[00:00:00] Charlie Osmond: Either you’ve got your data sorted and it’s really high quality and you’re going to be driving outstanding decisions, or you’ve got a data mess and you’re just driving the wrong decisions consistently all the time.

[00:00:11] Karen Stephens: Welcome to the Hotel Moment podcast presented by Revinate. I’m Karen Stephens, Chief Marketing Officer, joining you from sunny San Francisco, California.

[00:00:19] Dylan Cole: And I’m Dylan Cole, Managing Director of Revinate Europe, calling in from Amsterdam.

[00:00:24] Karen Stephens: This is the podcast where we explore how technology shapes every moment of the hotelier’s experience and, more importantly, how the right technology delivers real outcomes for hotel teams and guests alike.

[00:00:34] Dylan Cole: From revenue strategy and guest communication to operations and marketing, we sit down with the people transforming hospitality around the world.

[00:00:43] Karen Stephens: Depending on the conversation, sometimes it’ll just be me behind the mic.

[00:00:47] Dylan Cole: And sometimes it’ll be me bringing a European perspective and stories from across the global hospitality industry.

[00:00:53] Karen Stephens: Whether you’re a hotelier, a tech enthusiast, or just curious about where hospitality is headed.

[00:00:57] Dylan Cole: You’re in the right place. Let’s get into it. Welcome to Hotel Moment. Today, we’re joined by Charlie Osmond, co-founder of Triptease, the leading platform helping hotels grow direct bookings through personalization and smarter use of guest data. Since founding Triptease in 2013, Charlie has worked closely with hoteliers around the world to understand how guests shop, book, and make decisions online. With AI now reshaping the booking journey and acting as a new middle layer between guests and hotels, Charlie brings a clear, practical perspective on how hotels can stay visible, protect revenue, and use clean data to their advantage rather than losing control to intermediaries. What I loved about today’s conversation with Charlie is that he’s seen the evolution of hotels utilizing their data since his founding of Triptease. He’s seen it where vendors were locking down the data, not making it available to hoteliers, to today where vendors actually lead their business strategy on making data available to hoteliers, which is ultimately important when you think about AI and being able to power the tools that run on data. So today’s conversation, we’ll dig into that and some other topics, but it’s a good one. Hey, before we get into AI and the booking journey, I think it’s good we take a little step outside of hospitality maybe for a second. We know you’ve run a lot of marathons in a lot of places that most people have never even traveled before. We’re all curious what kind of draws you into those challenges, and does that mindset show up in how you’ve built and grown Triptease?

[00:02:34] Charlie Osmond: I always promised myself I’d never run a marathon. I thought it was like, bad for your knees. And then when I moved to New York, I accidentally entered the New York Marathon and got an invite. And so I did it, and it changed everything for me. The main thing, I guess I found that after running one, if you want to run more, everyone kind of has the same ones they want to do. Everyone kind of — I realized I wanted specifically to go in a different path. So I looked for — my goal was to find a marathon I could win. That was the first goal. And I was like, I have to travel to pretty far away places to go and do that. So Kazakhstan, North Korea. I haven’t won one yet, but a couple times. But yeah, just I think I find it more fun to use it as a way to explore parts of the Earth I wouldn’t get to otherwise.

[00:03:15] Dylan Cole: That’s really cool. North Korea, huh?

[00:03:17] Charlie Osmond: Yeah, that was mental.

[00:03:19] Dylan Cole: That’s wild. Cool. Well, I guess sort of shifting then more towards Triptease and hospitality, but still like curious about your passion. So you’ve obviously been a bit obsessed with how guests behave online, especially that moment where they decide to book. So I guess what originally fascinated you with that decision point, and how has that insight or that kind of obsession shaped the way you’ve built Triptease over time?

