How to win direct bookings with AI search

What happens when guests stop scrolling through pages of search results and start asking AI where to stay? Hotels suddenly have a new audience to impress: the algorithms making the recommendations.

In this episode of Hotel Moment, Karen Stephens sits down with Jarrett Tomback, VP of Digital Strategy and CRM at Starwood Hotels, to explore how AI search is reshaping hotel discovery, direct bookings, and guest loyalty. From becoming the source of truth for AI platforms to building data foundations that drive visibility, they unpack what it takes to stand out in an AI-first world.

The future of search may be powered by AI, but bookings are still driven by trust, emotion, and great hospitality. Tune in to learn why data gets you recommended, but storytelling gets you booked.

Meet your host

Karen Stephens

As Chief Marketing Officer at Revinate, Karen is focused on driving long-term growth by building Revinate’s brand equity, product marketing, and customer acquisition strategies. Her deep connections with hospitality industry leaders play a key role in crafting strategic partnerships. Karen has more than 25 years of expertise in global hospitality technology and online distribution — including managing global accounts in travel and hospitality organizations such as Travelocity and lastminute.com

As the host of The Hotel Moment podcast, she interviews top players in the hospitality industry. Karen has been with Revinate for over 11 years, leading our global GTM teams. Her most recent transition was from Chief Revenue Officer, where she led the team in their highest booking quarter to date in Q4 2023.

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Transcript

[00:00:00] Jarrett Tomback: Building those knowledge bases on the direct side and being able to distribute those to the LLMs so that we are the source of truth and that they’re not turning to third parties to get their data is critical.

[00:00:17] Intro: Welcome to the Hotel Moment Podcast, presented by Revinate, the podcast where we discuss how hotel technology shapes every moment of the hotelier’s experience. Tune in as we explore the cutting-edge technology transforming the hospitality industry and hear from experts and visionaries shaping the future of guest experiences. Whether you’re a hotelier or a tech enthusiast, you’re in the right place. Let’s dive in and discover how we can elevate the art of hospitality together.

[00:00:45] Karen Stephens: Hello and welcome to the Hotel Moment podcast. I’m your host, Karen Stephens, the Chief Marketing Officer of Revinate. And today we are thrilled to have Jarrett Tomback, Vice President of Digital Strategy and CRM at Starwood Hotels, where he leads digital growth, guest engagement, and loyalty across brands like 1 Hotels, Baccarat Hotels and Resorts, and Treehouse Hotels. With a background spanning some of the most innovative lifestyle hospitality brands, Jarrett specializes in building purpose-driven guest experiences and using data and technology to deepen relationships and drive revenue. Most recently, he’s been at the center of rethinking loyalty through 1 Hotel’s Mission Membership, a program that blends personalization, sustainability, and meaningful guest engagement. So without further ado, here’s Jarrett. Jarrett Tomback, welcome to the podcast.

[00:01:35] Jarrett Tomback: Thank you for having me.

[00:01:37] Karen Stephens: Well, it’s a pleasure to have you here. I mean, I have to say the brands in your group are some of my favorite in the world. So can we just start by talking a little bit about Starwood Hotels and the brands that you oversee within that group?

[00:01:49] Jarrett Tomback: Absolutely. So Starwood Hotels is a global sustainable hotel brand management company. Our three brands are 1 Hotels, Baccarat Hotels, and Treehouse Hotels. And we currently have locations globally, so spanning everywhere from the United States to Europe, Asia Pacific, and more to come.

[00:02:13] Karen Stephens: That is so cool. So I’m familiar with 1 Hotels. I’ve seen the one in San Francisco. I’ve admired the one in Kauai from afar. But can you tell us a little bit about each brand? So 1 Hotels and then I’d love Baccarat and especially Treehouse. So what is kind of the focus of those brands?

