Cloudflare TV

🎂 Debby Soo & Alex Dyner Fireside Chat

Presented by Alex Dyner, Debby Soo
Originally aired on 

2020 marks Cloudflare’s 10th birthday. To celebrate this milestone, we are hosting a series of fireside chats with business and industry leaders all week long.

In this Cloudflare TV segment, Alex Dyner will host a fireside chat with Debby Soo, CEO of OpenTable and former Chief Commercial Officer of KAYAK.

Watch more Fireside Chats 🎂

Birthday Week
Fireside Chat

Transcript (Beta)

Hi, everyone. Welcome to our next Fireside Chat. I'm Alex Dyner. I lead the Special Projects team here at Cloudflare, and I'm incredibly excited to have with me Debby Soo, the CEO of OpenTable.

OpenTable, for those of you who don't know, is the leading provider of free real-time online reservations for diners and reservation and guest management solutions for restaurants.

Before OpenTable, Debby spent 10 years at the travel reservation company Kayak in various operating roles, including as chief commercial officer.

And prior to that, she was at Google. Hi, Debby.

Hello. Hi, everyone. Thanks for being here and spending some time with us. Of course, happy to be here.

This is great. So you've been in the Internet space pretty much your whole career, first at one of the world's largest companies in Google, and then more recently with industry-specific companies at Kayak and OpenTable.

So I'd love to start kind of with two super high-level questions about the technology industry in general and the Internet specifically.

What surprised you most about the past 10 years?

And then what are some of the predictions you have for the next 10 years?

I think what surprised me the most about the Internet in the last 10 years is I think 10 years ago, people, and myself included, were very optimistic about what the Internet can do.

It was almost like the power of the Internet and the positivity and efficiencies that it would bring to the world were really the growth and impact would be exponential.

It would change the way we access information and the speed in which we get information.

It's certainly done that. But 10 years later, we have a lot more cat videos.

It surprised me because companies like Facebook and Google have done so well that we have so much great human capital, the peak of engineering classes from schools like Stanford or Berkeley, MIT, focused on consumer apps like in the social media space.

So there's been a lot of energy on Instagram and Facebook and TikTok, and there's a lot of great talent going there.

I use those apps and they're really fun, but I wouldn't necessarily call them revolutionary changes.

Although, I guess you could say, but I'm not sure I would say they're revolutionary changes for positive change for humankind or mankind.

So I've been surprised that the tide has kind of turned in the last decade where big tech, I think 10 years ago, was seen quite positively and full of promise and potential.

And I think these days people are a lot more cynical or even jaded about what big technology and what the Internet has added to our daily lives and impacted our daily lives.

And then to your second question, oh, go ahead. Yeah. No, go ahead.

To your second question on what I foresee the Internet to be or technology to be in the next 10 years, as you mentioned, I've spent a long time in the travel space and most recently now in the hospitality and dining space.

And, you know, travel booking, for example, has gotten a lot more efficient in the last decade, but it's still pretty clunky, right?

Like we at Kayak, for example, we know for our logged in users, the trips you take, you know, the seat you like, what hotels you like.

Yet, you know, every time you come to our site, you're searching and selecting, in some cases, the same things over and over again, even though we know what your preferences are, right?

And so there's a lot more personalization that I think needs to be done and will likely happen, hopefully happen in the next 10 years, where something like going on a trip or booking, you know, a dinner reservation becomes so seamless and so easy that you don't really have to think about it or go actively do it.

It just kind of happens. We're recommending it to our users in a very easy way because we know a lot about you already.

So I'm not sure that the travel or hospitality space has fully leveraged the data that we have about our users to make the lives of our users easier.

And I think that's a trend that we will likely see happen in the next decade.

Yeah, it's interesting you bring that up.

A few days ago, we did a session with two folks in the fitness industry. So the founders of MyFitnessPal, and then Matt MyFitness, and they're making a similar point, which is what you want to do is actually sort of tell people, based on the data that they've given you, kind of what they should eat, when they should eat it, when they should exercise, for how long, and not just based on sort of general algorithms, but based on the fact that you know that when you suggested this meal, they actually ate it.

