KAYAK’s New CEO on What No One Tells You About the Top Job

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0:36Hello, everyone, and welcome back to another episode of Sweet Success. I'm your host, Katie Klein, and today I'm thrilled to welcome Pierre Buehler to the show. Pierre is the CEO of Kayak, one of the world's most recognized travel search platforms, helping millions of travelers compare flights, hotels, rental cars, and more. Part of Booking Holdings, Pierre has been with the company since 2016 as chief financial officer and added chief operating officer to his remit in 2021. Pierre also served as CFO of OpenTable and prior to that, a senior member of Booking.com's finance team. He graduated from the University of Amsterdam with both a bachelor's and master's in financial economics.

1:18Pierre, thank you so much for joining us today. Yeah, thank you for having me, Katie. A lot of fun. I am really excited to talk to you today. This is a big moment in Kayak history. After 22 years as co-founder and CEO, Steve Hafner will become executive chair of Kayak and will take on a new leadership role at Booking Holdings, focusing on advancing AI innovation to support the company's long-term ambitions. So you are the first CEO to succeed him. And I'm curious, do you feel a greater responsibility to preserve what he created and what made Kayak successful in the first place? Or are you really looking at how do I define what the next era of kayak is going to be yeah katie that's my full-time job now is putting everything we do in either one of those two buckets there's an awful lot of good at kayak that's brought us to where we are uh that got us very successful over the last 22 years and we should absolutely continue that feed it nourish it and grow it there's some stuff we're doing that we should stop doing or do differently um and i feel really lucky seeing a little bit of both like this is not not taking over hope and I don't break it.

2:35There's definitely some stuff that isn't working well and we want to improve on it. There's also a lot going that we want to keep going. Can you give an example of something that you do want to do differently in the near term? Yeah, absolutely. The main thing that comes to mind is AI. It just got started. We dabbled in, we tried to figure it out. I think the first things we've done are very promising and look so powerful that we want to start feeding it into the main experience um and that's going to be a monumental change to the user experience on kayak which is um is much like anything else for years has been you fill in where you want to go and where you come from and when you want to fly and when you want to fly back um as you as we all know stuff's changing dramatically quite soon all our interactions with computers are going to be conversational, are going to be, you search the way you speak.

3:32And we want people to be able to do that on Kayak. That's probably the biggest change we're going through versus anything we've done in the last 10 years. So let's talk about Kayak's thoughts, opinions on AI and what you're doing. Because a lot of the conversation that we're hearing right now, and I think this is probably true when any technology is in its infancy, is like everything is going to change. It's all going away. The old guard is over. The new guard is here to stay. And if only we could just look back at history and see that it's never black or white like that, right? You guys have taken a really interesting hybrid model approach.

4:09Tell me what you're thinking about in terms of AI. Like you said, we are searching in a different way. So what is Kayak going to do with AI? Yeah, exactly. As you said, the hype was massive. the hype is always a little bit bigger than the reality but i don't think it's it's nothing i think ai is huge and it changes a lot of stuff it makes a lot of user experiences much better especially on the upper funnel where people are still digging for inspiration or maybe know they want to travel but don't quite have a a destination yet or a date yet um that type of use case upper funnel um pretty open-minded wasn't a perfect fit for the kayak product as it used to be we want kayak ai to allow people to do exactly that and bring them from uh an overwhelming amount of options and complexity to a place with more clarity more inspiration um and a better idea of what this trip's going to look like.

5:14That is very AI focused. That should be AI focused. If people get there and they're ready to take that step towards, I want to look at options, compare things side by side, make sense of rates and routes and baggage fees and all this complexity that sits in online travel. That is a classic moment for a more old school kayak user experience to step in and help people compare things side by side to get to the clarity and confidence that people need in order to make the actual transaction happen. I am a longtime fan of Kayak, a longtime user of Kayak. I actually lived very close to your Norwalk office for a year of my life.

5:55And what you just said about kind of making sense of all of the options and complexity, that is what attracted me to Kayak in the first place. And so it's really interesting to hear you talk about the evolution because it feel so obvious. And it also is so funny in a way to think about the way that it used to be so like, I'm going here, I'm doing these dates. You know, you had a little bit of flexibility if you wanted to be like, you know, surprise me with what time the flight would be. But it was very straightforward. And if I think about my own travel behavior, I'm a mom of two young kids. We knew that we had time off of work after Christmas, between Christmas and New Year's.

