The Modern Hotelier #146: Digital Strategies that Drive Direct Bookings | with Charlie Osmond
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Steve Carran: Welcome to another episode of the Modern Hotelier. Today, we're excited to bring you our conversation with Charlie Osmond, the co founder of Triptease. David, what were some of your favorite takeaways from this conversation?
David Millili: Charlie was really interesting guy, very diverse background. even just the fact of being in the British army and things of that nature, but you know, really his passion and what Triptease is doing around just helping hotels get direct bookings, which is what everyone's been talking about. But it's kind of cool to see somebody who's like their whole company and their whole passion has just been about helping hotels, even, you know, their direct booking summit.
I mean, you can't be any more direct than that.
Steve Carran: Absolutely. Absolutely. I mean, this guy, he's an entrepreneur. that's all he's done is start his own companies after college. He founded two companies within five months of each other, which is pretty crazy. And then, you know, he wanted to get into, get into the travel industry just because of pain that he felt during the booking process.
and I love what Triptease is doing. David, we talk to hotels often. One of the topics we hear all the time is we need to help drive more direct bookings. You know, OTAs are taking too much. love to see what Triptease is doing and I'm excited to follow their journey and see them at the direct booking summit, but enjoy the episode.
David Millili: Enjoy it.

David Millili: Welcome to the modern hotel. Your hospitality is most engaged podcast. I'm David Malili.
Steve Carran: I'm Steve Karin.
Jon Bumhoffer: And I'm John Boomhoffer.
David Millili: who do we have on the program today?
Steve Carran: Yeah, David. Today we have on Charlie Osmond. Charlie is the co founder of Triptease. He is a seasoned entrepreneur and inventor renowned for his significant contributions to the fields of hospitality technology and social media marketing. Triptease is a leader in the direct booking movement, providing tools and insights that empower hotels to compete with OTAs and maximize revenue.
Welcome to the show, Charlie.
Charlie Osmond: Hello. Thank you for the intro.
Steve Carran: You bet.
David Millili: So we're going to go through a couple areas. We're going to go through a lightning round. We're going to ask you quick questions. We're going to get to know a little bit about you, your personal background, your career, and then we're going to jump into some industry topics.
Sound good.
Charlie Osmond: Excellent. Yes.
David Millili: All right. What's something that you wish you were better at?
Charlie Osmond: Managing people, 
David Millili: All right.
Charlie Osmond: that's like a key to so much success. I definitely wish I could improve that. I can give you a long list. I've got a lot of things on that list, but that'll start. How's
David Millili: right. Good. All right. What's the most used app on your phone?
Charlie Osmond: Oh, I mean, that would be Chrome, if you actually really want it, but otherwise, Google maps, I guess these days so
David Millili: What's a luxury you can't live without,
Charlie Osmond: running shoes, good quality running shoes
David Millili: right? this is a tough one. If you could trade places with someone for a day, who would you trade places with?
Charlie Osmond: one day, it's hard not to be political and think it would be something to do with the Russia Ukraine war and maybe Vladimir Putin for the day, try and change a few things. I think that would be it. Have an impact in a day.
David Millili: That's good. What's the best piece of advice you've received?
Charlie Osmond: Oh, my first boss, Peter Slater at Unilever, who was a fabulous man. And, he knew that I was, when I left university, I was going to do a startup. And his one bit of advice to me was make sure you pick, the best clients. If you work with really good customers, they will force you to be better. And so I held that one in my head for the next 20 years, I guess, and went out and tried to do exactly that.
David Millili: city and why?
Charlie Osmond: I have to say London. I mean, I do love New York City, which is where I live, but, I think then that keeps me out of London. And so then when I get back to bits of London, it just makes me feel very at home and special.
Steve Carran: That's great. That's great. Now we're going to go into your background a little bit more about what makes you tick. So you said now you live in New York City, but you grew up in the UK. Is that right?
Charlie Osmond: Yes,
Steve Carran: Where in the UK did you grow up?
Charlie Osmond: a little place called Chislehurst, which is in sort of greater London, about 11 miles. I guess, five o'clock, so if you head Southwest, 
Steve Carran: How did growing up there shape you into who you are today?