They didn't think, oh, my God, you're telling me to eat broccoli, but I hate broccoli, and I didn't eat it the last three times that you suggested.

And you brought up something similar when we caught up earlier today around also just having technology in restaurants, and you were surprised that it's not more tech-enabled inside the restaurant, that you still have waiters taking your orders and checking you in.

Yep. Yeah, I mean, think of going into a restaurant now, right?

A host usually seats you, right? So you have to flag down the waiter to order.

A menu has to be given to you, and then you have to flag down the waiter again to pay, right?

Where in some countries like China, all of that is already done through people's phones, right?

Apps like WeChat takes care of all of that.

You can order ahead. You can book exactly what table you want. You can pay for the meal on your phone.

You can add tip to that, right? So I think in the US, at least, we're quite behind on how a digital world gets into the brick and mortar world.

We're not quite there yet, but there's a lot of things that we do that with the technology we have, does it have to work that way, right?

And we've seen, like I said, in cases in China, where they use technology in a very different way than we do here.

Why do you think that is? Why do you think the pacing is different and the experiences are different?

I mean, I think in China, they have, like I mentioned, WeChat, they have these super apps where you go to one app for everything, keeping in touch with your family and friends, hailing down a car when you need to go somewhere, or buying a movie ticket, ordering a meal.

All of that is done in one place.

And so when China developed its tech and Internet ecosystem, these super apps really came into play and developed somewhat organically, probably in some instances with the help of the government.

And I think that that trend has just not really happened in the US and in much of like Western Europe, for example.

I'm not sure, I don't know if we will get there. I don't know if that's the model that that will take.

But that's how China has done it. And, you know, even at Kayak and OpenTable, we're part of a larger group, Booking Holdings, right?

So we have a lot of travel and hospitality brands within our group.

We talk about this notion of the connected trip, right?

Like, should we be connecting all of these brands,, Kayak, OpenTable, Priceline, into one app, right?

So when a user books their flight, they also book their hotel, they also book their meals, like perhaps they can even also, you know, get a car service.

Like, we talk about that connectedness a lot.

But getting it done is challenging. And we haven't really seen many companies in the US, you know, be successful at that yet.

That's interesting.

I mean, I'd also think that, you know, if you think about trends, you mentioned trends and the pandemic, and in some areas, the sort of accelerated, you know, existing trends in other areas, it's obviously been very harmful.

You've worked in two industries in restaurants and in travel that have clearly been significantly impacted by the pandemic.

I'm interested, I guess, two areas. One is in general, kind of what you're seeing there.

And two is, are you seeing kind of the adoption of, you know, things like OpenTable, Kayak, but perhaps the Internet more broadly in those two industries change because of what's happening?

Yeah, definitely.

We definitely have seen that. On the OpenTable side, on the dining side, reservations have never been more important.

So we've seen restaurants who have historically never considered or never needed to take, you know, online reservations, you know, now pivot and say they have to because of capacity constraints, right, that local governments are implementing, you know, within cities and for restaurants.

We are seeing restaurants be more open and move faster in terms of, you know, having a digital menu or contactless pay, right?

Some of those things I mentioned that China has been doing for a while, right?

You pay and order all through your app.

So I think the pace of adopting new technology is quickening with this pandemic, because restaurants have to pivot.

And we are literally going through an evolution of what dining out means, right?

Like restaurants also who've never considered a takeout or delivery business have now had to pivot into that segment to make sure that they stay afloat.

So you know, at OpenTable, we're doing everything we can to keep abreast of these changes and push the industry forward and use technology to help our restaurant partners who are really struggling right now.

I mean, even before COVID, restaurants operate on razor thin margins.

And now with the capacity constraints they're facing or the safety precautions that they have to be taking, it just makes running a restaurant even more difficult.

And I think technology definitely has a role to play here. And I think some of these trends are here to stay.

So even once the pandemic is over, right, I think restaurants will be like, wow, this is so much easier than having a paper and a pen and someone whose job it is to answer the phone for reservations, right?

So we're seeing that pivot and that adoption much faster, I think, during this pandemic than what we would normally see.