[00:03:46] Charlie Osmond: So I’ve always been interested in behavioral psychology, like why people do things. I think that’s just always been inherent in me and how marketing and messaging relates to that. But really the kind of — the original idea of Triptease came from personal struggle and pain. I realized that the single thing in my life that made me most upset and unhappy each year was planning travel. I couldn’t understand how if I was going to go away with my family for six days, I seemed to spend four weekends’ worth of work just doing the planning for it. It just didn’t make any sense. And I found it so frustrating that given the time — so it seems a while ago now, like over 10 years ago — travel was by far the number one thing people spend money on online. And it was like the biggest online industry then. And yet it was such a clunky, horrible experience. And it just felt like there’s a problem there that I wanted to go solve for myself and everyone else.

[00:04:38] Dylan Cole: Yeah, it was challenging. When you were booking your North Korea marathon trip, actually…

[00:04:44] Charlie Osmond: …that gets really easy because there’s only one way in. There’s only — I’m doing the official tour. You don’t get to make it because they track you around the country, you have to always be with someone. You can’t ever go out anywhere on your own.

[00:04:54] Dylan Cole: Right. There’s only one way to book that trip. Well, cool. So thanks for sharing that. I guess moving into sort of today’s world, AI is becoming increasingly the middleman in the booking journey. We’re seeing that; we’re all seeing that. So from your perspective, how real is the risk for hotels to lose control over the guest relationship kind of as AI-driven conversations start to replace more traditional discovery and booking paths?

[00:05:20] Charlie Osmond: So I don’t think it’s a risk of losing the guest relationship. After all, like, the best place for the guest relationship to flourish is on site and on property. In terms of losing it during the marketing experience, yeah, I think there’s a risk of that. My overall — I feel pretty excited about what lies ahead in terms of the direct channel, because I actually think the OTAs are the ones who are more likely to get disrupted and challenged, not in the short term, but I think in the midterm. And everything that I see month after month in terms of innovations in AI and agents and the way people use them leads me to feel we’re heading more and more in that way where the individual hotelier, the individual website can do better. So actually, overall, I kind of see it as a good thing. I think there are loads of ways in which there’s a risk that the hotelier loses insight, information, data about guests who are doing things on their website, what they’re interested in, where they’re going to buy. So there’s a load of signals, but I think most hoteliers aren’t actually using those signals very well at all, if at all, today anyway. And I think there’s ways to replace them. So there are things that we can do that actually allow us, when interacting with an agent, to actually almost learn more about a guest than the guest would tell us if they were just on the hotel website. And some of the evolutions recently we’ve seen just in the last few months with WebMCP, I think lead us to a place where that’s possible. So I’m really excited about actually there’s going to be more data and more to be able to grab and more interactions and more ways to personalize in the future than there are even today.

[00:06:55] Dylan Cole: Right. But we got to be at the forefront of that and got to be thinking about how to actually not take a backseat to it, but make sure that we’re investing and thinking about how to be at the forefront of it. And I guess what does that shift mean for hotels, and what do they need to be thinking about now in terms of visibility and differentiation going forward if those, again, two things — discovery and booking — are kind of collapsing into one flow?

[00:07:23] Charlie Osmond: Yeah, I think the first thing that’s worth saying is there is massive shifts happening and coming, but right now in 2026, fewer than like 1 or 2% of bookings are going to come to you from ChatGPT. Now it might be partly involved in some of the upstream recommendations and initial thinking, but you know, you’re not actually going to get many bookings in 2026 from it and it’s not going to change that much behavior. I think that’s worth always stipulating before we go down the exciting, high-hype changes. The other thing worth — is there are many different customer types, and it will be undoubtedly even five years from now there will be certain customer groups or certain trip types where going to the website, having a full website experience, seeing images and the like is going to still remain something that people really want to do. So I think there’s not just one type of guest. Anyway, having said all that, yes, huge changes afoot and I think very exciting ones, not least because one of the sort of purposes of an agent kind of needs to be to deliver against the needs of the individual user. And in terms of delivering individual needs, you know, that comes down to personalization and really understanding what are the hot buttons, what are the things for this particular guest, what are they looking for, what makes one hotel great for them but not for another person. And so when I think about like that’s really what the agents are trying to — going to be solving, because if they can’t do that well, people won’t use them, right? So they have to be delivering what each individual guest wants. So with that in mind, it actually to me makes me think, well, there’s again even more deliberate desire to go and understand different properties, who they are great for, and in what circumstances. And so I guess that kind of brings me a little bit into your world of thinking. Part of the opportunity today and going forwards, I think, is that more than ever, understanding your ideal guest profile or your key persona — maybe it’s like five to ten different key types of guests that for your property, absolutely, always have a great time, get what they want in what they kind of expect and desire from a stay, and maybe from a hotel point of view also have big spenders one way or another. So that core set of personas, being able to really clearly articulate that, having the data internally, but also that you can make external about like why you fit for these people, I think leads to a really exciting kind of future for hotels because the agents are trying to understand what are the personas that fit: “Is the guy I’ve got who’s asking me questions going to be right for this hotel?” And so being able to have that data and then articulate that back to agents, I think is really exciting. So yes, there’s this kind of collapsing, but it doesn’t mean there isn’t a need for even more data interactions and flowing between the different systems.

