The Business Strategy of the Biggest Player in Travel Tech with Rob Ransom, SVP at Booking Holdings

(Intro Narrator at 00:00:00) Today, we're talking to Rob Ransom, Senior Vice President at Booking Holdings, about the business strategy behind Booking.com, KAYAK, OpenTable, and more. You're listening to Joel Beasley, Modern CTO.

(Joel Beasley at 00:00:18) When the opportunity came up, I was pretty excited because I know Booking.com. But what I didn't know is Booking Holdings is way more than Booking. Can you tell me what it is?

(Rob Ransom at 00:00:29) Yeah, sure. So Booking Holdings is a holding company of largely online travel brands. It's a holding company. It's not a name that a lot of people know, but people do know our brands.

(Rob Ransom at 00:00:42) So Booking.com, you already mentioned. OpenTable, if you want to book a restaurant. Priceline.com, one of the oldest online travel brands in the industry. Agoda and KAYAK. So we have five major brands and cover a lot of different categories of travel and also the entire globe.

(Joel Beasley at 00:01:04) That is so cool. When you meet people in public, like kids' soccer games, stuff like that, most people don't know that, right?

(Rob Ransom at 00:01:10) No, they don't. But they do know the brands, right?

(Joel Beasley at 00:01:13) They do know the brands, yeah.

(Rob Ransom at 00:01:14) They've seen the TV ads or other things, or hopefully used the services. So that's how we'll bring it home. Holding companies don't get anyone excited, right?

(Joel Beasley at 00:01:25) Yeah, until the investors a little bit. Yeah, true, true.

(Rob Ransom at 00:01:28) Not at the soccer games.

(Joel Beasley at 00:01:29) Not at the soccer games, no. We actually used OpenTable last night. I do a once-a-month father-daughter date or father-son date where I have one-on-one time with my kids, and we booked it through OpenTable last night.

(Rob Ransom at 00:01:45) Awesome. Music to my ears.

(Joel Beasley at 00:01:46) Yeah, yeah, yeah. And so do you sit just over Booking.com, or do you sit at the holdings company and do strategy across the entire portfolio?

(Rob Ransom at 00:01:56) Yeah, I actually have a little bit of a dual role. For those that don't know our business, we have those five major brands, but Booking.com is far and away bigger than all of the others. It's the biggest one by far. And so several of us at the holding company also have a role with Booking.com. I started at Booking.com, and then that grew into a holding company role. So I look after strategy, corporate business development, M&A and investments, both for the overall holding company and also spend quite a bit of time with Booking.com. As I was telling you before, I'm actually based in Amsterdam. I've been there for quite a time, where Booking.com was founded.

(Joel Beasley at 00:02:37) Where did you start? You said you've been there for a while. When you first joined Booking, what was your role then?

(Rob Ransom at 00:02:44) Yeah, I joined Booking in 2014, so not quite 12 years ago. And it was to start some hotel technology services. We had just acquired two startups that I didn't have anything to do with, and they hired me to say, "Hey, we've just bought these two businesses. Can you help put them together, figure out a strategy, and let's put this together into a cohesive offering in the marketplace?" So we were offering things like websites and booking engines, some revenue and pricing tools to hotels. And that was the idea. So we did that as a sort of additional service to Booking's main business, which is the hotel marketplace.

(Joel Beasley at 00:03:31) And then did you rise up? I mean, you didn't do that for seven years. You did that for a couple years, right? And then how did you progress all the way to the holding company?

(Rob Ransom at 00:03:41) Yeah, a couple of things there. I think one is, over time, that role, I shifted away from the hotel technology piece. We did some reorganization. And Booking, at that point, was almost a 20-year-old company but didn't really have a strategy function, didn't have a business development function at the central level. So started to put that together for Booking.com. It was a period in our evolution. We're starting to think about what's the next wave of the business. What's the next strategy? We've been following a very clear strategy for most of those first two decades. And so we started to think as an organization, "Hey, what's next for us?" So I started to do that, created that team. And then when Glenn Fogel, who was running the holding company, also took on the role of CEO of Booking.com—so he has that double hat—he said, "Look, I need to have that strategy and business development function, but I don't want to have one at the holding company and one at our largest business unit. Let's just put it together." And so that's where it became similar functions on both sides of the fence, if you will, at Booking.com and at the holding company.

(Joel Beasley at 00:04:51) So then you just have this global strategy role now with the organization at large.

(Rob Ransom at 00:04:56) Yeah, that's right. And as I said, it's strategy, thinking about big strategic partnerships, so the commercial side. If we do get into investments or M&A activity, I get involved with that there. And then also, we have some smaller growth businesses that I look after too that maybe aren't part of one of those five major brands.