Charlie Osmond: again, now I compare myself to living in America and Americans. I'm a little more reserved, a little more cautious, maybe, sort of British traits. Yeah, I guess, that has an impact, but then equally, I felt like I always felt like we were very close to London and my family and we grew up very much always being taken to shows and, seeing things in the city and getting a feel for that, like energy of the city.
So I suspect that's also had an impact on me and made me feel like, Yeah, anything's possible.
David Millili: And so you graduated from the university of Oxford with a degree in engineering. What caused you to go to pick Oxford and what shows degree?
Charlie Osmond: if you want the deep and honest truth, it's probably because my brother went to Cambridge. that's, ultimately, he was only a year older than me, and sibling rivalry was always very strong. And, so I knew I couldn't follow his footsteps. We went to the same boarding school before that, so I had to go different.
and I remember that. And I remember my dad taking me there one day, which was his, I'd now know it was his effort to inspire me to actually start working at school. and so just seeing the place was beautiful. And so that did make me fall in love and think it was time at A levels to actually do some work.
I think it was those two things, right? So inspiration from my dad and needing to do something different from my brother.
Steve Carran: That's awesome. and this is probably one of the coolest things that I've found out while one of our guests did in college. You were part of the Oxford University Yacht Club. How did you get into yachting? And also any cool stories that you have while, being part of the yachting club?
Charlie Osmond: gosh, cool. I don't think of Yossi as that cool, but it really isn't sailing club. It's just got a more fancy title. I got into it from, I said a lot at school and it was a sport I really loved. and so I wanted to carry that on at university and there's, you know, it's great, a great way to, compete with other universities and lots of travel and stuff. I think the best for me, the thing that was actually best that came out of it was after university for like the 10 years after, there were four of us who sort of met at Oxford and sailed together and we then formed a match racing team.
So doing a match racing events around Europe, we'd sort of fly places and do those at the weekend. And that was, a really special. I guess extension of the university experience of just feeling like you're with friends going out and doing things, that, I'm always very grateful for. I really had a special time with those guys and we did, yeah, we did a lot of sailing and fun places.
Steve Carran: Awesome.
David Millili: That's great. And then you were also part of the British army and part of the SSLC with the 28th engineer regiment. Can you tell us about that experience?
Charlie Osmond: Yeah. okay. So gosh, these are great questions. Things I have dug up from my past. so when I was at school, the school actually has a history of, I guess often preparing people for the military. we don't have military service in the UK, which I think is probably a good thing, but I always really thought that joining the army would be great.
and I found out that there was this thing you could do where you join the army for one year between school and university. And you become an officer. So you go to Sandhurst, which is where we do officer training in the UK, and in the British army. And you go to Sandhurst for a month and become an officer and you get sent out to regiment.
So I was sent to regiment in Germany, for the year. And I always wanted to do it cause I just thought it'd be really good leadership training. I always knew I wanted to be an entrepreneur. I knew I wanted to run my own business. I knew that's kind of the way I was going to head off to university.
And I just, I was looking for opportunities to learn things. So my internships were all very specific things I wanted to learn about business I thought the British army would be great fun. and also really good for sort of leadership training. So that's why I decided, yeah, spend a year in the army.
And it was, really fabulous time.
Steve Carran: I could ask a follow up question because I feel like some of the most, I don't want to say most successful people we've had on, but a lot of leaders in the hospitality industry do have a military background or have some type of military influence in their life. what do you take from the, that year that you spent in the military that you still take today with you as?
Co founder of Triptease.
Charlie Osmond: I make my bed in the morning. No, that's not true. there's a bunch of things I got out of it. It gave me incredible respect for. people from all walks of life doing all sorts of jobs because it didn't matter whether you were, you know, the general or, the squaddy, the sort of the, junior soldier, the amount of care that people put into their, to their work, just really amazing.
Like it was, I was a school boy, right? I knew nothing. And I was thrown into this, regiment in the middle of Germany and just seeing the professionalism of people from all walks of life is something that's always stuck with me. and I think also just, it makes you sanguine. You know, you know that you can kind of.
