when you learn how to do that at a young age I think it's a really great way to kind of set you up for your trajectory later on. I joined Google after banking because I was like, yeah, peace, after my two years this is not for me. I learned a bunch and I joined Google and I thought I was joining Google's product search team, which back in the day it meant it was like their shopping experience. I was like, awesome. I like to shop. That's the internet. This is going to be a great fit. And I get there on day one. They're like, you're not going to be on product search. You're going to be on maps. It's like maps. I can barely read a map. I'm very spatially challenged. But here we are. So my job was to source various different means of maps, paper maps, transit maps. We were mapping the developing world, it was called Ground Truth. And at the same time I was doing BD deals with New York Times trying to get their restaurant reviews into Google Maps. I was doing deals with satellite companies trying to get aerial imagery, satellite imagery. Right now, like you Google Maps is a thing but just so you all know, MapQuest is even... anyone? Okay. Yeah. All right. Like that was the product that everyone used. And so at Google it was great. It was great to be at a company that didn't feel like it had any limits because the resources were just unfathomable, right? We're going to map the developing world. Debby, go figure out how to do that. The ability to think big at scale was something that I learned there. And then when I went to business school and I chose to go to business school because I wanted to get promoted at Google and they're like, oh you got promoted last year, like okay yeah. And well to the next level people usually have MBAs and I was like well I guess I got to go get one of those. So I applied to a bunch of schools and I ended up at MIT Sloan, which is kind of close to here. And while I was at Sloan as a first-year student, you know, in business school you go on all of these trips and I was paying for school taking loans and I was like this seems like very irresponsible to go to the British Virgin Islands while I'm borrowing hundreds of thousands of dollars. So I decided to find a job. And I stumbled upon a local startup called Kayak. They were back then in Concord, Mass, but now they are in Kendall, Cambridge. And I started there as an intern to drive free app downloads to our newly minted travel app because back in the day, who could even think that people would want to book flights on their phones? But here we are. And I ended up staying for 10 years. So, an intern in 2010 and then in August of 2020, I joined OpenTable as a CEO. And OpenTable and Kayak are sister companies, both owned by Booking Holdings.

You know, I wish it was like, you know, I'm fabulous and they just took a wand and anointed me CEO. No, it usually doesn't happen that way. Again, to the point of it looks shiny on the outside but it's not. I had wanted to be a CEO for a very long time. In college, that's what I wanted to do. I didn't know of what. I didn't know how. I remember when I was a teenager I saw Andrea Jung who was the former CEO of Avon. Do you guys even know Avon? Okay. The older people know. It's a beauty company where it's like a direct-to-consumer... Okay. Anyways, Andrea Jung, Asian woman. There weren't very many Asian women CEOs, you know, when I was growing up and I guess even today. And when I saw her photo on that magazine cover, I was like, you know, she went to Princeton, her parents wanted her to be a lawyer, then she ended up going to retail. I was just like, yeah, that's what I want to do. I didn't know how, but I knew that's what I wanted to do. So, when I was at Kayak and I was learning a lot of things. I was in product for a while. I was in marketing and I ultimately settled into my home on commercial because I like to drive the revenue and I didn't want to be a cost center. Because if you drive the revenue, it's harder to get fired. Okay, just side note, marketing is great, but nothing beats revenue generation. Yes, OpenTable. And we're going to get to some of the feedback from the restaurants in a second about our POS and all of that, but I'd wanted to be a CEO for a long time. OpenTable was within the group. It was one of the companies within our group. And so I'd had my eye on it for a long time, but it took me getting another offer at a totally different company. I didn't go look for it. They reached out to me to be fair, but I had to go get another offer and then I had to resign and say, you know, it's been a really great run. Thank you so much, but I want to be a CEO. I've been very transparent about the fact that I want to be a CEO and then the conversation was, I know, why would you go do that, like come. And so that's the actual story. And the story we tell publicly and Kristen's going to write about this because I know this is on the record is, you know, it was the pandemic and we needed dedicated leadership at Kayak and OpenTable. And that is the story that we tell and that is also true. But I just for the younger folks and the students in the room, it's not pretty. It's a battle. And you know, some of the people on this side from OpenTable know that when I joined OpenTable it was not a parade. People were not generally that happy, right? Yeah. You know, I didn't come from restaurants. I was known to have a bull in the china shop. I was aggressive. I have very high standards. I'm super direct. A lot of the things that you would think that are counter to what hospitality is all about.