(Joel Beasley at 00:05:17) Other entities other than just the five major ones?

(Rob Ransom at 00:05:21) Yeah, they're smaller ones that we tend to think have high potential but maybe aren't big enough or aren't validated yet. So, you know, an example: we bought a business called FareHarbor many years ago. FareHarbor runs the software for tours and activities providers. So, for example, if you have a kayak rental service and you need some software to manage your reservations, maybe manage your inventory, availability of your boats, et cetera, FareHarbor is that kind of solution. So you would have that product, and then you go out there and make reservations and try and get people to come book your product. So that's a small business. We think it has high potential. It's a great business, a great category, but it's not nearly as big as the big brands we're talking about before.

(Joel Beasley at 00:06:11) They better have a pretty good integration with Booking.com.

(Rob Ransom at 00:06:14) We are doing that for sure.

(Joel Beasley at 00:06:17) Yeah, nice. What's the size? If you can share—I don't know if it's public or not—but if you could share, what's the general size of all the number of employees and technology?

(Rob Ransom at 00:06:27) Oh, gosh. I don't think we disclose the number of engineers or product and engineers, particularly, but, you know, call it in the several thousand. Yeah, yeah. And that's split across—each of those five brands have their own independent engineering organizations and product and design and all that. They're very focused and very product-centric businesses.

(Joel Beasley at 00:06:54) So you guys are a good holding company. You just kind of let them operate in their own world there so that you don't impact the culture and all of that.

(Rob Ransom at 00:07:04) Yeah, it's really been the philosophy for a long time. It's worked very well for us. We have these independent brands, and they all have—they built their own businesses. They built their own consumer audiences. But at the same time, they also have their own culture, their own engineering culture, their own product development. And so, where there is some coordination between the brands, the benefit of that is, one, these businesses, these engineering teams, these product teams find their own way, maybe solving a very similar problem or, generally, meeting consumer needs in travel. But different teams are going to find different ways to solve problems, which is great. You have some natural experimentation. And as you also know, different organizations will develop a different culture in terms of how they build product, how they think about it. Booking.com became quite well known for just a very, very rigorous A/B testing culture. And so did a lot early on in development, and have still to this day—we continue to invest in what we call the experimentation tool. And that's where we manage all of our A/B tests, all the test design, managing the traffic, looking at the outputs. So it's just a big part of how it shapes our culture. We'll take any idea, and we'll test it. And we'll see what happens out in the wild with real customers looking at what we're trying to understand.

(Joel Beasley at 00:08:29) You know, I don't hear that a lot. The last time I heard it was GoDaddy. They have a huge experimentation culture. They built their own internal experimentation tracking systems. And whenever I find that, there's always a link between high energy. I always feel like when I talk to those brands that are doing that, that they have in their culture a really good energy. And so that's a pro for people who might be looking for their next job.

(Rob Ransom at 00:08:58) Yeah, no, it's really great. And it also takes away sometimes—it can be politics about whose idea it is or if the senior person, you know, you have to do the ideas of senior management. And, you know, it's like, "Hey, we'll take all ideas and we'll test them, and let the best ideas win." And that's really been a core tenet of not only Booking but our other brands for literally decades. And it really shapes a lot of how we think about product development and thinking about investing and solving problems for customers.

(Joel Beasley at 00:09:25) Interesting. Now, does any of that bleed into—that's just for the product, right? It's not necessarily for how the teams work together?

(Rob Ransom at 00:09:36) Yeah, I mean, you mean in terms of how their teams are organized and things like that?

(Joel Beasley at 00:09:42) Yeah, like tools and different workflows. But when we're talking about the A/B testing system, we're talking mostly about features within the product set that you have.

(Rob Ransom at 00:09:50) That's right. Okay. I would say in terms of tools, you know, part of having a more distributed, decentralized culture is we have a long history of letting teams determine what tools are best for the job that they're focused on in a way that meets their needs, which is great. That gives a lot of independence to teams in terms of determining what they need. You can also imagine the flip side of that is you end up with—I think the other day, someone looked and said, "Hey, we have five or six different project management tools. We use Jira, but other teams have used a bunch of other stuff." And so you end up with some diversity there, which isn't always helpful. So it's a balance, right?

(Joel Beasley at 00:10:35) What are some of the travel trends? I'm not super deep in the travel space as far as, you know, being in the biz, but I do book flights. I do travel maybe two or three places a month. So what are some of the trends that are happening in travel?