You've been through a whole bunch of pain in, in various bits of the training, and you just kind of know whatever comes at you, just, you know, make plans, take action. If it works great. If it doesn't try something else and you just kind of get on with life. I think, I guess that's what it taught me a bit of.
Steve Carran: great. That's great. So now we're going to dive into your career, how you ended up at Triptease. So this is quite impressive. After college, you co founded two different companies. First was Decidedly, I believe. Then Fresh Minds Talent. Five months later after Decidedly. How did you start these companies?
And how did you start two within a year of each other?
Charlie Osmond: So it was, 2000. And I, like many of my friends in my course, university, the number one thing people went to do was consulting. And along with someone else I knew, we got job offers from McKinsey. We were going to become consultants. It seemed like the right track. It was the obvious thing to do after engineering in our kind of course.
but it was also dot com boom time. And it felt wow, this is just such a great time to start something. And guess what? Those jobs will be around. In a year's time, if you do a startup and it fails, what's the worst thing that can happen? you should be even better prepared to go take one of those sort of consulting jobs.
So we kind of felt like a zero risk option, at that time to just start something. So the two of us started and then we'd made the decision to start in sort of, I guess, February, March, 2000. Then you had the dot com bust, which happened around February, March, April. and everyone was like stopping doing online startups and, and dot com crash happened.
by the time we graduated, then it was like, okay, we decided we want to do a startup. We perhaps aren't going to do a dot com, won't do something on the web just yet. And we kind of realized what we had in our toolbox was we had a bunch of friends, who are really talented and capable, who are like still at university or who just left, had a year off, Who we knew were smart and capable and who we knew we could also hire for about 10 an hour.
and then on the flip side, we knew there was a market where people were paying these same kids, you know, 210 an hour. And it just felt wow, there's a massive discontinuity here. We can hire, we know how to go and find really smart, capable people who are, worth a lot more than, they know right now, and so let's join them up with companies to do research projects.
So basically we built a research analytics business, using a whole bunch of, friends and colleagues from university. selling research consultancy to companies. we did that for about four or five months before a load of the companies that saw us hiring people just said, actually, can you just hire us permanent people as well?
So just then, I mean, it was very early on. It, was really obvious that the core thing we had was an ability to tap into talent and find really capable people. And there were kind of two models that the market wanted to buy access to those people, either just by recruiting them or, hiring through us as consultants.
So that's why we set up. Basically we had the two companies run separately from that on.
Steve Carran: It's very cool.
Charlie Osmond: Yeah, it was fun. It was a lot of fun out of university. I, you know, looking back on it, I was, I kind of wish we hadn't done something like that because we started with 250 pounds of startup capital. So it was a very easy business to get going because you can get profitable very quickly.
but you know, with, hindsight, it would have been better to have actually gone for, it's a really bad time to start a. com, but starting something digital back then would have been better. So it then took us 10 years to then exit out of those two, then finally be able to do something new.
David Millili: also were co founder of Fresh Networks. So maybe can you take us through, you know, some of the successes and maybe even failures of being a founder that you've shared or you can actually has helped you when you co founded Triptease?
Charlie Osmond: it feels like a long time ago. I have to remember back my lessons of which there were many. I mean, you know, a few things jump out, right? So one, I had, I know a bunch of contemporary friends at university who always said, Oh, I'm going to do a startup one day. And 20 years on, I know that people and I can, and they're still working in corporate jobs.
And it's because they always would say to me, I'm going to wait for the perfect idea. And when I have the perfect idea, then I'm going to leave and do a startup. And I guess lesson number one for me was always, you have no idea what is a good idea. You just have to start something. You just got to start something.
And then you're in a market and you're meeting customers and you're then, you learn what people's real needs are, and then you might happen upon a good idea. and that's, you know, People talk about pivoting and all sorts of things these days, but back then no one was saying that, but it definitely is kind of a lesson that I think I still would encourage people who are who are feeling entrepreneurial.
Don't get too hung up about the idea because it's probably a bad one that you, that even the thing that convinces you to get going is probably not a great idea, but it doesn't matter. What matters is you start. that's the kind of number one. then the only other thing that matters after you've started is that you just hold on and don't give up.