[00:10:03] Dylan Cole: Definitely. And I guess that does lead me into my next question, which you’ve sort of answered right now. But as you start to see — well, I guess what I should say is we’ve seen you be pretty vocal about unified clean data, which you’ve just said now that’s been a big thing that you’ve always pushed, and I think why our companies have such synergy and we’ll continue to have even more over time. But as the journey kind of simplifies — and I know I’m recognizing what you just said, it’s not completely merged, there’s still a lot of nuance to it — but as the journey simplifies and these things come together, what do you think starts to break first in the guest journey when data is siloed or unreliable or when it’s dirty? Like, where do you think hotels start to see the impact of not doing that right immediately?

[00:10:54] Charlie Osmond: That’s a really interesting, challenging way to think about it. So I guess perhaps I’ll break it into two different sides. So first of all, one of the things we help hotels do is have really great data-driven marketing that brings the right people to the website. So if that data isn’t good and if that data isn’t real-time, then your ability to optimize advertising spend and to get really effective and efficient ads massively diminishes. So for example, one of the things that we see as absolutely critical when you’re bidding on a metasearch is you need to know: does the hotel for this itinerary right now have the best price? If the hotel has the best price, you bid very differently for that person running a search versus if the hotel doesn’t. If the hotel’s being beaten by Booking.com by a dollar, completely different bidding strategy, completely different ROI by knowing that data and having that data. So your ability — and that scales in many different ways — but your ability to have really effective advertising is instantly hit if the data’s not good. And then when it comes to actually how about like converting people or getting the right people to book on your hotel? I think that’s another really interesting area where, yes, things are collapsing, but that doesn’t mean there isn’t an increased opportunity to use data to both help the guest booker book the right hotel and help the hotel persuade the right kind of guests to stay there. And so I think that again, if you are not clear and precise and accurate with your data, then either you’re going to be telling agents who are out there looking for hotels that your hotel’s right for everyone, which then means it’s not right for anyone and that’s kind of useless, so not being defined. Or you’re going to define the wrong ICP and the wrong personas are going to be targeted, in which case you’re going to get people coming to the website who aren’t going to be very happy, not prepared to pay as much, don’t spend as much on F&B when they’re on the property. So in a sense, it’s almost like not having much of a brand, right? You have a brand that stands for something and then you’ll attract the right kind of people to it, and obviously you’ll lose some people who aren’t then right for it. Or you have a brand that kind of stands for nothing and you just kind of are in a sea of mediocrity. You’re like a price on a pin on a map. And that’s not a great place to be, I think, for the hotelier. So yeah, I think you need that data to inform, get the right kind of people to be interested in the hotel, and make sure that they book, too.