(Rob Ransom at 00:10:50) Yeah, there's one that will be, I think, zero surprise, which is—because it's not just travel, it's the whole world—how is AI and generative AI changing how consumers, in particular, how travelers behave, right? And so that's far and away the biggest thing in the last couple years. I think it's obviously going to persist for the next few years, because it really hasn't—you know, probably the last big secular trend in travel that really changed things a lot was smartphones and mobile. And that's, you know, more than a decade ago when that shift came. And we were talking the other day about, you know, it sounds silly now, but I remember we were talking back in the early 2010s. There was a big debate: "Hey, should we invest in mobile? Do we need an app?" You know, these are questions that people really—that now maybe seem funny. But at the time, it was not nearly as clear that this was just going to be a massive shift in the way billions of people on the planet interact with not only travel services but all kinds of services. So in the AI world now, obviously, massive shifts. And in travel, you know, I guess I would say, where we're pretty convinced is that the new tools, whether it's the big AI platforms or just how it gets implemented in different services, are really a tool that enables people to think about their—you know, we talk about the travel inspiration, planning, the actual booking, and then managing your trip. It's going to change all of that, how people work with and manage their travel. Exactly how it's going to change, still very much that book is being written. And then I think the other thing that I spend a lot of time on is, from a strategy and business perspective, how is that consumer behavior going to change how the industry works, how the business models work, how different parts of the value—you know, different companies work together, et cetera. That's also still up in the air. But that's probably the—you know, there are other trends, but that's far and away the biggest one.

(Joel Beasley at 00:13:01) I could take a guess. Alright, so I don't know if this is a smartphone conversation in 2010. I don't know if this is three, five, or ten years out, but I'm pretty sure that in ten years, the way I will get my travel booked will be, "Hey, I need a flight from BNA to San Francisco Thursday, whatever, returning back Friday. I want direct flights. I don't want it to interrupt my sleep schedule. So you've got to find me some flights between, you know, like, 9 a.m. to 5 p.m., something in that range. And that's what I want." And then it comes back to me either text or voice. It says, "Hey, I've got one. This is it. This is the price. Would you like me to book it?" "Yep, book it. Which card do you want me to use or which account do you want me to use?" "Use the 7-whatever, whatever one." "Okay, done. Here's your confirmation," and it pops up on my calendar. That's what I think the future is going to be.

(Rob Ransom at 00:13:57) Yeah, I think that makes a lot of sense, and I would say it's probably not going to take ten years, right?

(Joel Beasley at 00:14:03) Well, there's two things. I think that's possible today technologically. I think by ten years, behaviorally, we'll be more comfortable with it. Because I noticed—tell me this, Rob. There's still some things for me that I could probably do on the app or my phone, but I feel like I need to go to a desktop to do it because not all the technologies are as high-definition and full-featured on the mobile versions as they are on the desktops. Do you ever feel like that with things?

(Rob Ransom at 00:14:38) Yeah, I think it's hard to say, but we still—we talk about it. More than half of our transactions at Booking.com are done on a mobile device, in the app, et cetera. So it's more than half the business. But that means that almost half the business is still largely done on a desktop, right? And what we find is, it's a little hard to say, but it tends to be either, like you said, more complex—you know, if someone's doing a more complex trip or they're trying to do more research and do a lot of comparison. There's certain things that just literally screen size and format may, you know, give people—or at least they're more used to doing it that way. So that's still relevant, right?

(Rob Ransom at 00:15:17) Very much so. I think it's interesting as you talk about a world where the scenario you just painted where a model is interpreting your preferences and your needs there and saying, "Okay, I hear what you're saying. And by the way, here's three or four choices. I've narrowed it down for you, and you can make a quick decision." That also may be less dependent on things like screen size and format. But there are still going to be big issues there in the way it's interacting, but it's also in trust. Trust is a huge part of travel, and we spend a lot of time thinking about that. Trust is a concrete thing, but travel for a lot of people, if you're booking a holiday, it can be expensive. It can be one of the more expensive things you do in a year. And so you want to have confidence that you're getting a good price, a great price. You want to have confidence that your money is being handled safely, securely, that it's not fraud. There's a lot of things that go into trust and the brand that's associated with that. AI doesn't really change that need.

(Rob Ransom at 00:16:28) And in fact, it may make some of those concerns bigger. If you're going to have that agent out there going and booking things for you, you want to know what they're doing. You want to have some confidence that they're doing what you say, they're not going off the rails, they're not getting scammed or booking something that doesn't really exist. All of those risks become even—

(Joel Beasley at 00:16:50) I want to install the booking.com in my ChatGPT. Are you guys showing up with MCP servers and things like that so that they can consume? If I'm an app developer, if I'm an LLM developer and I want to interface with your stuff, are you making that easier? I know you're probably providing an API just in general, but are you actually making it easier for the LLMs to consume?