I mean, within reason, right? There are times where it's right to, or you need a very major pivot but ultimately, if you can just keep on seeing the next day, then you can keep on building customers and keep on growing and sort of find a way through. So both with, you know, Triptease we had two years of chasing the wrong idea before finally kind of working out what it was.
it's just a lot of iteration and you've got to be prepared to, what is it? Chew on, glass. I think, Elon Musk wants to put it as, you know, just, keep on going.
Steve Carran: absolutely. So like you said, in 2013, you co founded Triptease. What gave you the idea and what was that final push where you're like, okay, we're going to start this company.
Charlie Osmond: so I'm, it's almost worth saying there's two different bits to it because Whilst first of all, I was, I wanted to exit from my last company. I wanted, to finally do the thing that I felt I was trained for, which was like an engineer. I want to do something digital. That was kind of why I'd originally started, but we fell into two of the companies that were growing well.
So it was very hard to extricate ourselves. So one was like, I want to, do something online. The second one was at that travel was I think over 40 percent of all online commerce travel was very like an early adoption, a sense of people spending money and getting their credit cards out online versus clothing and all the other things.
And, the furniture that people would buy today. so one travel was a very big part of e commerce and then the other ones, I just had a personal pain point. I realized the single thing that I most. hated in life was planning summer, planning my family trip every year. because it seemed that for, you know, seven day trip or a six day holiday, I was spending four, two day weekends, like fully immersed in the planning process.
And I was like, this is more time planning and stress than it is on the trip. And it just really upset me. I didn't understand how. Something that's, that ought to be, that deserves to be so delightful as travel felt so painful to me. I'm sure there are other people who love the planning phase, but I just found it so agonizing.
The, will I pick the right hotel? Will it, is it at the best price? All these pain points. I just didn't understand. How can you know, the biggest thing, biggest industry on the internet at the time, We ought to give you pleasure. That's part of why you travel be so painful.
And I just thought I've just got to try and do something to fix this. This is something I would like to dedicate my next decade to. And so that was kind of, that was my starting point was right. Let's dive in. And then it was a case of, what's the, what are the opportunities within it? And, The original idea for Triptease and why it has the strange name that it has is, actually was around another thought we had was, it seemed very strange at that moment that the most impactful social media on, at the time online was, TripAdvisor reviews.
And I say impactful because TripAdvisor reviews back in 2012 would make people make a decision to book a holiday, right? Book a hotel. So they were really impactful. It was social media. People were sharing and creating content and that content was having a real impact. And so you had that on one side and then on the other side, the other sort of thing we saw in social media back then, a lot of was, People sharing travel photos on, say, Facebook.
So at the time, the most shared content on Facebook were travel photos. and we know the biggest impact that, you know, you have from social was, like in triple revi reviews. And yet those two things didn't kind of meet. And it was, it seems strange. You would never You'd never go share a review you wrote on TripAdvisor.
and you'd never book a hotel just because you saw it on, Facebook at that time. So it was like, what's the opportunity to, do something here? So in fact, Triptease started as an iPad app where you would create and share a review and tease your friends. And then we'd put into that app like a little, if you book this hotel direct, you get a discount.
So there was kind of like a, An incentive to share. And it, felt a bit li a little bit like Instagram when you, when you first created one of these travel reviews, you felt a bit like, wow, I've made something worthy of Conde NAS Travel magazine. It looks amazing. and so we really kind of focused on that and it was great.
And we did this for a year and a half, apple. we're going to roll it out onto into the, as a key app, one of the four apps that you'd see when you're in the app in an Apple store looking at iPads, because they thought it looked beautiful and people really loved it.
But then we realized it was just going to be really hard to scale. Consumer. B2C travel was kind of already won by booking an Expedia and it just felt just too difficult. So we then made a pivot after a while and went B2B and focused much more on how do we help hotels drive direct. 
David Millili: so let's, kind of keep going with that. So those who might not be familiar with Triptease, maybe just explain what Triptease is doing today and how it's helping hotels.