6:35We wanted to go someplace. But really, our parameters were we want it to be a direct flight. We want to fly from LaGuardia because I hate JFK Airport. We want to stay on the same time zone, ideally, maybe do a one-hour change. We want to go someplace warm. Other than that, we didn't really care where we went. And so talk to me about how kayak is going to support me in that kind of search journey going forward. yeah i think this is a place that everybody knows at any point in time everybody is a traveler right everybody is a traveler either you're on a trip or you're planning a trip or you're not quite planning a trip but you might have dreamt about a trip last night or spoken about a friend who was on a trip two days ago that got you somewhat curious to hey maybe i should make it out there once in my life as well for that the options used to be limited the first product i used on kayak well before working for for kayak um was explore which i i still think is such an awesome product to say hey i'm here i don't want to have stopovers i want to spend less than this tell me where can i go because dreaming about travel is travel is such an innate human experience right highly emotional um this deep desire to see things and explore things it's it's all quite deep kayak had that but nobody else had really organized travel inspiration um other than maybe i don't know lonely planet but even then you had to buy a book to to on a different destination if you knew where you wanted to go um right now with large language models all that stuff gets pulled in really quickly um and i think you're doing a really good job educating the world that i want to say hey i i want to go skiing i'll i'll tell a large language model um maybe kayak ai on kayak i want to go skiing i've got four days where should i go and it can become a conversation just like you used to have with that one friend that just went skiing that says hey if you're also into good food you can go here because the skiing is great the food's great that higher funnel inspirational stuff is is great it's it's straight away almost commoditized you can do any large language model you can do it on kayak ai and it's it's a really natural precursor to a phase in which you're decided and ready to say i know where i want to go i know when i want to travel now show me some options how much is that is that even something that fits in my budget, etc.

9:13Yeah. How can we as consumers, as travelers, trust or should we trust that the AI models are actually going to give us results that are best for us and not best for some companies, not necessarily kayaks, but some companies bottom line? I was just interviewing someone the other day and they were saying, look, travelers are more and more talking online, searching online with AI for where they want to go, how they want to stay, etc. Which link is, let's say, ChatGPT or Claude going to serve up? Is it going to be an OTA link or is it going to be a direct booking site link? So when you guys are thinking about how are you delivering to your customer, that's a lot of competing priorities, I imagine, from your perspective, because you're also at the end of the day a business and you need to be.

10:03Yeah, I think for Kayak, that purpose is really clear right we said people have an innate desire to travel people have an innate desire to compare options to create clarity in a in an atmosphere full of chaos um that's why kayak exists in order to help people that see an overwhelming amount of options to get it down to clearly these are the ones that fit the times i want to travel these fit my budget um and then to get options that that you've selected or the kayak i've selected on based on your filtering and your questions i think that's quite unique about meta search and what kayak does i don't disagree with you there's a lot of sites out there that have the same content but there's incentives everywhere to push you in certain directions and um yeah i i like meta search.

10:58And I really believe meta search serves an evergreen consumer need for neutral comparison. Absolutely. You're talking a lot about this innate desire to travel. And I think we saw that really come to the forefront after COVID of the boom that happened. And a lot of that has stayed like we as humans love to travel. I was speaking with someone the other day about the World Cup, and they said something about if you want to dislike America, read the headlines. If you want to love America, travel to America. And I don't think that's specific to America. I think that is a great example of the world and how we can learn about other people and see different cultures.

11:41I'm interested in hearing more about your backstory because in introduction, I mentioned that you went to the University of Amsterdam. I'm guessing you're probably from the Netherlands. So I want to hear about your origin story. Where are you from and how did you get to hold these really incredible roles, now the top role at Kayak? Yeah, I'm from the Netherlands. I've always traveled an awful lot. I, straight out of uni, I went into derivatives trading for a minute, which was a mistake. but I ended up with eBay really quickly that had just been founded a couple of years before which did form a bit of a love for chaos and growth and uncertainty I've always been an internet I worked for eBay for a long time I worked for booking for a long time it really grew a fondness for these fast-moving spaces I was a booking at the time I was maybe considering And next step, I got put in touch with Steve that you have already mentioned.