(Rob Ransom at 00:17:14) Yeah, great question. So in October, I think it was, ChatGPT announced this app store where they had an event. We were one of the launch partners at booking.com, created an app. That's exactly that. We took our supply API, we put an MCP wrapper on that, and that's how the ChatGPT models are interacting with our supply when they're within the context of the app. So that's a—it's called an MVP. It's an MVP version of the app store. Our app itself is an MVP. But that's where we've started.

(Joel Beasley at 00:17:52) Can I perform a transaction, though?

(Rob Ransom at 00:17:55) So the way the app works today is you start the search. You have to invoke the brand on ChatGPT. So say, "Hey, booking.com, I want to go to New York City, and I need a hotel." You put your parameters in natural language. Booking will return five results based on that. But then when you pick one, it'll click out to booking, and you complete the transaction on the booking side, not on ChatGPT today.

(Joel Beasley at 00:18:23) Okay, so the discovery is there. If I ask it for a flight to New York from Nashville, it will pre-populate some link that I click—not hallucinated, an actual link—that'll take me to booking.com with that flight in my checkout or that flight just on the screen and then I add it to checkout?

(Rob Ransom at 00:18:45) One caveat. We haven't launched flights in there yet, so Booking does offer—but we started with accommodations. So yeah, I'm solving your hotel problem.

(Joel Beasley at 00:18:54) The hotel problem.

(Rob Ransom at 00:18:55) Yeah. We've got flights in the pipeline, and that'll come, but we started with accommodations. That's what we're best known for. So exactly that. You'd say, "Hey, I'm going to be in New York City. I need a hotel for three nights. I'd like it to be in Midtown or walking distance of the Empire State Building," or whatever is on your list. And then we'll return those results. But yeah, you actually complete the transaction over on the booking side.

(Joel Beasley at 00:19:20) Nice. And how's that going, by the way? I know that you're up at strategy, and this is a very detailed product feature. So if you don't have information, we can just move on from the topic. But do you have any information about how it's going? Are people using it?

(Rob Ransom at 00:19:35) Yeah, I think the headline there is it's just early days. It's early days on the ChatGPT side. I think they're figuring out the apps. Obviously, they're quite public with their huge and fast-growing user base. But the apps themselves, I don't think, are getting a ton of attention yet within their base. So what mostly we're doing is we're learning. We're seeing what people search for, and what we would call typical metrics of what's the volume of searches, how often are they clicking out, what happens if they click out, does that turn into an actual booking or transaction. So very early days. But that's why we're doing these things. It's not because it's going to drive business in the short term. We want to learn. We want to learn how natural language—are people searching for things in different ways, and how can we tailor the product to meet some of those needs? How are people thinking about this channel versus other ways that they find us? So a lot of things we can learn even though the overall volumes are still relatively modest.

(Joel Beasley at 00:20:44) Do you have to install the app on GPT, or you just mention booking and it knows?

(Rob Ransom at 00:20:50) No, you have to do a one-time—it's not, yeah, it's sort of an installation. You basically have to, they call it establish a connection or something like that.

(Joel Beasley at 00:20:57) Yeah.

(Rob Ransom at 00:20:58) So you do that once, and then when you search, you then have to say "booking." I think over time they'll—you won't need to invoke the brand names. They'll figure out a mechanism to say, you know, how do you bring it forward if you just say, "I'm going to New York," and you don't specify a brand. But right now, you have to specify that. And obviously, they launched this for things outside of travel too. So it's early days for the app store, but pretty interesting, I think.

(Joel Beasley at 00:21:25) It is. It reminds me of Google early days. Wow. That is so interesting. So you've got that partnership with OpenAI that you've done.

(Rob Ransom at 00:21:35) Yeah.

(Joel Beasley at 00:21:36) You've done anything with Perplexity, Microsoft, Alexa, any of those?

(Rob Ransom at 00:21:39) Yeah, we've talked to—we engage with everyone. Travel's always been a very interesting industry, which is there's a lot of, call it coopetition, to use an old term, which is there's people we compete with on one side of the business, and then we collaborate with them on others. So engaging with all those big platforms, whether they're building their own models, et cetera. We've done some work with Amazon and Alexa. Priceline was one of the launch partners there. Microsoft, where AWS has an AI store where we're putting some of our products there that are available. So really trying to understand what's out there and what's going to get traction in the marketplace. And it's just early, but it's fun to engage with everyone and see how fast the whole industry is moving. It's great to keep things going fast. It's amazing, I think.

(Joel Beasley at 00:22:33) Give me some insight to the non-technical peers that you have at the holding company. Are they fully onboard with AI? Do you find yourself having to convince—where do they sit, the non-technical people?