And I felt that deep loyalty to Booking and to Kayak. Don't get me wrong, that was a very hard conversation for me to have because I feel like my career was made at Kayak. You know, my career was ordained by Steve Hafner and Paul English for those of you who know the Kayak co-founders. And also as a woman, it's not necessarily always the most, I don't know, well looked upon thing to be raising your hand constantly like, 'No, pick me, pick me, I want to.' And I've been doing that for a number of years. So you've been with... Yeah. And so for a long time, yeah, I was there for 10 years. So finally I was like, 'Okay, so maybe you're not going to pick me. So then I have to go pick something else, right?' And so, yeah, I'm only sharing the story because, again, it looks so pretty and the stories flow so well, but in reality, it very rarely happens that way.

Yeah. And like, you know, I started as a 20-year-old who didn't know how decimal points work. So, if I can do it, you all can do it. That's what we're talking about. It was grit, it was hard work, it was some luck, right? It was figuring out where are my skill sets? What am I good at? What takes me less energy to do than other people? And then figuring out how to mobilize from there.

So, back in the day, there were these things called phones, not mobile phones, like actual landline phones. And if you wanted to make a reservation at a restaurant, you had to figure out that restaurant's phone number, this was before, you know, right when the internet was starting. And then you had to call and usually leaving a message and then the host would call you back. And the origin story of OpenTable is in 1998, a man named Chuck Templeton, his wife's family was coming into town and he saw his wife spending an entire afternoon calling down her list of restaurants, you know, because her family was going to be in town and he thought, certainly there's a smarter way to do this with the internet and thus OpenTable was born. Online availability, getting that availability, which is the good stuff and we'll get to that in present day in a second, was hard to get, right? Because back in the day it was a piece of physical, Tarn remembers this because he's been with us for 20 years, but it was a piece of hardware like a wooden box that had a server and DSL, like I don't even know if the students know what DSL is. Right. But restaurants were basically transferring their book into this box, right? And then the machine would push that information from that clunky piece of hardware into the internet and thus online availability on OpenTable and on the restaurant's websites was born. But yeah, it was quite onerous back in the day before online reservations.