12:44And we connected quite clearly on this. How do you want to run a company in a space that is so vast that is still evolving where innovation is baked in because things are changing all the time? And how do you marry that with the amount of excitement I have for something like that? um we got going and and it's all been serendipity uh drenched all the way through and through as as many of these stories are at kayak i've loved working with these people i've loved working on this trouble this this these problems i've loved travel personally which gets me to feel like i'm doing something that matters but i also firsthand really understand our user like so many people that work at Kayak who know the experience of finding a new place or discovering a restaurant you've never been to or traveling to a place that is exciting, that feels exciting.

13:40I know the frustration of a broken experience, of lost luggage, of everything that comes with travel that's challenging. So I feel quite passionate about helping people have a better experience with their travel planning and maybe even while on trips. After sitting in the C-suite in different roles at Kayak, what looks different from the CEO chair than you thought it would when you were sitting in your other roles? The main difference for me is I've always thought of the CEO as maybe the least hardworking person in the company. You become like a tiebreaker. We have so many talented people all across Kayak that are much better at what they do than I would be at what they do.

14:24sometimes they disagree and they would come to the ceo and say hey can you help us out because we can't get on the same page the truth is very different like i'm at the table at so many of these discussions in the nitty-gritty and i'm loving it i'm surprised by it because i thought it would be different but i'm loving it and i think it's testament to kayak's culture maybe kayak size as well but we're incredibly transparent back and forth pulling people in and suddenly i'm actually having conversations about marketing, about product, about commercial in a way that I didn't have as a CFO because my agenda as a CFO would be so clear.

15:01And now I'm only on everybody's side, which is awesome. I'm actually enjoying that a lot more than I thought I would.

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16:11Why do you think that misperception exists? Or is it maybe true of some CEOs and just not others? I do think it's true for some other CEOs, which is probably where I got my perception as well. I've also personally always loved my own empowerment and the trust I felt in my work. I've tried to always make people proud, work hard, be proactive, try to do good things, not wait for somebody to point me in a certain direction. So I've definitely used my bosses in my life as, hey, I'll come to you when I'm in trouble. I don't go to you when I'm grinding it out and trying to make magic happen. I'm really thrilled with the relationships I have right now across kayak, where people seem to are okay with me being involved even when they're not in trouble.

17:03Yeah. Yeah. It actually probably strengthens the relationship because if you only come around when they're in trouble, that's a different vibe than one who is in the weeds with you and helping you to figure out the problems or leading to where you want to get to. Yeah, and I'd really believe it might be a little generational, but it gets the best out of people these days as well. I'm old enough that I worked for a hard-ass boss. I was going to be in trouble no matter what I did, which kind of worked for me 20 years ago. I don't think that gets the best out of people these days anymore. I love the people we work with, some of whom are 25 years younger than I am, but they're so good at what they do.

17:48Lifting each other up is really what gets a bunch of growth out of people. When you first started your career, whether it was that blip in derivatives trading or when you started with eBay and you were working for these harder bosses, did you always have this sense in your gut, like I'm going to be the CEO of a big company one day? Like, did you always feel that? Because I think a lot of people, particularly who listen and watch the show are extremely ambitious, extremely hardworking, and we are used to striving and climbing. But even for myself, seeing a top seat like the CEO, it almost feels unreachable.

18:26So did it always feel unreachable to you ever? Or how did you navigate that? Actually, I think I was ahead of the curve in terms of a little bit of care for true enjoyment, maybe even a sliver of work-life balance. eBay was founded by Pierre Omidar, who's an awesome guy, and just had these speeches that are really inspirational as well towards the human element in work and it's not all about grinding it out for for a quarter of a century and you might end up in a fancy place it's about showing up doing something you love then you're probably going to be really good at it and so i've actually never had this 10 or 20 year plan i i didn't i wasn't going by the seat of my pants either like i wanted to do my jobs really well i've i've gotten promotions early in life that i really enjoyed i felt the recognition it did egg me on to do a really good job the next thing i was handed i probably went like that job by job title by title for the first 10 years or so um when i joined booking maybe maybe that's a moment 15 years ago um that i started working closer with ceos and cfos and people with big jobs and and feeling like hey i'm an i'm an all-rounder like i'm i'm not a deep specialist i have opinions about anything and everything i like talking about anything and everything i could be suitable for this and i'm and i'm really good with chaos and stress which i i do think is something i've honed over being in this industry but that's another skill that i felt hey this might come in handy if i ever want to chase something like that um so no it's it's it's not happenstance.