(Rob Ransom at 00:22:47) I think, I can speak for Booking Holdings—there's no real skepticism, I think. Really, because everyone's also in our own functions using the tools on a daily basis themselves to help, whether it's on the personal front or work-related queries and tasks. So I think the familiarity has just gone up quite a bit. Like any business question, it's like, "Hey, you know, these things—we have to invest money, we have to invest time. Are they working? How do we pick?" We've done a lot of—across our different brands—a lot of our engineering organizations are testing almost every different code generation tool. And, "Hey, what works? Why do we like one or the other? Which one's getting more adoption, more regular use from our engineering teams?" Again, back to we have different brands, so we've tested a lot of different ones and get different reactions. So natural question of, "Okay, that's great. Is it really helping? Is it just something that's nice to have? What kind of use cases, engineering cases are we actually leveraging the capabilities a lot more?" But even non-technical, they appreciate that. "That's great. Let's do that. Let's invest." A lot of willingness to invest, and we just see the potential to both reinvent how we engage with our customers, but also how we run the business and just a lot of opportunities to get more efficient and more productive.

(Joel Beasley at 00:24:15) You have a lot of technology background. Is there a CTO at the company or VP of—who is your most senior technical counterpart?

(Rob Ransom at 00:24:25) So we don't have a CTO at the holding company. Each of the brands has their own CTO.

(Joel Beasley at 00:24:32) And that's who you spend a lot of time with?

(Rob Ransom at 00:24:35) I spend time with them. Yeah. And also, you know, senior business leadership. But a lot of those—for example, talking about what code generation tools we're going to use and adopt, and are we going to let the teams kind of pick whatever they want? They use some use Cursor and some use Cody and all that? Or is it just, "Hey, we're going to adopt one and drive that?" That's really the CTOs of the brands are making those decisions, as an example.

(Joel Beasley at 00:24:59) Do they commingle regularly?

(Rob Ransom at 00:25:02) Yeah, they do. Yeah. They coordinate across the brands, and I don't usually join those calls. But I think definitely regularly, and I think they have some regular cadence on just talking about what's going on in the businesses.

(Joel Beasley at 00:25:18) Right. Just getting together quarterly or something just to see how things are going.

(Rob Ransom at 00:25:21) Yeah.

(Joel Beasley at 00:25:22) That's interesting too, because it's a whole different dynamic. A lot of people experience the dynamic of being the technical leader at a company. But being a part of this portfolio of companies, that's actually kind of interesting. It's a little bit different than normal.

(Rob Ransom at 00:25:36) Yeah. I think there's some natural experimentation, but also a great opportunity to learn. Some organizations are doing things differently. They've learned one way or the other, and we're very open among the companies. They just share everything. Say, "Hey, this is what we learned. This is what worked for us." But there's not a—you adopt that as you will, and teams kind of decide what they want to adopt and what they want to do on their own.

(Joel Beasley at 00:26:00) Well, do me a favor. When it gets to the point where I can have that conversation I described earlier, shoot me a text, be like, "Joel, it's there." And I want to try it out. I want to be in the future when it's technically there. I would be very happy to do an episode where I record booking a travel or something like that and do it on the air because I think that would be—I mean, that would be cool.

(Rob Ransom at 00:26:25) Fun. Yeah. It's the future.

(Rob Ransom at 00:26:27) It's—I've said, I was talking to a group the other month or so ago, and I said this is a really exciting time to be in travel and maybe in any industry because there's just so much stuff in play. New things, room for innovation, ways for people to rethink. You've got this disruptive technology, but we talk a lot about how it's just a tool at the end of the day. It's not—at least in our space, in our consumer space—it's not the product. It's a tool to help meet the needs of the customer. But that just unleashes all kinds of opportunities to figure out new ways to leverage this amazing tool in the service of our customers. So it just makes it a really exciting time to be in the business even though it can create some challenges, some risks, things like that. So I think it's fun.

(Joel Beasley at 00:27:15) You don't have to answer this next question. But is there anything real exciting that's coming up, that's about to come out soon that you're allowed to talk about? Because there's definitely stuff that's coming down the pipeline you are not allowed to talk about. Anything that is coming out soon that you're excited about that you can talk about?

(Rob Ransom at 00:27:35) Where my head goes is back to our culture of experimentation and stuff. We tend not to do big bang announcements and things like that. We tend to just do lots of incremental improvements that compound over time, and so that's less exciting. It doesn't lend itself to a lot of press releases, et cetera. But that's really much more the philosophy of how we approach these things.

(Joel Beasley at 00:28:00) That aligns with my philosophy. I'm a huge fan of small improvements over time add up. It's how you can leverage time itself in order to get a better result. A lot of intensity in a short period of time, that was not working for me. My twenties were so tough, Rob, because that's the mindset I had. And then I started listening to Tony Robbins, different self-help and different thought leaders, and I realized that the individuals that seem to have the most consistent level of success where it's not magic, it's more of a consistent thing that they were doing as a system was the small habits over time compounding. And so I said, "Okay, let me try that." It's been about, I don't know, twelve, fifteen years since I've started that and my life is just infinitely better.