[00:02:28] Jarrett Tomback: Yeah, so 1 Hotels is the brand that is the largest in our portfolio and that we started with. It is a sustainable, nature-inspired brand, luxury lifestyle brand. And we like to say that everything we do there is inspired by nature. So we take all of our cues from nature with that brand. And we have locations of 1 Hotels, like you said, in San Francisco, a flagship property, in Hanalei Bay in Kauai, New York, where we have two properties, South Beach, which many people know that property, but now also locations in Mayfair London, in Copenhagen, Melbourne most recently, and Tokyo we just opened.

[00:03:10] Karen Stephens: Wow, fantastic. Okay, great. And then Baccarat, I mean, that sounds very snazzy. So tell us a little bit about that brand.

[00:03:18] Jarrett Tomback: It is. That one is. So Baccarat obviously builds on the amazing 250-year-plus history of the Baccarat crystal brand out of France. And we’re fortunate enough to work with that brand and bring that to life in the hospitality space. So our first Baccarat property is in New York. And we have more in the pipeline, which is very exciting. But for those who have experienced the Baccarat Hotel in New York, there are certainly a lot of sparkle and brilliant moments within that experience.

[00:03:48] Karen Stephens: Very cool. And then last but not least, Treehouse Hotels. So this just, I mean, just by the name on the tin. So what is Treehouse Hotels about?

[00:03:55] Jarrett Tomback: Yes, Treehouse is a very fun brand. We talk about carefreedom with this brand, and that’s really the feeling that we want people to have when they step into a Treehouse hotel. It’s a feeling of nostalgia and sort of that childhood wonder that we all experienced if we were lucky enough to have treehouses as a child, but even if we didn’t, it’s really that feeling of exploration and, again, sort of adventure for people who are young of all ages.

[00:04:23] Karen Stephens: I love that. Okay. Well, Jarrett, you know, so you’re working with Starwood Hotels now, but your career has been spent building some of the most distinctive lifestyle brands in hospitality. So when you look back, what originally drew you to the intersection of brand, guest experience, and also technology? What got you started?

[00:04:41] Jarrett Tomback: Yeah, so I’ve always had a passion for travel. I remember I grew up in Arizona and had lots of trips to Las Vegas when I was younger, and just the scale and the experience of Vegas hospitality and everything that encompassed within a single property was so sort of overwhelming and inspiring to me that it’s just something that drew me to this industry. And I was fortunate enough out of college to have an opportunity to go into a hospitality role. I started out in marketing really across hotels, restaurants, nightlife, and events, and so had an opportunity to get exposure to all aspects of hospitality. And, you know, over the years as marketing became increasingly digital, that was really where I was able to sort of hone my chops in the digital space and grow into roles that focused more and more on the digital experience, both from a marketing standpoint and from a guest experience standpoint. So that’s sort of been my journey to where I am today.

[00:05:43] Karen Stephens: Yeah, it’s so cool. And again, going back to the beautiful brands that you represent, what a gift as a digital marketer to have, you know, just the visual assets alone when you’re trying to talk about these properties, where they sit, how they work, what they are. So that’s a real treasure. The other thing I really want to dig into is the loyalty program because you’ve really rethought this on a whole new level. So let’s start with the 1 Hotels Mission Membership. So it’s a clear departure from traditional points-based loyalty programs. So what is the core problem you’re trying to solve or achieve by thinking in this way? Can you give us a little bit of an idea of that program?

[00:06:19] Jarrett Tomback: Yeah, absolutely. So several years ago, when we thought about loyalty and what that meant to the 1 Hotels brand and to Starwood Hotel’s more broadly, we really understood that our traveler, our consumer, is not necessarily the points chaser, right? And there’s certainly a lot of value to a lot of those big programs and many, many people who do enjoy those, but we really identified that our guest wanted personalization and they wanted to feel like they belong to something. And so that is where we came up with the idea of mission, and really positioning it as a membership and not a loyalty program. And we wanted people to feel like they belong to something and like there is a sense of purpose to why they stay with us, which is true for many of the 1 Hotels guests. Obviously, as a brand that cares deeply about nature and the planet, our guests do as well. And so we really wanted to bring that into our version of a loyalty program. So we launched, like you said, Mission Membership for 1 Hotels. This is our version, again, of loyalty, but it is really centered around the core mission of the brand, which is honoring, celebrating, and protecting nature. So guests who join—just for joining, first of all, we plant a tree, and then with every qualifying stay, we donate 1% of that revenue to their choice of one of our three nonprofit partners, which are the NRDC, Oceanic Global, and Green Our Planet. So with every stay, guests are giving back to nature in a way that they care about. With that, we also, of course, want to make sure that they’re getting real value out of it. So we invite members to tell us more about their preferences—not only for their room, but for the way they like to dine, for their experiences, their interests—and then our teams are able to use that to deliver much more personalized experiences to those guests. So it might be everything from a little surprise welcome amenity to the concierge being able to give them better recommendations during their stay based on their interests.