Interesting. I'd love to go back to the first point you made as well, when you kind of talked about the last 10 years and sort of some of the great things that tech has done, but also some of the, you know, resistance and perhaps the negative connotations, all the things you're talking about now around sort of the benefits of technology, and then also the data that you're talking about.

Do you think there is, how do you bridge that? How do you sort of balance perhaps the limitation that people's willingness to provide data versus the great benefit that technology companies can bring back to people if people are comfortable providing the data in the first place?

I mean, I think first and foremost, companies need to be really transparent on how they are using our users' data, right?

So you need to be asking permission and being very clear on what you're going to be using that data for.

So if it's, you know, for OpenTable, like, you know, do you want us to remember your dining preferences?

Do you, you know, give us permission to share your email address with restaurants that you've dined at before?

Like, we're very careful about making sure we have user consent for data that we are using.

I think the tricky part is not all companies operate that way, right?

I think for many of the big tech companies out there, user data is the currency in which the companies are run on, right?

Which adds to show how to target all of that.

And I'm not necessarily sure everyone realizes how their data is being used.

It's a timely question. I think I just watched the Social Dilemma on Netflix and, you know, I've been working in tech for a long time and I've worked at Google before, but even, you know, watching that, I walked away being like, oh my goodness, right?

Like, you know that these companies' business models are built on user data and being able to target, right?

And they're getting paid by companies to advertise to users.

But seeing it laid out that way was very impactful and quite frankly, scary.

And I think, you know, when I worked at Google, you know, over a decade ago, the company was much smaller then, but right, the mission of organizing and making accessible the world's information was a noble one.

You know, we felt really good about that. I was on one of the founding Google Maps teams called Ground Truth, where we were trying to map, digitally map a lot of the developing world, right?

There was an element of like, you felt really good about the products we were building and the good it was doing for the world.

And a lot of that work still continues, right? But I think there's this shadow side now that people are realizing that like, it's been awesome, but there are also some costs to that.

So it's just, we have to balance it. And I don't know if the answer is more regulation, you know, users demanding more transparency, upstarts in the space who, you know, come out and say like, you know, we're not going to use your data, use our services, but we're not going to cookie track and do all of that and be creepy.

So it'll be really interesting to see what happens in the next 10 years in regards to a lot of these business tech companies and the business models they have.

That's interesting. You've also, you have an interesting vantage point of having worked at kind of one of the, one of the Internet giants in Google.

And this is sometimes it feels like there are a smaller number of larger and larger companies in the industry.

And now at sort of industry specific companies that are, that are smaller than Google, I imagine you see as Google as a competitor as well and as a potential threat, you know, what's, what's the place of sort of large tech companies and more importantly, what's the place of the open tables and kayaks of the world you know, compared to the Googles and Amazons and Microsoft.

We've always viewed Google, you know, any, any competitor I think is, is good for whatever industry you're in and to have a competitor like Google is certainly forces us and pushes us to be better, faster, and more innovative.

And we just want the competition to make sure that we're all playing on a level playing field with the competition, right?

As for a place at the table for companies like kayak and open table, we believe really strongly that, you know, let's say an open tables case, we have 1200 people at open table who are laser focused on dining, our restaurant partners and our, you know, the diners who come to our consumer sites and apps, right?

So this is, this is our bread and butter.

Like we are all hands on deck focused specifically on this. Google is huge and has resources to throw a lot against the wall and see what sticks.

You know, on the travel side for kayak, Google's been playing in the travel meta search space for, for many, many years.

And it's not until really recent years where we've seen the impact of that in terms of market share and gaining traction with travelers.

So I think there are, there's always places for companies like kayak and open table who are very vertical focused and players like Google will always exist.

And it's, you know, my responsibility and my team's responsibility to make sure that we are keeping abreast of industry trends and we are moving fast and executing well, you know, and, and, and out innovating the, the big giants like Google.

It makes sense. Are there, you, you, you, you've recently joined open table.

I think it's, it's been a couple, a couple of, a couple of months now, so you're still relatively new, but are there things that you, that you see at open table and experiences you've had at kayak that are sort of immediately transferable and things that are similar as relates to the travel industry and the restaurant industry and the intersection of those industries of the Internet.