[00:13:05] Dylan Cole: I think when we go to — let’s say we’ll be at, you know, we’ll be at ITB next month, and the word AI will be everywhere, I’m sure of it. But at the end of the day, if the data behind the scenes isn’t clean and unified, then all of your great plans for it will not come to fruition. I think one of the stories that Bryson tells — for those who don’t know Bryson, Revinate’s CEO — tells often, he talks about this grocery store that had this idea for an AI agent that could recommend recipes for you based on their inventory in the store. Well, they didn’t map it very well, and all of a sudden the thing was recommending Windex mixed with spaghetti sauce mixed with toothpaste. So it’s like again, the idea can be great, but if the data behind it isn’t appropriately mapped or set up or unified, then, you know…

[00:13:55] Charlie Osmond: Yeah, I mean, I think data’s always been important to be able to make decisions and move forwards. I feel like in an ever-accelerating AI world it only becomes more important — not like a little bit more important, but like 10x, 100x, 1,000x. We now have the ability for systems to be making so many more nuanced calculations and decisions that either you’ve got your data sorted and it’s really high quality and you’re going to be driving outstanding decisions, or you’ve got a data mess and you’re just driving the wrong decisions consistently all the time. So the speed and opportunity to be pulling different data from different systems is like never before, and the ability to then apply intelligence to that in the form of LLMs to make decisions for you is like never before. There’s only going to be an acceleration of that. But if what’s going in at the beginning is rubbish, then you’re in a really bad place. And it’s something actually I kind of worry about a bit in the industry because I don’t know about you and your experience, but when we were starting up the business like 12 years ago, we wanted to get an integration with Oracle Opera back then, and they made it so hard and so expensive. And it felt like to me and all the other entrepreneurs and founders who were doing stuff in hotel tech as we spoke about what we were doing, we just could see that the whole industry was held back because there were some players in the industry who wanted to hold onto their data or wanted to run a payment or a costing system for it that meant it just wasn’t feasible for innovation to happen.

[00:15:20] Dylan Cole: And you mean from the hotelier side, by the way, right? With the PMS?

[00:15:24] Charlie Osmond: Exactly, those licenses. Exactly. And so we’re not here just to have a go at Oracle. I really want to call it out because that’s a decade or more that we went through as an industry where we really slowed down innovation. Now they saw it, I guess — you mentioned Mews, right? They saw Mews, Apaleo, and others coming and they realized they had to open up their APIs, and they’ve done a really good job of that. So well done to them. They’ve changed the business model; they found other ways to charge, which means innovation is now possible. But my God, did we suffer for 15, 20 years. And my worry today, with again like that accelerating value and importance of data, is that because for other reasons now there are other incumbents who are putting their arms around their own data, worried about it — or they’ve been bought by private equity who’s saying, “We want blood out of the stone,” or they’re nervous because we’ve all seen in the last few months software businesses freaking out, losing their share price because what’s the future of a software business if AI is going to vibe code everything for you? — so suddenly these other software businesses in our industry are like getting scared about, well, where are we going to make money? And they’re making APIs — well, not available. They’re making APIs, but they’re putting prices on them that are so high because they see that this might be the only way to sustain their revenues. Again, I’m worried that in this moment where the data should be released, where the opportunity is vast, that actually we’ll be held back because there are certain players who are fighting a business model that they just want to maintain. And the reason I guess I bring this up is because I think hoteliers, they do these RFPs — “What’s my booking engine, my CRS going to be?” whatever — and they perhaps don’t spend enough time asking the question, “How do you as a vendor charge other vendors? How open are your systems?” There has never been a more important time for that question and for forcing, pushing your CRS to give you like real data openness. So it’s one of my concerns. I feel like we could be held back and that’s the kind of thing that would mean the industry doesn’t take this opportunity to accelerate. Compared to say the OTAs, it’s actually that we individual vendors, one by one, lock down things.

[00:17:20] Dylan Cole: It’s really interesting. More recently in RFPs, we are starting to see people asking about that, but definitely not nearly enough. And maybe there wasn’t as many use cases for taking data out of a product like Revinate before, but we are starting to see more of it, which is good.

[00:17:34] Charlie Osmond: And don’t get me wrong, right, there’s really good reasons why vendors should be able to charge for some data feeds. Like if we push our data to Revinate, that’s valuable. If Revinate pushes data to us, that’s valuable. And it costs money for us to maintain those. But there’s like a standard rate. And then I’ve just seen some vendors out there in the last few months multiplying by 10 the rate of connectivity, and they’re really doing it to try and prevent people using the connection at all. And that’s just like backwards.