[00:08:29] Karen Stephens: You’re preaching to the choir over here. I mean, when it comes to guest experience, I think you’ve nailed it. And what a beautiful concept. Because obviously, like you said, you’ve already got the sustainability going. That’s kind of the mission of 1 Hotels as a brand, and then to extend that to the guests to let them feel like they’re right from the jump delivering more value. And then you’re personalizing that stay. So that’s something, you know, that we at Revinate, that’s what we sing from the rooftops all the time. So can you tell us, like, how are you using the data? How do you collect that data, and how do you use it with CRM to create those experiences so that it’s running properly on the back end, but it’s seamless for the guest on the front?

[00:09:09] Jarrett Tomback: Yeah, so this was a big investment that we made several years ago to really rethink the guest journey, again, around CRM and how we could capture more understanding of our guests to be able to deliver these kinds of experiences to them and really that sits at the core of how we’re able to deliver the entire guest journey. And so, both in terms of the data that we ask of members and guests directly in terms of their preferences, but also the things that our teams are able to observe. So if a guest, you know, we know is requesting extra pillows on every stay, that’s something that we want to note so that it’s there for them on their next stay without them having to request it the next time. So we’re able to take inputs from a number of sources. We also integrate various sources within our CRM. So we’re able to know that if there was a preference that they shared with us when they dined one time, maybe in their local market, that will still be reflected on their hotel portfolio as well, so that the next time they come stay, we make sure that perhaps the amenity that we deliver is based on something that they told us during one of their dining experiences. So it’s really about being able to get a comprehensive 360-degree view of the guest and their behaviors, their preferences, what they tell us directionally and observationally.

[00:10:30] Karen Stephens: Very cool. So I’m going to switch gears and talk a little bit about what everybody’s talking about, which is artificial intelligence. So you can’t walk out of the house without hearing about it today. So it’s becoming a bigger part of how hotels communicate and personalize. Where do you see AI playing the most meaningful role in the guest journey today? And where’s it being overhyped? Because we like to talk about that too.

[00:10:54] Jarrett Tomback: Yes, both valid. So we’re very excited about the potential of AI, but our approach at Starwood is really that it is human-first, powered by AI. So we look at AI as an opportunity to amplify what our amazing teams and team members are able to do in terms of delivering personalized hospitality to our guests. So some of the aspects that we’re looking at with AI are really things that the guests would never see. They’re back-of-house processes that, again, enable our teams to not have to do some of those mundane tasks that do pull them away from being able to spend time in front of the guests, and free them up to do the things that they’re really amazing at, which is delivering that kind of experience to our guests. But there are some areas that we are exploring guest-facing as well. There are, I think, opportunities that can make the guest experience more seamless if guests want to pursue them. So it might be things like an AI chat interface for things like concierge recommendations, seamless bookings. Of course, if somebody wants to reach out to a team member directly, they’re always going to be able to do that. We never want to create a more challenging experience for guests, whether it’s AI voice, AI chat. And certainly AI personalization is an area that we see potential in as well. So again, those are things that the guest might not even necessarily notice, but there are applications where we can take what we know about the guests and use AI to deliver different content to them that is more personalized and meaningful.