And I'd also love to hear what's different, what you kind of early on are seeing is a bit different in how you sort of approach the restaurant industry and how you leverage the Internet and how you might leverage the Internet going forward.

There, there are definitely parts that are very similar and parts that are very different.

I think, you know, kayak I grew up with the business. I think I was employee number 80.

It was before we went public or before we got acquired by booking holdings.

And so I know I learned kayak backwards and forwards, you know, through the, you know, the decade that I was there.

And so when I came over on the open table side as the CEO, it, the transition is different because my learning process is very different.

I'm coming in at a much different level than, you know, when I started at kayak as an intern, actually, when I was in business school.

But what I've realized is, you know, there's some core things that I think no matter what business you're in or what vertical you're in probably hold true, right?

Like making sure there's, you know, I'm working really hard on gaining focus and alignment at open table.

I think the company's been amazing and the amount of features and products has rolled out, especially during the last two quarters during COVID.

But what really makes the company strong is to make sure that each team is really bought in and aligned and we're all running in the same direction.


And that, that notion of alignment and focus and trust can apply pretty much to any company you go to, whether in tech or not.

There are certain, certainly themes, you know, or trends that go through both travel and dining.

I think that booking holdings, we're still very much trying to crack that nut to really open up the synergies between the travel side of the house and the dining side of the house.

So we're actively working on that. But, you know, it's, and how you run a company or a consumer facing tech company, I think it's not that different.

And I would imagine, you know, if I went to another tech company, you know, it'd be very similar.

Like we got to make sure we're all on the same page that we're all running in the same direction that we're working on the most impactful thing that we're using data to make decisions that we're taking care of our consumers and open tables case is a two-sided marketplace.

Also that we're taking care of our restaurant partners, right.

And then providing constant value to them. So it's, it's been very interesting and really fun to learn another business and the dining world and restaurants and all of that has, has been, it's just a really fun industry to, to be in.

And I can't wait until COVID's over so I can travel and go out and meet some of our restaurant partners and dine in their restaurants.

But it's been a fun time, a challenging time for sure, but, but really fun.

And it's surprised me how much I can leverage my experience at Kayak over on the open table side.

That's great. And I can't help ask as well, you know, in a very male dominated industry, the tech industry, you know, it's so great and so refreshing to see you as a you know, taking, taking the helm at such a great brand as open table as well.

Can you talk a little bit about that as well? Like what it, what it took to achieve the success that you've had your experiences as a woman in the tech industry and perhaps also advice to, to women who are earlier in their careers in the industry and look to you as a, as a role model.

It'd be super interesting to hear your perspectives on that as well.

Sure. I would say for people who are starting out women and men who are starting out in their careers.

When I look back on my own career, like, are there things that I can tease out like, or point to that, like, this is what really helped move me forward.

I think I've always had a really great attitude and I know that sounds hokey.

But I've always given, I've always given my best to whatever task I've been asked to do.

And some of that stuff is not glamorous.

I mean, even now I do a lot of work that is not glamorous, but especially starting off early in the world in my career.

I started my career off in finance, actually doing, I was doing M&A in the tech industry in Silicon Valley.

You know, and as an analyst, you're definitely not doing glamorous work.

And then when I, even when I went to Google, you know, I mentioned I was part of this project called Ground Truth, which was mapping, you know, the developing world at the time.

And we needed to get paper maps. Like we literally needed to get maps of, you know, third, fourth, fifth tier cities and countries in Africa or Latin America.

And like, we didn't have anyone to go do that.

So that was like, part of my job was to figure out a way to go source as many paper maps as we could in some of these towns or villages.

So then we could manually plot them into what you see as Google Maps or Google Earth today.

That was not glamorous. I'm like, I can't even read a map.

So just imagine for me, like, I was like, I can't, like, I went to college to do this.

This is insane. But I sourced a lot of goddamn maps for Google. And I did it really well.

And it was so rewarding, even though the work was grueling.

And so I think that like that can do attitude of like, yeah, I'm gonna get it done.