[00:17:58] Dylan Cole: No. And you’ve seen the way that Mews has been able to grow their business through being open and being available and making partners a big part of their play, and it’s all good. So, hey, shifting real quick, I think this is a good question. On top of this is as we think about AI-powered personalization and cleaner data — okay, we all know this sounds great, but like, are there any metrics that you have in mind that a hotelier should be thinking about to know that this investment in work is actually paying off for them?

[00:18:26] Charlie Osmond: I think the simplest way is you can run a marketing campaign, let’s say it’s an email campaign or a personalization campaign with some messages that you might put on your website. It’s really easy to send an email to your entire database and see what the click-through rate and the conversion rate and unsubscribe rate is. And it is really easy to do that when you target those segments a little bit. And you know, okay, these are the people who like golf, these are the people who come for Christmas, these are whatever. And you tailor those emails, and you see today extraordinary differences in open rate, click-through rate. Like, it’s a good question, but like we’ve solved for that already, right? Everybody believes it, don’t we know that if you give me something I’m interested in, I’m much more likely to remain subscribed, book, and the like. And I’ve seen Revinate data, I’m sure, that shows that you did that with emails, and we see the same when we personalize experiences on the website or in advertising.

[00:19:14] Dylan Cole: It’s human nature. And you’re right. Oh, I guess — so then to summarize kind of your point, it’s conversion rates, it’s click-through rates, it’s all of these things hopefully driving higher numbers on things that we’ve been doing for a long time. Is that a fair summary?

[00:19:32] Charlie Osmond: Yeah. And running the personalized campaign and comparing it to a non-personalized one, I think the results are very clear.

[00:19:38] Dylan Cole: So kind of future thinking as we sort of come to our final few questions, but looking at the next 12 to 18 months, what are the most practical steps a hotel can take right now to protect their direct revenue, kind of reduce leakage to OTAs, and I guess stay competitive as AI reshapes the booking journey as we know it?

[00:19:58] Charlie Osmond: Well, so the first things are probably the non-AI ones, because if it’s about wanting to have great performance the next 12 to 18 months, a lot of that comes down to doing the basics well. And I spoke to a hotelier yesterday who arrived in a business a year ago, and it was great because there were so many basic things to fix. And I hear that again and again. So I don’t want to go away from — like, there’s core things that you need. You need a website that is clean and updated and a booking engine that’s got a good flow, high conversion rates, and you have really good parity. Like, you’ve got to get those things in place. You’ve got to make sure that you’re presenting your price on metasearch and getting clicks there. Like, there’s some basics like that. In terms of being ready for AI, I mean, I think this has been really interesting because in the last year I feel like we’ve seen a few different key things vendors were trying to sell around AI, particularly as it addresses the guest booking journey. And our view was the things that were being pushed weren’t really ready for prime time yet and weren’t ready for most hotels to adopt. I mean, the obvious one, right, is ChatGPT brings out an app store and there are people out there saying, “Oh hey, hotelier, we’ll get you on ChatGPT, we’ll get you in the app store.” But what they fail to mention is the process is someone has to be in ChatGPT, they have to know to ask for the brand of the vendor, and then that has to like show the hotel. So it’s like no one’s doing that. It’s just not going to happen. And that’s two people a year; it’s just not worth investing in. So I feel like some of the innovations that were kind of like early last year were selling things that aren’t actually going to deliver any value. And another one I think is actually — I think maybe people would be surprised to hear this — is the tools that you can pay for that show whether you’re likely to be recommended. Like, it seems like a really sensible thing to do: “Am I going to be recommended? Can I work on my AEO so that I get more recommended?” But the accuracy of those is so poor that the data is more likely to lead you the wrong way than the right way. And I say poor because just one particular fact, right? If I go into ChatGPT and put in a request, first of all, it’s nothing like the keywords I used to use two years ago on Google. No one is using those six words in a search; we’re using 24 words on average. But secondly, the results I get in ChatGPT running a search are completely different. So if I use the API that ChatGPT feeds to all of these vendors who are doing thousands of searches a day, like they just give you completely different results. They run searches in a completely different way. So you’re looking at the wrong data. So I think that’s like where we’ve been. I feel like now, however, there’s more clarity and focusing on like obviously really good standard SEO behaviors, and we’re looking very carefully at now some of the MCP capabilities that you can put on your website, on your booking engine. So I think looking at solutions like SynXis and Nexus business, they’ve got now MCP, and I think that looking at whether or not agents are actually going to use those and seeing what the take-up over the next few months is, is one of the things that we’re watching out closely for.