[00:12:22] Karen Stephens: Absolutely. You know, I think that this goes back to a CRM discussion in terms of making sure that your data is really as good as it can be, that you’ve got profiles that are synthesized, that you know who the guest is, you understand the preferences. Because if you have that, then AI can be applied to it and be effective. If the core data is incorrect, you’re going to get it wrong and then it becomes an annoyance, right? Or something, right? So that’s not great.

[00:12:47] Jarrett Tomback: And I think that’s something that a lot of companies are sort of learning as they have sprinted into different AI applications, particularly ones that are guest-facing, is, like you said, if the data house isn’t in order, if that foundation isn’t there, then the AI is going to be a worse experience than no AI at all. So that’s something that we’re really focused on is how do we make sure that our data is clean and actionable so that we are able to then apply it in AI. And that’s where we certainly tread carefully when it comes to guest-facing applications and spend a little bit more time, in the meantime, on some of those back-of-house applications.

[00:13:21] Karen Stephens: Yeah, it’s worth it. You don’t want AI hallucinating.

[00:13:24] Jarrett Tomback: Exactly. It’s very confidently wrong when it’s wrong.

[00:13:27] Karen Stephens: That’s right. That’s right. So let’s talk a little bit about channel strategy. So channel management, what I mean by that is distribution channels. So it’s becoming more complex now because now, in addition to everything that we’ve had traditionally, you also have AI, you have chatbots. So it’s becoming more complex with loyalty, personalization, distribution. Where do you see the biggest revenue leakage happening today across channels? And how can hotels gain more control of that?

[00:13:54] Jarrett Tomback: Yeah, so I think the ongoing challenge obviously continues to be, and the focus of a lot of brands is, how do we drive more direct, not only because it is the lowest acquisition cost, but also truly the best experience for guests to be able to interact and have that direct relationship with the guest. But I do think we’re at a pretty pivotal time, as you said, with certainly with AI having implications for distribution. I think there’s a lot that’s still to be determined in terms of what impact that’s going to have, but I also think that there’s a lot of potential for how that reshapes discovery and ultimately the booking process. I’m sure you saw, as we all did, Google’s announcement that their next focus for agentic commerce is in the hospitality space. So that’s exciting to see. But of course, with that, we want to make sure that as these new distribution channels open, we are able to drive as much direct as possible. And so I think that’s sort of the ongoing challenge. And certainly on the paid media side, we’ve only seen costs continue to increase and competition continue to increase. So focusing as much as we can on scaling back that component and being able to drive more direct is a focus for us, certainly.

[00:15:06] Karen Stephens: Absolutely. And when you think about Google and other LLMs getting into the space—well, who are in the space clearly—again, it comes down to who owns the data and the content. So that, I think, is the callout that we really try to evangelize at Revinate is that, hey, you own the guest experience, you own the guest data, you also know more about your hotels than anybody else does, so make sure you’ve got a way to interact with Google and others. You know, spoiler alert, we have a partnership with Google to help with some of that stuff because we’ve been in the market for so long. But we really think at this intersection, OTAs have such a breadth of content and obviously in a lot of different markets, but hotels still have the opportunity to get that distribution direct if the data is actionable and in the right place, if that makes sense.

[00:15:53] Jarrett Tomback: Absolutely. And that’s something that we’ve been working very diligently on over the past few months is the sort of AEO side of things. And you’re right, the brands do—we have the most data about our properties, but sometimes we give more of that to the OTAs than we even put out through our own sources of knowledge. So building those knowledge bases on the direct side and being able to distribute those to the LLMs so that we are the source of truth and that they’re not turning to third parties to get their data is critical.

[00:16:23] Karen Stephens: That’s right. You know, we had another guest on, Aaron Miller, who is over at Highgate. But we were just talking about how important it is—like what we also have as hoteliers or what you also have with your beautiful websites—is all the content. So if you can get that click-through and they come into your website, now the guests can really understand the experience that they’re going to be getting when they get on property. So more and more just comes back to just making sure that your visibility is there, and as you mentioned, it’s a moving target. I mean, it’s, you know, how does your team think about that? How are you adapting to that as kind of the head of the marketing team internally to kind of stay in front of those things?