Charlie Osmond: Yeah, so Going through that experience with the, first capability, the thing, one of the things we noticed was that, whenever we said to a hotel, Hey, would you like to encourage guests to share this content? Cause it might drive direct bookings. Their eyes lit up when you said the phrase direct bookings.
And so it felt ah, that's the pain point. You know, we can be solving for, hotels are finding it increasingly challenging to get people to book direct. was research after study that showed guests prefer to book hotels direct and yet very often at the last minute, were then choosing the OTAs.
there was a real, like fear amongst hotels that the costs of, Commission payments to OTAs were going up year after year at double the speed that the hotel's revenues were growing. So it was like this really scary growing cost. And also, the hotel's becoming reliant on OTAs. It's very easy, I think, to get lazy.
Let the OTAs do your distribution and then just become reliant on it. So all of those things told us, okay, there's a problem here. A lot of people go into the hotel business because they love, Caring for people and creating great moments of joy, face to face human contact. Not because necessarily they're great at digital marketing, or, building online websites or booking engines.
So it just occurred to us, you know, or it felt like this is an area where hotels need real help. It's never ending because every year there are changes in the digital marketplace that mean you need to kind of keep up with it. And again, that, that makes it hard for hotels versus OTAs who have. teams of people to do it.
So I just felt okay, there's a real need here, real opportunity. I personally prefer to book direct. so this is something I kind of feel aligned with. So it was like, great, this is a great area to jump in and help hotels improve their digital presence, improve their direct bookings.
Steve Carran: fantastic. That's great. So now we're going to dive into the industry thoughts part of this, where we get to get your take on some of the things that are happening in the hospitality industry. So one thing that we talk about a lot on this podcast, and that's been a challenge for hotels is competing with OTAs.
How can hotels kind of reclaim that guest experience and drive more direct bookings?
Charlie Osmond: there are so many different ways to solve that. So I think my starting point, It's always parity because it's just the symbol. It's the single most important thing to get right. and, I feel like a broken record cause it's all I've said for 10 years and yet it remains true. the way I think about it is guests have to make two decisions.
The first decision is where do I want to go? like what hotel do I want to stay at? And then there's a second separate decision that a guest is making, which is what channel am I going to book that hotel on? And it is really worth having in your mind. Those are two separate decisions. Usually it's two separate moments or often two separate moments.
So there's a whole bunch of things you need to do in digital marketing to woo the perfect guest and get them to want your hotel. But there's a separate moment where it, you know, for most people, right? The average guest is they've already been to the website. Senior on OTAs, if senior in many places, it's 30 days into their booking process, and they go, I'm going to book right now.
And at that moment, the set of things that the guest is doing, and the things that determine whether they're going to book on your channel are like be worth being really clear on. And so at that moment, the one thing, the key driver is, parity Most guests are most likely to be, persuaded to book where the cheapest rate is.
And you know, it doesn't matter everything else you do, you can invest a huge fortune in all your advertising, but they're going to go choose the channel based on the price generally. And so that's why Parity is kind of number one. and yeah, that's, it's, kind of simple and obvious, but it's, it remains difficult to do.
so I think. Parity is a tough challenge. And then you could argue, why, is parity a tough challenge? I mean, it's a tough challenge, one, because the OTAs know they only have to beat you by a dollar to get the booking. If they beat you by a dollar and they get, they charge you 20 percent, then, you know, they could be making really great money for being just like breaking parity that little bit.
So it's hard for that reason. and it's hard also, I think because of alignment within hotels. and I think this is, I think this is definitely improving over the last few years, but you know, the fact that a director of sales might have a target, that means they just want to sign up a third party distributors.
They just want to get as much revenue as they can through there. Whereas the head of e commerce is like focused on, I want to drive people direct. so you have these like competing goals, within the hotel that drives tension and often drives bad contracts, static rates and other things that just mean it's harder to have piracy, it's hardest to win direct.
I mean, we've gone for about, for a while about what really drives it. So anyway, but, piracy's one. The next one, which is in my mind, cause I just actually, I just, before the call had a quick look. Every month I get a report, of all the, cause we, we have thousands of hotels and we're tracking bookings, conversions, benchmarks across thousands of different hotels on hundreds of different booking engines.
one of the reports I get every month is like the top 20 booking engines. What are the conversion rates we see across all the hotels on them? And this is the top 20. Booking engines, right? Not then the next 180 that we also work with, just the top 20. From that top 20, there are, you know, booking engines, which are doing double the conversion rates of others.