(Rob Ransom at 00:28:50) Yeah. That's great. That's very cool to hear because I think you're right. It applies certainly at the individual level, but if you apply it to an organization too and a corporation. I think if I had to put a point on Booking Holdings' philosophy, we're much more like that. We're much more "do it first, talk about it later," as opposed to some organizations that are the opposite. They'll lead with the press release, and that's just not our style. And, you know, that can work for some companies, but just not really how we go about things.

(Joel Beasley at 00:29:20) Yeah. I have a done list, so I write stuff on the list when it's done. I'm going to go do something and I'm going to write it. That's just a little bit that I like doing.

(Rob Ransom at 00:29:28) Yeah.

(Joel Beasley at 00:29:28) Because I noticed when I was making lists, I started with to-do lists. I just got in this list mode where I'd make this list and I'd be exhausted after making the list. I'm like, "Ugh, I just did that list. There's so much stuff to do." But then I realized if I just have energy and I just go do things and I get to write it down, for whatever reason, for me, that worked.

# The Business Strategy of the Biggest Player in Travel Tech with Rob Ransom, SVP at Booking Holdings

(Rob Ransom at 00:29:47) That's funny. I read a funny story once. I don't know if this applies to you. It showed that you're really a list person if you sometimes will write things on the list that you've already done just so that you can cross them off. I don't know if you do that, but that was a sign of you're really committed to the list at that point if you've already done it, but you just get that dopamine hit from crossing something off or checking the box or whatever.

(Rob Ransom at 00:30:09) So—

(Joel Beasley at 00:30:10) You've got it. You've got it. Yeah, by the time I get to making the list. Yeah. You've been in tech and you've been in a leadership position for 30 years now. And I did, you know, stalk you a little bit online, so I saw that you started at McKinsey and you worked your way through marketing, product, and strategy, and all these cool things. As you've gone through this progression, you've picked up a lot of useful things along the way. And one of my favorite questions to ask guests is for a piece of leadership advice, but there's constraints. And the constraints are it's something that you learned early on, like someone told you or showed you. You tried it and you were like, "Oh, this works," and it stuck with you for a long time. I want that piece of advice.

(Rob Ransom at 00:31:02) That's a good question. I think—I don't know if this fits your model, your template, Joel, but I would say it's almost anti-advice, which I learned over time by starting to do it wrong, or at least what I now believe to be the wrong way, and getting to the opposite. And I think, I'll just focus on strategy and business, which is I think early on in my career and definitely when I was at a big consulting firm, McKinsey, there's a belief that strategy is really complicated, and the more complicated it is, the better. It must show how smart you are to figure out something that's so complicated, and you go down that. And over time, and I really believe this strongly today, the most powerful strategies—and the most difficult part about it—is finding the simplicity and the elegance and the focus and really being able to stay focused on something that is clear and simple and understood by your organization for an extended period of time. Right? And maybe that sounds obvious. It certainly wasn't obvious to me for a lot of years, and I've just worked in a lot of businesses where it's like, "No, no, we have to get more complicated. It's more complicated." And, you know, so I feel like I spend a lot of time now on how do you find the simplicity and the things that are true, and you can just drive against and get people to understand and really continue to focus on for a number of years, right?

(Joel Beasley at 00:32:35) I love that, and I agree with that 100%. It takes a long time to figure that out.

(Rob Ransom at 00:32:42) Took me a long time. Yeah. No, yeah.

(Joel Beasley at 00:32:45) Yeah, it took me a while, but I found it in business when I was starting, trying everything. You know, you're just scrambling. You're drowning. You know, you're out there just splashing around. And then I realized after, you know, years of doing that, that there's really only two or three things on my plate every year, and it's more sales, better product. Yeah. So I either sit down as an engineer—I'm working on my sales process, making that better, making the experience better all the way through from the sale to delivery—or I'm making the product itself better. I'm getting more listeners. The clips are better. We're organizing the content creation and deployment process. But every day I wake up and I'm like, "Okay, I'm either working on improving the sales function or I'm working on improving the product." And I found that if I just spend all of my time on those two things, then it just works.