20:16I did get my sights on this and started pushing a little bit in this direction a decade ago, but it wasn't on my mind when I was 20 something years old. And do you think part of that is the access? Like you said, starting to be in the rooms with other CEOs and realizing, hey, they're just people too. Oh, absolutely. But there's, yeah, there's, there's, that's a huge factor, right? And it's a thing in life where we blow up people we don't know but we've seen them i don't know stars and sports stars and everything um yeah they become a little larger in our life and the truth is nobody is larger in life like in their world quite similar which uh honestly is is one of the most powerful things about travel and you meet people in different cultures and you're going to figure out wherever you travel, you have more in common than you think you do.

21:13I love that. I couldn't agree more. You touched on work-life balance and particularly in the tech industry, that's something that doesn't always exist depending on the company. How do you think about that now in the CEO chair for you personally, as well as for your entire company and team? him yeah i heard a very long time ago somebody say it's not the hours you put in it's what you put in the hours and then and and this is well before anybody started talking about flow state and and all that type of stuff but it stuck with me because i believe it's so incredibly true i've gotten stuff done in four hours and i've gotten the same amount of stuff done in 20 minutes and the difference is how focused am I like am I ready do I feel good am I happy am I confident there's something there in the same I keep dating myself I remember reading getting stuff done the book um there's there's just so much of that that type of thinking that I got hooked on to I work with a with an with a zero inbox I have a couple of those kind of hard and fast rules why I try to be old school productive.

22:29If anything takes me less than two minutes, I'll do it straight away. A lot of stuff takes less than two minutes. I schedule, I work with my calendar. I've got my little spreadsheets. I'm somewhere still a finance guy. But I also feel that I know when I want to be productive in the creative sense. When we talk about company identity or about strategy or about next quarter or about a big presentation we're doing, i need to find the right moment to zoom in on it and then i know i can get it done in 30 minutes if i'm gonna do it because i plan to do it tonight at six like i know it might cost me four hours uh i got good at that um i had the risk of oversharing but i at some point i early on in life i decided i want to i know what kind of dad i want to be i want to be there had breakfast and a dinner um and i know that's not going to work out every day but if it doesn't work out four days in a row i start to feel really bad and i that's what i signed up for and it's not what i want to do i don't want anybody working a kayak to feel like they can't be the dad they want to be or the mom they want to be or or the partner they want to be um so i've got some of those types of rules that enforcing them and keeping them true for myself makes me feel really good about working hard.

23:54I'm flying to the U.S. on Sunday and I'm going to do five days there. They're going to be brutal days. That's fine because afterwards I'm going to do a holiday with my kids and I know I can spend real time with them. So that trade-off also allows you to double down when you need to double down. How old are your kids? 13 and 15. Yeah. And I don't think it's oversharing at all. I actually think one of the most powerful things for a very successful company is to have someone at the top modeling that because then you are subconsciously giving everybody else the permission and not making them have to choose or hide it or feel shameful about it.

24:39and at a certain point one thing is going to win and it's not going to be work it's going to be the family so actually what you're doing i think personally is giving people that opportunity to have that balance so that they can continue to build their career and things that they're passionate about professionally with kayak while not missing those important moments with their family yeah i'm convinced they can exist next to each other i think you can be the person you want to be outside of work and give 110 % at work. And I actually think giving 110 % at work is underrated. I think it's a lot of fun to go all in and give your all to a project or to really define success, chase it, and then achieve it in a project, in a job, in a title is more fun than people give it credit for it.

25:35So I'm all about work-life balance, which also means when work needs to happen, it's fun to go all out. And I'm trying to teach people that too, because I've seen too many people go like, well, I enjoy half-assing stuff because I'm so in love with my private life. I'm like, no, that's not a way to do it. You want to do it all. Also, you're not going to feel good as you're half-assing. Maybe you end up getting to then go enjoy your life, but you're not feel good, not giving your all to something. Cause that's just who are as most humans anyway. Yeah, I think so too. Is there a temptation you talked about, you know, knowing that if you work at a certain time or have the right focus, you can do something in 20 minutes that could potentially take you four hours at a different time or lack of focus moment.