Yeah, shiny is probably not how I would describe the company that I found in August 2020. First of all, to be fair, it was in the middle of the pandemic. It was August, right? So, I don't know if a vaccine was out yet. Restaurants in a lot of cities were still largely closed. Those were harrowing times. But when I joined, you know, the folks who work at OpenTable know, like everywhere I looked it was like, oh why this, like there was a lot to tackle. But there were a few things that I had strong conviction about, which, you know, as a first-time CEO, I wasn't very confident and I didn't know the business. All those people who didn't want me to be CEO, it's true, I didn't grow up in hospitality, I didn't work in restaurants, I came from tech. And so even when I had strong gut intuition about this is what we need to do, sometimes I would question myself because I didn't have the data or the experience to back it. But there were a few things even with all of that I was like, 'Okay, there's some [__] up [__] going on here.' First of all was pricing. So during COVID, OpenTable, like many of our competitors, did the right thing and waived fees, right? That's the right thing to do. Restaurants were closed. We should not be charging. And so we waived fees which is great and that happened even before I joined. But then when I would look at the numbers, I'd be like, 'These restaurants aren't paying us, but why are they churning?' I was getting churn during free. So, you know, I go call up Tarn and folks on the account management team. They're like, 'Oh, it's because if they want to get the free, we're making them sign a three-year contract.' Remember that? Like, how [__] stupid is that? Okay, it's COVID. No one even knows if they're going to survive or be in business until next, like we don't know in weeks is this place going to exist. Meanwhile, like big bad OpenTable, 800-pound gorilla, is like sign your life away for three years and then we'll give you this next few months for free. So we got rid of that real quick, right? But we still lost some, like any goodwill we could have possibly garnered from doing that with free but sign-on was totally ruined. Pricing in general was an issue, right? We've heard about ARPU and yes, as a software company, ARPU is a metric that companies like us are evaluated against. Okay, I'm going to be very careful. Mary Kate, don't freak out. She's PR and this is, you know, we're publicly held by Booking, so I have to be surgical about how I say this. Every year since I've been here at OpenTable, six years I've been here, our revenue per restaurant has not grown. In fact, it has declined purposely. So, I'm watching Mary Kate's face. Purposely so. We can compete with flat-rate players that are out there. And for me, more importantly, I want every single dollar that our restaurant client pays us to be earned. I want restaurants to feel good about the check they're cutting OpenTable. There is value we drive, but was it at the $4,000? I'm making it up, so don't... real number. Like, was it at $4,000 a month? Probably not for two restaurants, let's say. So the revenue per restaurant in our POS has been purposefully and strategically brought down because we need to make sure we're matching price to value. Okay. The second piece though, is I have a boss and my boss has a boss. I always explain to my kids the hierarchy of like, he's like, 'But you're the CEO.' I was like, 'Let me tell you. No, no, no, no, no. I got a boss who's the CEO and then the boss has the board who has, you know, and then the board's boss are the investors.' He's like, 'Well mom, when are you going to become an investor?' I'm like, 'I don't know.' Okay. So I have a boss and as part of a public conglomerate or holding company there is a P&L that needs to be made and that P&L needs to increase and that profit needs to increase. That's just the reality of the world we live in and that's okay. I'm not complaining about it. I'm not woe is me. Just what it is, right? We're all in here trying to make a buck. So, every year that our POS has gone down, revenue has also gone up every single [__] year. That's true, right? How do we do it? Well, it was very scary. But we really relied on our sales team. We increased goal. So we made up part of the difference with our install base. So our install base had to grow more aggressively than the decrease in demonetization, right? So we made it hard. We increased goal by a lot. We hired more salespeople. That was one thing. Our product was not great when I started. Okay? You got all sorts of competitors in there and we were arrogant and complacent because we were the industry pioneer. I get it. When you've been number one and top dog for a long time, it's really hard to get back in there and roll up your sleeves and be like looking around and see what do we need to do. Sales people used to tell me that we were just like order takers. Like the orders would just come get faxed in, there was no boots on the ground. It just happened and you would make goal and that's not the environment we were in in 2020 nor is it now. So a lot had to change on the product. Like a lot. And we're a marketplace. We got restaurant clients and we got diners. And so because there's this flywheel of more restaurants equals more diners and diners more, you know, and it goes on and on. We had split the resources of the company equally between restaurant and diner. And this is to your point, let's be clear, restaurants are our customers. Restaurants, not diners, pay us. Diners don't pay us [__]. Okay? It is the restaurants that are paying us. So why would we spend equal amount of time on the diner side when this is the side that pays us? And more importantly, this is the side that generates and kicks off that flywheel because no one's loyal to a platform. They're loyal to the restaurants on the platform. We are not the star. The restaurants are the stars. Okay? We promote the restaurants. It's all about them. So, we need to make sure that our software is best-in-class, has all the bells and whistles, is not one-size-fits-all, just like we did that with pricing. And so, there was, this is very long-winded. I'm sorry. I'm going to stop soon. But there was a lot that we did, but pricing, changing our company mission of being restaurant-first and we're here to serve restaurants. And a lot of the culture, I've been here for six years. OpenTable's about 1,400 people. We've moved on and people have voluntarily left by the hundreds and that's okay because I know I'm different and I know it's hard but if we want to win there's no shortcut. It's just hard, right? We just heard we need less clicks, build me lovable, like all these things, right? They're right. We need to be doing those things, right? There are too many clicks. I mean, you should see some of the stupid [__] I used to see in our product on the restaurant side, like stuff buried 15 clicks in here when you're like just right. And we're still, we're 27 years old. There's technical debt we're still trying to get out of. But all of that feedback is fair and true because again, the clients are paying us, like we are the tech company. Make it work like magic. I get it.

That's absolutely correct. And you know, I've gotten this feedback as the CEO before like, my darn marketing team, my darn product team, they're like, 'We matter too.' And of course, that part is really important. But I think OpenTable, granted the app looks like it was made in 1998 because it was. But it is still a very intuitive and generally easy to use experience. I hope is what you guys think, right? Like to find the restaurant, to book the restaurant, the availability, all of those things. Because I think we have done a really great job. It is in dire need of a facelift I think, right? And we're working on that. And I had a lot of pushback from all over the company when I changed the mission at OpenTable to be 'we serve restaurants.' It's very simple, right? And then I did the whole Willard thing, there's nobility in service because there is, right? And we serve restaurants just the way that restaurants serve guests. But I do have 40% of the company being like, what about my job, like we work on the diner side. And so the mission is actually 'we serve restaurants so they can serve the world' and that piece is really important and we are actually spending more time on the diner side. Right, but again the order of operations is very important here. We had to start with the restaurant side because that's the genesis of who we are as a company. If restaurants suffer, we suffer. If they do well, we do well. We're not owned by a credit card company, you know. We're not owned by a food delivery company. We are intimately tied with how reservation-taking restaurants, how their P&Ls are. And so the point that was made earlier about, you know, don't, what was Eli's point, like your ARPU increase is my profit line degradation or something. He said it better than that but something like that. We are very aware of that, right? And the dollar per cover historically that we've charged since 1998, that's not adjusted for inflation, right? Every other cost has increased except ours. Right? And that dollar is not even a dollar in most cases, right? And sometimes, you know, if you want to go to flat, you can go to flat, too. We've been very flexible purposefully and there's more to do because you're right, in this day and age with AI we should be doing more with less. We should be able to do a lot more with the people that we have and that cost savings should be passed on to our restaurant clients.