(Rob Ransom at 00:33:41) Yeah. Yeah. That's a great example. I think I'll hold up Booking.com as sort of the organizational example too. You know, what really built the business is Booking.com stayed focused on accommodations, and in particular hotels, for almost two decades. That focus was very, very powerful. Right? And so it just allowed Booking to say, "Hey, we're going to make all these improvements. We improve the service, serve our customers better, expand to new geographies, serve more customers." And it's like, "Okay, well, we're going to be done next year, and then we can move on to something else." And you realize, well, you're never done. There's always more to do. There's always more improvements, either things the teams are thinking of, things our customers are asking for, et cetera. And so literally you could just keep going. And then two decades later, you realize, "Wow, we're just really focused." But now we're a big global organization, very successful doing that. And, you know, it's just a great lesson of, "Wow, it's not like it didn't occur to them to say, 'Hey, maybe we should offer some other things.'" But, you know, leadership at those moments said, "Hey, you know what? Let's just stay focused and see. Let's make what we're doing better." It just worked out really well, right? And so it's a great example. I find it inspiring when we're thinking about some of these earlier stage businesses. How do you just stay focused? And I'm someone who loves new ideas and new things, and so I'm always trying to prevent myself from getting distracted on new ideas. I love that stuff, but the best thing for the company and the business is often keep doing what you're doing and just do it better.

(Joel Beasley at 00:35:19) It's always easier to make it more complicated. It's always the most difficult to keep it simple, and you can even find this in art. Like, I talked to this famous music producer once. I was like, "How do you know when the song's done?" Like, because you add all the tracks. He goes, "You know it's done when you're done removing stuff." And I was like, "Oh." He's like, "Yeah, you overproduce and you start removing stuff." And I was like, "Oh, wow, okay." Because you can always sit down and add another layer of paint to make the picture more complicated. You have to know the art is almost knowing when to stop. Yeah. And when to scrape.

(Rob Ransom at 00:35:52) Yeah, how you find the essence. Yeah. That makes sense.

(Joel Beasley at 00:35:55) Do you find yourself as the head of strategy helping the other components of the business with this? Like, if I were to talk to some of your peers, would they tell me, like, "Rob's always keeping us realigning us, getting us back on focus"?

(Rob Ransom at 00:36:10) Well, I would hope they would say that. I don't know. We could arrange that. I do think we—you know, and I don't want to sound naive about it—we run a big complex organization and a big complex industry, and there's a lot of complexity in our business, right? So it is, but how do you find that simplicity? How do you focus on the things that are really going to matter? And so I do try and do that. I also, when we're just developing people on the teams who are earlier in their careers and things like that—and by definition, they're going to be more in the details of a particular product or initiative, something like that, and you need to understand those details. We've all been there. But then it's like, "Okay, how do you take that and bring that up and bring that up to be able to find the one or two or three things that really matter from that product, that initiative, et cetera, and how you're going to find success going forward?" So I do find more and more focusing on that. Like, let's distill this down to those couple of points and really take that home.

(Joel Beasley at 00:37:08) I want to talk about mistakes. People always can learn. We got the next generation of tech leaders listening in, and they can always learn from mistakes. And so what's the biggest leadership mistake that you've made?

(Rob Ransom at 00:37:22) I think there was one. You know, I described to you earlier when I joined Booking.com, we had acquired a couple startups. I joined the business. And these were—I just described how Booking.com was so focused for almost two decades, right? And this was one of the first initiatives to say, "Hey, this is really outside our core business," and it's new. And I was new to the organization, and it was really the CEO at the time who thought that this was an initiative they wanted to back, you know, did some acquisitions and brought me in. And I think my biggest leadership mistake was I was assuming because the CEO was behind this idea that the whole organization was just going to jump and rally, and this was great, and everyone was supportive, and we're going to align and make this happen. And that was wrong. Naive, right? And it got me in trouble because you end up making assumptions about what's going to happen and how things are going to work. And in a big company or even a smaller one, you need your peers, your colleagues, your other parts of the organization to understand what you're doing, to be willing to help directly or indirectly, all of those things. And so that was a tough one because it wasn't so obvious. It wasn't obvious that I was making that mistake. It's very obvious to me in hindsight. In the moment, I didn't—obviously, if I'd known that I was making that mistake, I would have tried to fix it sooner. But that was very clear to me, and so a very big lesson that, "Hey, whatever you need to do, you need to get people understanding what you're doing, why you're doing it, how it's going to help them or help the business together." Very obvious. But, you know, I was leading a pretty large team and a lot of people, and we had a lot of resources, and I just wasn't understanding that. So that's really shaped how I do things ever since.

(Joel Beasley at 00:39:22) Now a lot of people, I'm sure, they're listening, they're technology leaders, and they're hearing you speak. And you sound like a technology leader who just happens to have a corporate strategy title. They might be interested in moving into corporate strategy, becoming, you know, maybe a career change, something like that. How would you—would you give anyone advice? Is there any advice for maybe CTOs? They've been running the product organization. They've been running the technology side of the business for a while, and they are interested in getting into strategy. Maybe they're getting purchased or just got acquired or something like that. How would they make that transition?