[00:17:01] Jarrett Tomback: It is. And I think while the data is obviously the core of that and the key from, you know, an agentic LLM standpoint, the storytelling, like you said, is still where we’re able to have the most impact. And we do have these amazing brands that you really have to understand and, like you said, experience visually and know the meaning and the story behind these brands that really kind of gets taken away if it’s a pure data play. So we want to make sure that the data foundation is there so that the LLMs have all of the facts that they need to give the guests the correct answer and to recommend our properties, but then we do want to be able to drive them to the website where they really can immerse themselves in the brand experience and the brand story, because we think that’s what gives them the best understanding of what their stay experience will be like.

[00:17:51] Karen Stephens: Right. Because your holiday is one of the most important things. And I will stand by that over and over again, right? So okay. So the other fun thing we get to think about all the time as hoteliers and technology players in this space is data privacy. So we got a lot of data. We’ve got to make sure that that data stays protected. So data privacy has significantly reshaped how hotels use email and guest data. So what has your approach been to try and protect that and make sure the communication is on point? What is your approach to data privacy? I know you probably take it very seriously.

[00:18:23] Jarrett Tomback: We do, yes. This is, of course, of utmost importance to us as a company. We operate globally, so whether it’s the GDPR or increasingly individual state-by-state regulations that we’re experiencing, we have great counsel that works with us to make sure that we understand what those regulations are and that we’re not only compliant with the letter of the laws, but really taking the most conservative approach in terms of how we respect and utilize guest data.

[00:18:51] Karen Stephens: Yeah, it’s really important. So I’m glad to hear, obviously, you have that approach, but it’s something that bears repeating and reminding. So a couple more questions for you, Jarrett. So if a hotelier is listening to this episode and could take just one action this year to strengthen how they think about guest loyalty and drive more direct bookings, what would you recommend that they focus on?

[00:19:11] Jarrett Tomback: Yeah, I think the number one thing this year really is AEO—is AI search optimization. I do think that that is going to dramatically reshape the discovery and ultimately booking path for our guests. The traditional sort of blue links of Google—even they now are adjusting to an AI search first experience. And so, you know, in a world where an AI is really giving three to five recommendations and not pages and pages and pages of links, it is essential that you are in those top three to five recommendations based on the guest criteria of what they’re looking for. So I think that foundation is really critical for hoteliers this year.

[00:19:53] Karen Stephens: Absolutely. And last question for you. Looking ahead, how do you see the concept of loyalty evolving over the next five years, as guest expectations and technology and purpose continue to intersect?

[00:20:07] Jarrett Tomback: Yeah, I really think that guests increasingly are looking for a sense of purpose. They’re looking for brands that align with their values, that make them feel something, and that also say something about who they are. I think that loyalty is going to continue to evolve in that direction. And I also think that there’s an opportunity for hotel brands—and this is certainly something that we think about—to extend that experience and that feeling of membership beyond the stay. So, you know, when guests stay with us, it’s obviously they’re immersed in our world and our experience, but we do talk about lifestyle brands and we really want to make sure that that actually reflects in the guests’ lifestyle. So we think about how can we bring the experience that they might have with us in our properties to their day-to-day lives beyond the stay. And I think that’s an important area for brands to be thinking about when they think about loyalty.

[00:21:01] Karen Stephens: Great. Thank you, Jarrett. It’s been a real pleasure speaking with you, and wishing you all the best as we navigate this crazy world together. So thank you for your time.

[00:21:08] Jarrett Tomback: Exactly. Thank you, Karen.

[00:21:14] Outro: Thank you for joining us on this episode of Hotel Moment by Revinate. Our community of hoteliers is growing every week, and each guest we speak to is tackling industry challenges with the innovation and flexibility that our industry demands. If you enjoyed today’s episode, don’t forget to subscribe, rate, and leave a review. And if you’re listening on YouTube, please like the video and subscribe for more content. For more information, head to revinate.com/hotelmomentpodcast. Until next time, keep innovating.

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