[00:22:45] Dylan Cole: It’s really interesting. To your point, it’s hard to believe we’ve already lived through a lot of the — I mean, there’s just so much more development to happen and so much more to change over time. But we’ve already lived through some of the initial hype, some of it. And to your point, I think now we are getting a little bit more clarity on what actually matters, where should we spend the time? Because I think everybody had that initial push of like, “Oh my God, I’m not on ChatGPT, my business is going under.” But you’re right, there’s starting to be a little more clarity. Definitely a lot more to go.

[00:23:15] Charlie Osmond: Yeah, I would say it’s like the one thing that is coming back to where we started that you absolutely will get value from year after year after year in AI, if you start with it now, is improving the quality of your data. If you’re doing that, if you’re connecting up your systems — your PMS with your CRM, CDP, and more — and you’re making sure that you’re taking out duplicates, your ability to have the data that you need to power the AI systems of the future, like that’s the most important thing to focus on first.

[00:23:41] Dylan Cole: Thank you for that. And as a final question, I want to phrase this in a way like we have our old-school hotelier who wants to interact by shaking every guest’s hand coming through the door, does not love technology, sees it as a threat to the personal touch, right? What would you say to that hotelier that gives you the most optimism about this AI world we’re stepping into? And in terms of the guest experience, like what would you say to that hotelier to gain their favor in this new world we’re venturing into?

[00:24:18] Charlie Osmond: It’s interesting actually. I’m split. Like on one side to that traditional hotelier who may have a great brand where people really value personal relationships and customers who come back to the hotel every year, it might be that, you know, driving direct bookings, driving success in ChatGPT simply isn’t important for them because they’ve got like a brand and they’ve got experience — like a happy guest who talks to friends, and that’s how they get their business. So it might be that that old-school hotelier should stick to what they are doing, because it’s amazing and it’s the opposite of what everyone else is going to do. So like I don’t want to always tell everyone to follow the herd. But if they wanted to sort of embrace it and there was an option, I guess maybe one of the things I always think of is the way you just described that hotelier, right? They’re focused on their guests. I bet you that great hotelier treats people differently based on how they show up at the hotel. They look at them across the lobby and they think, “That person’s stressed,” or “That person’s happy,” or “That person needs a coffee,” or whatever it is. And they go and speak to each individual and personalize that experience, because that’s what we do as humans. We know it’s important. And so all we’re doing with AI is we finally have the tools where we can look for the data signals of each individual. Instead of walking through the lobby, like arriving on the hotel website, we can look for the signals and we have the ability with the computing power to make the decisions in a computer that hotelier is making naturally, instinctively. After 40 years of doing the job, we can now do that online in a way we couldn’t before because we can do it at scale and get to real one-to-one marketing in a way we couldn’t before. So it’s kind of we’re just doing what he does so well and we’re just trying to make it online.

[00:25:49] Dylan Cole: I think you nailed that question and I agree completely. So let him or her take care of the guests in the hotel and let AI and the great technology that’s being built do the same personalization online for you. I don’t want to summarize you, but I just did, and I think it’s a great point. So with that, we can wrap it up. But thank you so much for your time, Charlie, and I look forward to seeing you at ITB this year.

[00:26:14] Charlie Osmond: See you then.

[00:26:15] Dylan Cole: See ya.

[00:26:20] Karen Stephens: 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.