(Rob Ransom at 00:40:01) Yeah, it's a really interesting question. And first of all, I don't know how I sound like that. I'm not an engineer, all right? I like to joke, I've never written a line of code in my life. But I do like working with engineers. I think, you know, and, you know, maybe the connection there is I do think of myself as a problem solver, right? And engineering is fundamentally about, "Hey, let's find out new and creative ways to solve problems out there," whether those are business problems, technical problems, or both. So that's where I find that connection. In terms of—I think, you know, for folks who do have the technical background, the expertise, the understanding to move into the strategy side, the commercial side is very powerful. And there's lots of examples in tech of where the senior leadership, founders, CEOs, you know, have the engineering background. But at a big organization, I think the way—you know, to me, where I see it's valuable is it is hard to do strategy and technology. You understand where things are headed, what the technology enables, but then be able to connect that to customer needs and business models and things like that, right? And so, obviously, there's some people who maybe think hard about the business side, and they just don't understand the technology and therefore don't have a good sense of where things are headed or what's going to be possible tomorrow that's not possible today, right? So if you have that technical sense, the way to do it is you've got to think about the business too. Think about the customer. Think about what's possible. How does this enable it? If you're more early in your career, I love models where—and I think we would like to do more of this—where you pull someone in, an engineering manager who's maybe experienced at running a team or a product, but maybe doesn't have that, to come into a strategy team or a commercial team for a couple years almost as a rotation and say, "Hey, you're going to get exposure to a different way to think about problems, think about issues, maybe understand finances or things in ways you haven't before." And that combination is really powerful. So if you can find ways to get that exposure, I'm going to rotate into the strategy team for two or three years knowing that that's not necessarily my long-term future, but I'm going to build a skill set and a toolkit, right, that I can then go apply somewhere else. That's a very powerful way to do it.

(Joel Beasley at 00:42:20) Well, you know, I got excited about this interview because when I read that you'd gone from marketing to product strategy, what I would bet money—if I'm going to, because I do all this interview prep. I've done a thousand episodes. So I see the prep and then I talk to the person. And whenever I see that—like, different parts of the business, they were here, they were at SDR, then they went over to IT, then they were in product—whenever I see those people, I would bet money that they're going to the top. For some reason, that exposure to the different aspects of the business gives them this unique view that somehow is giving them the right stuff, and they just shoot up to the top. And for me, it's really exciting to see that pattern because it's pretty rare, Rob. Like, I don't—it's not like everyday stories. It's like maybe one in 50 or something like that of the number of interviews I do. But when I see it, it's awesome.

(Rob Ransom at 00:43:13) Oh, it's an interesting perspective. I think the one thing that I've seen with people is that if you have that sense that, "Hey, either you've got that learner mindset or you want to really understand other parts of other functions," the thing that people need to let go of to do that, and some people just aren't wired to let go, is you need to let go of having real predictability about where your career is headed then, right? Because some people say, "Hey, I know I want—I'm a developer one. I'm going to be a two, and then I'm going to be a manager, and then I'm a lead, and I can see that path," right? But if you say, "Now I'm going to switch to marketing, and then I might go into customer service, and then—and I have no idea where that's going to end up." And some people love that. They think that maybe is exciting, but other people are like, "Yeah, I don't—that feels scary, and therefore I'm not going to do it," right? So you've got to be willing to take that leap a little bit, I think.

(Joel Beasley at 00:44:07) I have a higher than normal risk tolerance, like, than the general population.

(Rob Ransom at 00:44:11) Yeah. Yeah. That—it'll—

(Joel Beasley at 00:44:13) It'll all work out. We'll figure it out. We'll go over here. But there is this—I get it too. And that's the trade-off on certainty, like certainty with their path versus risk. Some people have different levels, and it's not wrong, it's not right. It's just what's right for you. And that's where, Rob, self-awareness comes in, right? Because that's a big thing.

(Rob Ransom at 00:44:37) It's different risk tolerance, and by—you know, obviously it's things like where you are in your life, right? You might make a—you might be at a certain moment in your life, in your personal life, whatever, that you've got a different view on things. And a few years later, you're in a very different place, and you make a different set of decisions, and that's all good too, right? Like you said, you know, everyone's got their own path.

(Joel Beasley at 00:44:56) Well, Rob, we did it, man. We made a podcast. How do you feel?

(Rob Ransom at 00:45:00) All right, I feel great.

(Joel Beasley at 00:45:02) Thank you so much for listening, and if you found this episode useful, please share it with a friend or colleague who you think would get value from it. And if you have topics that you'd like to hear discussed on the podcast, either add me on LinkedIn or send me an email: [email protected]. Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.