26:22Is there a temptation then to do 10 X the amount of work in a day, as opposed to having that balance? A little bit, for sure. The work's never done. We have a great executive team that I'm thrilled with at Kayak. And we've got 800 people, really smart, travel-focused individuals that we love to empower, but the work's never done. I've never walked away from my computer because I was done. You grow a little bit of discipline saying, hey, I'm going to do something else now because i've been doing this for too long or hey i got done what i wanted to get done i'm gonna walk away even though i'm i have some hours left in me so yeah there's there's some discipline involved there i i like being productive i like pushing hard i i like pushing hard then more so than i thought the darwin effect should allow me to um but it feels good towards kayak towards all these people that work at Kayak to make sure we do everything we can in a space that's evolving so fast.

27:28So it feels like it matters what we do. Yeah, so I want to be productive. Having worked with many CEOs throughout my career, what I often see is your time is really not your own anymore. So much of it is scheduled, whether it be by meetings, interviews like we're doing right now, visits that you're doing, employee engagement, etc. And then at the same time, you talked about, you know, if something's going to take you less than two minutes, you want to do it immediately. You're focused on getting down to inbox zero. You really want to be in the brainstorming sessions and having that time and space to be able to ideate and come up with new ideas, which we can't unfortunately necessarily say this has to happen within this 20 minute block.

28:14I need to have my inspiration come then. So how do you think about that on a daily basis, whether it be how you run your calendar or your team runs your calendar, how you give yourself space for that? I think it ties back quite nicely to the hands-on comment I made earlier. We're all in the weeds. I'm not a distant figurehead in a tower that people need to request time with, which also means people know I'm working. I feel in our executive suite, we're incredibly respectful with each other's time and we're very in touch all the time. uh people ask me all the time like hey do you have 30 minutes or not like if not and um another thing that really matters is running kayak we've always done our own travel planning because that's right eat your own dog food we've that that's i love planning travel i love spending time on kayak looking at options i travel an awful lot for my job and i do all my travel myself which is weird because a classic executive assistant would always own your travel and your calendar.

29:21Because I own my own travel, I don't have an assistant. I'll do my own calendar as well. And I kind of enjoy it. I feel it really helps. Wait, you don't have an assistant? Nope. Wow. Yeah, it's funny. We're on Slack for instant messaging, which is what we love. I get thrown into slacks with a number of executive assistants because we're trying to do a meeting with a bunch of CEOs and then whenever somebody says what about this in this day and then every executive assistant responds and says um it works for Daniel um works for Glenn works for him and I always type works for Pierre but it just feels so stupid but uh no I take a little bit of pride in like nothing's beneath.

30:12Look at it. This is right. It matters. And it, it, it gives me some agency. Yes, absolutely. Because I think that is the difference from what I just said is what I have seen from others sometimes is when other people are in charge, you are not, you are just kind of puppeted around, not in a negative way, but this way, while I think, wow, that must take a lot of time. It sounds like you have such an efficiency to the way that works that it doesn't and it allows you to say you know i'm the dad who wants to be home for dinner yeah one one quick other thing that comes to mind is text 800 people but but i keep telling people it feels like 150 people like we're we're down to earth working hard trying to get stuff done we don't have too much of an ego like my media team is also not pushing me to be at two conferences every other week.

31:07I've all been like, whatever we think matters, or is helpful, or is really valuable, we'll do that. We're not going to send me around to sit on any next conference just because we got an invite. And I love the fact that we understand that internally really well. Yeah, well, that makes me feel even more special than spending an hour with you today. So thank you for that. Last thing I want to ask you about personally, you mentioned you have two kids, a 13-year-old and a 15-year-old, what do they think about what you do and the approach that Kayak is taking to travel? I'm curious just because their lens on travel must be so different from yours and mine's.

31:49We've talked about generations in this. And also what we talked about with getting in the room with other CEOs and humanizing it and making that feel accessible. I'm curious if seeing like, well, my dad's a CEO, does that make them aim higher in their aspirations as well? That's a really good question. My son, who's the younger one, talks about working for Kayak someday. And I wonder if in his mind, it's like a family business where one sort of succession plan, which there's not, obviously. Not yet. My daughter actually loves travel and travel planning and spends a lot of time on she spends her time on tiktok um but a lot of it's about travel inspiration the stuff the upper funnel stuff we started talking about which is insightful for me because i'm a bit of a dinosaur so that still is like oh yeah that's the way that works our brand marketing team understands this really well how to be um in those spaces where those audiences are um but it's it's been great and i try to tell them about it but i also try not to talk about work all the time, but they've been a really supporting crew.