I'm gonna do it really, really well. I think got me really far. I think also, especially early on in your career, I remember like just really stressing out about like, well, do I take the Google job or the Disney job?

You know, like, should I work on maps?

Or should I work on Google shopping back in the day it was called?

You know, like, what business school do I go to? And like being really, like, really, really like agonizing over these decisions.

And what I've learned is like early on your career, any experience is additive, right?

There are really no wrong turns.

Any experience you have isn't a chance to learn something new.

So, you know, I think if you have that attitude, it makes it a lot easier to do not glamorous work, first of all.

But kind of just having that faith that like, you know what, like, as long as I keep putting my best foot forward, like I'm going to get to the place that I want to get to.

The other one of the last one I'll say is probably just speaking up and raising your hand and going for that opportunity or that promotion or trying to get yourself invited to that meeting that, you know, you might not necessarily be qualified to go to.

I've always been quite vocal and with my managers and mentors and what direction I wanted to head to and where I wanted to be by, you know, a certain time frame.

And so, you know, developing a thick skin because oftentimes the answer is no, right?

And not taking that personally and just, okay, I'll ask you next quarter.

And let me tell you the things that I've done, you know, from last quarter, this quarter, to show you why I think I deserve this chance to, you know, for this promotion or, you know, to go on this trip or to take over this partnership.

You know, I've always had that attitude.

I've always been very transparent, you know, with what I want and guiding my career in the direction that I think is right.

And I think for both men and women, but maybe especially for women, we tend to think like, oh, well, you know, I meet eight out 10 of those requirements.

So maybe I'm not going to raise my hand, you know, raise your hand and try because the worst thing you get is no.

And then you just try again. That's great advice. Yeah. It's true. You only sometimes say it's better to, it's better to take 10 swings and hit the ball five times and take them swing three times and hit the ball three times.

So exactly. Just keep swinging.

It's great. You know, so, you know, one of the things we'd like to do here is our 10 year anniversary week is also, you know, I talked a little about in the beginning is look forward.

And you mentioned some of your predictions. If you kind of step back on the industry overall, and you kind of think five years, you know, five years from now, whether it's, you know, question of gender diversity or ethnic diversity or geographically, we talked about China a little bit.

And when we were catching up earlier today, you mentioned that as well, how differently things look there from a technology perspective, and frankly, in different parts of the world.

You've talked about, you know, being more having technology more proactive and making recommendations.

What are some of the, what are some other big things that you think might happen?

Another interesting topic is the power of big tech companies.

Do you think that's going to be broken up? What are, what are some of the things you think will be surprised at five, five and 10 years from now, in the industry, in the industry overall?

I guess I'm going back to the question I started with, but it's always very interesting to hear from leaders like yourselves who have such an incredible perspective on, on the Internet and the industry overall.

I mean, I'm really hoping for self driving cars, as you know, like, when I think 510 years now, you know, like, flying cars, self driving cars, right?

10 years ago, we thought that that would be a possibility now. And I think even now, I'm still holding on to hope.

And we've seen some of that, right? And companies like what Tesla is doing, or what SpaceX is doing, I think is kind of the bright side of big tech, and how far we can push the envelope and make progress and make things more efficient and productive.

I think it's been really incredible to see a company like SpaceX do what they've done.

In terms of, you know, we're like even Amazon, right, that I'm, I'm out here in the backwoods of New Hampshire, and I can order anything I want and have access to anything I want is really, really incredible.

Or the fact that, you know, I have access to news, any type of news, anytime I want.

I remember, you know, when I was growing up, you know, like, we were an immigrant family, and my parents subscribed to a Chinese newspaper that would get delivered to our house.

So we weren't getting, you know, an English newspaper.

So when I was trying to like, for class, like read up on current events, like that was a challenge, like trying to go and get a San Francisco Chronicle or, you know, a New York Times.

And so a lot of technology and Internet has like, made information so accessible.

And I guess my hope is that we see more companies like SpaceX, the SpaceX's of the world, you know, moving things in the physical world with technology.

Well, we're out of time, Debbie, but thank you so much for, for being here with us.

Super interesting to get your perspective on the industry. But thanks so much.

Thanks so much. Thank you.