You know, I would say in this day and age especially with AI, it's a fascinating time to be alive. So for the students in the room, like how [__] cool, right? Many of you I hope are AI native, right? It's just been part of your lives versus older people like me have really had to be conscious and purposeful about going and learning and experimenting with the tools. So the technology is going to get faster by the day, by the second. It's going to keep evolving and if we don't make sure that AI is building our product, help building our product and that AI is within our product, right, so reporting becomes easy but it's not just like some POSs out there have just an AI layer of questions and answers into reporting, I think that's great, there's so much more we could be doing and all of that is great and all that needs to be on and speed and first market is important. So all of that is true, but in a few years all of that will also be table stakes. Like if you're not doing it as a tech company, you're going to die, right? Let's be clear. But I think the one thing that being restaurant-first has taught me and just being at the helm of the company that I lead is that hospitality is all about heart. Like at the end of the day, what are we doing here, right? We're helping families celebrate. We're helping friends relax. We're helping moms who dine by themselves not have to talk to anyone else. Except like, yes, sparkling water, please. We're helping people feel taken care of. It's very human. And so yeah, all this technology and AI is, we need it and we need to adopt it and we need to build lovable in our products or the equivalent of all of that is true, but the crux of this industry is about heart and it's about people and it's about connection. And I think OpenTable, even the one that the company I found when I joined, had a lot of that and I think continues to have that. And I actually think our boots on the ground and our folks who are building relationships or fostering relationships with our restaurant partners, that feeling cannot be replicated by a robot. When Tarn goes into a restaurant and he's been with us for 20 years and he knows the restaurant's books inside and out equally well sometimes as the host and the GM, I've heard this said about you. You can't replicate that with a machine. You can't replicate shaking a hand and dining somewhere, looking someone in the eye with a machine. We can make their jobs more productive, right? The mundane computer back office stuff, yeah, all of that will go away, but the fundamental truth of having people and restaurateurs are very people people. They want to meet you. They want to make sure you dine there. There's a reason why direct online buying hasn't really worked in this industry, right? You hear it all the time. So I think that's the piece, the restaurant-first and the heart, that's what keeps me in this role, that's what I love about this role. And you've heard about what I love, I love people and I love figuring out what makes people tick and so how awesome is it that this gets to be my job, right? Because what you all do is literally all about people and connection.

Right. I told Stephen I was like, not for mom, okay. We're never going to get there but keep... co-board and then investor. So but what are you looking forward to? I feel tremendously blessed and I have a lot of gratitude for the life that I have worked very hard to achieve both professionally and personally. In 2010 or in 2011 when I graduated from Sloan, I was also, my husband wanted to divorce me. This is public. This is not like people know this. It was a long time ago. It's okay. But you know, we were at MIT and we were married and he was like, 'Yeah, I don't want to be with you anymore.' And so the reason I bring that up is I'm very intentional about not taking for granted my family, like my current husband. That makes it sound really bad. My life partner, the love of my life, the baby daddy of my kids. That takes work. He's also a CEO. We have strong personalities. I'm definitely the alpha. But it takes a lot of work. Like, don't believe the hype. We have to fight to make sure that our relationship and that foundation of our relationship is intact. I have two kids. I have a four-year-old and a seven-year-old, two boys. [__] being a mom is so hard. I think it's way harder than any working job I've ever had in my life. It's like having parts of your heart just out there crossing streets without looking. And when they suffer, all I want to do is take it away. And it's also one of the most rewarding things in my life. And then of course all the professional stuff, which we've been in. And so in 10 years, I hope that I've raised sons who are good and kind people who are well on their way of discovering what it is they love to do and what they're good at doing. And hopefully those two things intersect. I hope Dave and I still have a really strong relationship that we have now. And on the work front, I want to leave, I'm not leaving. Don't freak out. But I want to make sure whenever it is time, when I leave OpenTable and who knows when that will be, that I left it in a way better place than what I found it in. And I want to make sure that the changes that have been implemented during these last few years and going forward are lasting changes and that the company's better because I was there. That's really what I want my legacy to be. And I don't know, it could be another 10 years. I'll still be on the stage at 55 and being like, 'Yep, I've been the CEO of OpenTable for 16 years.' And I don't know what the next step is but I want to make sure the work that I do is meaningful and I feel like the work that I do at OpenTable is still very much deeply meaningful to me.

Oh, thank you so much. Thank you. Thank you.

What?

Thank you so much. Thank you.

Yes.

This is too many icon gifts, you guys. Thank you so much.

I love that.

Thank you. Thank you so much. Thank you. Thank you. Thank you.