33:01And yeah, I love that balance that I have there. And you travel so much for work. You mentioned coming to the U.S., but having some time with your family. But you also mentioned how powerful travel is and how much you love to travel. What are some trips that you have either coming up or places that you're like, when I have some free time, me and the family are going there? So I've been in the U.S. So I moved for the CFO job in 2015 to spend a year at headquarters and do it for a year there and then go back to the Netherlands. That year turned into seven years because I was just loving it in our Stanford office.

33:38After Norwalk, we moved to Stanford. We worked there every day for seven years, and it was awesome. Like being in person with people, still nothing beats that. We got really good at virtual, but I'm still traveling in order to be with people individually. So we're back in Europe. We have been back in Europe for a couple of years now, and we're still exploring Europe, re-exploring Europe. The kids are more American than they're European because they were young when we moved. Oh, they make fun of my accent all the time. Yeah. But now being back in Europe, do they or do they wish they had dad's accent?

34:14uh no they're still proud they're still proud they say my daughter says good job and stuff like that which we're rediscovering europe which has been awesome europe's got beautiful places most recently we went to the dolomites which is is such a and that that is scenery as dramatic as yosemite coupled with no crowds coupled with food as good as in the provence it has everything It's such an incredible region to visit. Yeah, yeah. Well, I want to talk a little bit more about Kayak before we close up. And really, one of the reasons that I think travelers fell in love with Kayak in the first place, it's my reason, is because you guys made comparing prices simple, transparent, and increasingly, that is harder and harder in our space.

35:08How do you ultimately help customers feel like they're making the best possible decision and they're not being taken advantage of? And also understanding what they're getting because every airline, every hotel has a different definition of what's included in the base fare. Yeah, spot on. And this is the story I tell internally all the time. Kayak serves a real customer need because people crave clarity, full stop, always, which is why everybody looks at their weather app 10 times a day. The craving clarity gets stronger if complexity increases. And that's exactly what's happening right now because of bundling, because of unbundling, because there's 15 types of economy classes, premium economy, economy plus, like none of it is comparable anymore.

36:01So when an airline tells you, you can fly in New York to Vegas for 120 and somebody else says well we will fly you 410 well that's not per se a better deal and we know it right one's with a bag and the other one isn't like that that is exactly the value that kayak brings the reason i think kayak's uniquely positioned or meta search is uniquely positioned to do this is because showing this transparently and really guiding people towards the clarity they need that gives them the confidence to make a book in is a real art. Comparison is a real art and it's not a conversational thing. Eventually it's a visual thing.

36:41It's probably a matrix type of visual that really allows people to compare how we've compared for centuries, which is side by side, show me these two things that people are trying to tell me are the same. What are the real differences? Can I select a seat? Can I not select a seat? Do I have to pay for this? Where I'm, where I'm actually flying. That's a real art. And I think Kayak's got almost a quarter of a century experience in optimizing the visual comparison. And I think that's still where the last mile really matters. And we're doubling down on it because it matters so much. And what you're talking about there, I think, is really about building consumer trust.

37:24And that's why I continue to use Kayak myself is because I believe that when I search on Kayak, I'm seeing everything. I'm seeing the best prices that are available. I'm seeing all the different places I could potentially book it. And then I get to make the decision for me, Katie, which might be a different decision for you, Pierre. It might be a different decision for the next person, right? So we talked about Kayak and the evolution with AI and where it's going. But how do you more broadly think about not only earning that consumer trust, but then maintaining it so that I continue to come back and believe that that is indeed the case.

38:04Yeah. I think what you're touching on is something very powerful, right? Katie wants to see something different than I want to see. In fact, when I travel personally or when I travel professionally, I'm the same person, but I want to see something very different, right? When I care about a pool, when I care about a gym, Like it's such a, it's miles apart. I'm the same person. It might be the same day. It might be an hour apart that I'm making these student groupings. What we're talking about is that hospitality in the general sense is personal, right? And I think that is exactly where Kayak and Kayak AI can play a massive role to make sure you tailor that overwhelming amount of options, overwhelming amount of complexity to the use case of that individual in that moment uh doing that effectively can be done with ai we'll definitely leverage ai if you tell us on kayak ai i'm traveling for work i got a conference in the empire state building i want to be nearby i need a gym in the hotel and i need to get an late checkout kayak can use that to filter that overwhelming results at down to hotels that fit that search.

39:18If it does that successfully, that's how you give people a bit of a delightful experience, which is what's needed. A great product is needed in order to gain that trust, to keep gaining that trust, and to give people a good reason to come back directly. Yeah. What are you most excited about when you think about the next five to 10 years for Kayak? I don't want to keep harping on AI, but it's going to change everything in the way we interact with computers. I'll quickly mention that corporate travel is another entire space of its own. It was ripe for disruption. Anybody who's used corporate travel tools 5, 10, 15 years ago knows that those experiences were a little stuck in the 90s.

40:06That space was ripe for disruption. Kayak gave it a go a couple of years ago, built a corporate travel tool with true leisure travel capability um at that grade it's it's so much better than anything else now it it was a big gamble and here we are we've got some massive clients on it it's working like a charm we got a team within kayak that is incredibly passionate about building corporate travel tools um and i think it's it's right about flipping into real prime time getting out there to anybody and everybody um and it could be massive because that corporate travel space has its own little cycle it's it's less priced focused it's more service focused it has differences but also similarities to leisure travel which we have so much experience in already um so i'm thrilled to see that come to fruition if in five years we're 10 times the size in corporate travel and we've managed to get to best in class where it comes to intersecting AI with leisure travel planning and comparison, I'm going to be quite proud.

41:16Yeah. It's so funny what you're talking about, too, because I feel like in more B2B spaces, like you said, corporate travel, so many companies make the mistake of treating it like B2B and not realizing that the end user is still a customer, still a consumer. So I'm what you're talking about, I'm thinking about, if I, you know, was working at a company that that was my travel booking software, I'd be like, this is great. This is so much easier versus other tools that I've used in the past, because at the end of the day, I'm still a consumer, even though maybe a more B2B product. Yeah, again, right?

41:55If you're making a B2B booking, you might be the same person making a B2C booking a minute later, have the actual b2b unique functionality um so travel policies and approval flows and a couple of things like that expense reports those were stuck in the 80s as well and we did a really impressive job bringing that all the way to the 21st century making it look spiffy and fast integrated within some messaging tools etc but the user experience is going to be wow because of the bdc experience and it based on that and being inspired by why why shouldn't be as good as booking for yourself. Right. Pierre, I want to ask you the last three questions that I ask every guest.

42:37And the first, what was the best hospitality experience you've ever had? So I mentioned Adolomites, which was really impressive. Probably the first time I really leveraged online travel planning tools, kayak and booking to make a trip through Patagonia was just something I'll never forget, but mainly because it's a long time ago. But it showed me, it was the first time it really showed me things have changed, right? This is not offline travel agents, which now do it online. Suddenly, it's real time. It's insightful. I have confirmations all in real time. It was the first time I really realized this industry is here to stay and will grow like nothing else because the experience is so much better.

43:25And what was the worst hospitality experience you've ever had? oh well so back in europe but it's everywhere i think over tourism is real and i think living in the u.s i've i've really come to love new york i love the the intensity of new york if you send somebody to time square they're not actually going to experience it that's not what i mean when i say the intensity of new york tokyo is awesome but if you go to shibuya square and you get buried in selfie sticks, that's not right. Sagrada Familia in Barcelona is beautiful, but the experience isn't all that good because it's one big pickpocket circus.

44:08I need nature personally to decompress a little bit. So I make it out to way more niche places in the middle of nowhere, like the Dolomites. And the experience is as good, if not better, than the beaten path. but then you get this true freedom to experience it without all the noise um so i i've been to all the overcrowded places that i just mentioned and i i think it's really important for people to realize if you want to see anything right if you want to go on safari the first results you're going to get sometimes don't quite give you that that open-minded free uncrowded experience that you didn't know you were craving for.

44:52Final question for you. What does hospitality mean to you? And is there anyone, it could be someone in your life, it could be a brand that you think has truly mastered it? One core belief, which I touched upon briefly, is that I think hospitality is individual, which is funny because everybody grows up being told someday you might get to stay at the Waldorf Astoria or don't you want to become a soul house member because that's that's what we're all chasing and the truth is we're no way we're all chasing the same thing like that's partly the beauty of of humans right we all have our little quirks and desires and um and I think if we really embrace that it it dissolves us all over these experiences it it fixes the crowdiness It allows people to appreciate what you really appreciate.

45:45It doesn't make you try to like something just because everybody else likes it. So I think that's really impressive. Players like Kayak do an incredible job appreciating that individual choice and telling, we had a marketing campaign. I don't know if it went anywhere, but the concept was go see for yourself or go make your own. The world's full of voices trying to tell you what to think, what to like, what to choose. It should be the opposite. Go see for yourself, right? Figure out who you are, what you want to be. Go find the option that fits that and then really enjoy it because you will. And I feel strongly about that.

46:28That is a perfect note to end on, Pierre. Thank you so much for being here today. Thank you so much, Katie. That was fun. All right, everyone. it's time for today's sweet summary where I break down the key insights and actionable takeaways from today's conversation. It's a fascinating moment for Pierre to step into the role of CEO at Kayak. He's succeeding a founder who led the company for 22 years while simultaneously navigating advances in technology that could fundamentally change the way consumers plan and book travel forever. Just another day at the office, right? It may sound overwhelming, and for most leaders, it might be.

47:10But Pierre's approach is actually pretty straightforward. Understand what Kayak is doing and has always done exceptionally well, nourish that, grow that, and at the same time, be unafraid to call out what isn't working and what needs to change. Pierre has something pretty powerful on his side, as he does both. History. After nearly a decade at Kayak, he understands the business, the product, and the people who built it and has the relationships and the trust to challenge the status quo without losing sight of what made the company successful in the first place. We talked a lot about AI today and Pierre clearly believes it will dramatically change travel planning.

47:56But Kayak isn't approaching that change by asking, how do we make everything AI? Instead, they're asking, where can AI be used to make the experience better? For inspiration, when you know you want to ski for four days or escape somewhere warm on a direct flight, but don't know exactly where you want to go, a conversation, for example, may be far more useful than a traditional search box. But once you've narrowed it down, you still need to understand whether that$110 flight is actually cheaper than the$120 one once you factor in baggage, seat selection, and everything else. And as Pierre put it, comparison is an art.

48:42Sometimes the best way to make a decision is still to put two options next to each other and clearly see the difference. He's not just adopting new technology for the sake of it. He's critically evaluating where AI can actually solve a problem better and where the existing experience still wins. It doesn't have to be an either or. That same thinking shows up in the way that he leads. Pierre assumed becoming CEO would mean becoming a tiebreaker. Someone people came to when they couldn't solve a problem themselves. Instead, he's found himself deeper in the work than ever before. talking product, marketing, and commercial strategy, managing his own calendar, booking his own travel, and sitting in the nitty-gritty conversations alongside his team.

49:31He's leading through participation rather than hierarchy, showing through his actions that absolutely nothing is beneath him while still empowering the people around him to do what they do best. Rejecting that either-or binary thinking extended to his thoughts on ambition and work-life balance too. In this area, I heard him reject another false choice, that you either go all in on your career or protect your life outside of it. Instead, Pierre knows the kind of dad he wants to be. He wants to be there for breakfast and for dinner. But he also talked about how much fun it can be to give 110 % to something, to define success, to chase it, to achieve it.

50:17Those things can coexist, but they require discipline. The work, as Pierce said, is never done. There will always be another email, another meeting, another idea, another problem to be solved. But unlike AI, our time and attention is finite. At some point, we have to decide that what we have accomplished that day is enough to close the computer and go actually experience the world that technology has made easier than ever to explore. And that concludes another episode of Sweet Success. If you enjoyed today's conversation, please subscribe, rate, and review the show. We all know how important those five-star reviews are.

50:59I also wanna say a massive thank you to each and every one of you for tuning in. It means the absolute world to me. And I'd love to hear from you. If you have ideas for future guests, new topics to cover, or even just want to say hi, don't be shy. Message me through our website, sweetsuccesspodcast.com or on social media at sweet success podcast. That's sweet like hotel suite. Once again, I'm your host, Katie Klein, and I'm super excited to see you all next week.