So even if you pick one of the very best booking engines, they could have a really big difference between really, did get one of the top. 5, 6, 7 booking engines or the ones below. It can literally be half your, direct bookings gone from that decision. So I think, you know, being really clear, what else is it that Booking and Expedia do really is they make that checkout flow really 
David Millili: Yeah. 
Charlie Osmond: And I'm afraid to say that even many of the big name booking engines Just don't, it's just a little bit awkward and being just a little bit awkward me or the cash is a bit slow or, you know, booking from a certain country. It's a bit slow. That just means that someone's going to go book directly via a different channel.
I want to be specific. So I had a quick look and I would say just again, having a look, just had a look at the top 20 for the last month. If your booking engine conversion rate. So when someone is on the booking engine, running a rate search is less than 6%. You should be considering whether there are better booking engines to move to.
If on desktop, if your booking engine conversion rate is less than two and a half percent on mobile, you should be considering whether there's better booking engines to move to. So I mean, that kind of means you'd have to be in one of the top 10 out of 200, but like you just should be, because if you haven't got a really nice, easy booking flow, all the money you spend on the advertising not goes out the window, but it's just, it's, you're then having to spend again on the commissions to the OTAs and you're paying twice for the same guest.
Steve Carran: That was great.
David Millili: Yeah. that's a very good
advice. 
Charlie Osmond: if anyone wants specific, things that, you know, we don't release the data for cross booking engines, but if someone wants to get in touch with me directly, then I'm very happy to provide advice on whether, you know, they're performing underperforming or doing really well against benchmarks.
David Millili: yeah, I'm going to have some questions for you when we're done. All right. So with AI and machine learning, really shaping all industries, shaping the world, how is Triptease leveraging these new technologies to help enhance the booking experience? Yeah. Yeah. Yeah.
Charlie Osmond: so I think in a few different ways. So one, let me just talk about, getting guests to the book engine, to the website, the right guests, the right audiences. So one of the things we've invested a lot in recently is not just, okay, how do I drive traffic, but how do I. You know, identify for me as a hotel and it's different, whatever hotel you're in.
I'm a hotel in Washington today. and the kind of guests they would get this part of Washington is no doubt very different from other parts. but for your property or properties, what are the most valuable audiences? Which are the guests who are going to be most value to you? And how do I go and attract audiences like that?
And that's, a question that like we spent, I say a lot of time on is What are the things that you can understand or intuit about your most valuable guests, your most valuable bookers that can define audience segments that then you can go and target. And so using AI to identify lookalike audiences, or really valuable audiences and being able to target them is one key thing that I know we've been investing in a bit.
another one, a bit like lower down the booking engine funnel is on meta search. and this is something we've, been doing for a while is all the meta bidding that we do, because it's that, you know, second decision, people are just deciding on the channel. all of that is done by AI, and algorithms because you just simply can't.
Manage, as a human, all of the million potential computations, right? Of should I invest, spending more on someone who's looking for these dates right now, with, this many nights, from this IP address, at this time of day based, given that our parity is really good, all of those different combinations and being able to come up with exactly the right amount to spend on that, guest.
It's just way too hard to do as a human. You don't have, you can't be crunching that much data that many times a day. So using AI and that bidding decision is like something we've spent a lot of time on and it seems really. we know is really powerful. and then sort of the final one right on the bottom of the funnel is, when we're looking at guests who are on the hotel website, booking engine is trying to understand really quickly based on someone's behavior, what's their propensity to convert, how likely is this guest right now to convert?
Are they at the top of the funnel? They researching, or are they like a booking phase? And based on that, you might want to deliver different. Personalized messaging. you might want to spend more or less money retargeting them based on the dates they're looking at and how likely that, how important those dates are to you, various different things.
yeah, I think there's a kind of three phases, three different bits of AI, but it's, you know, these days it's like a little bit in everything we're doing.
Steve Carran: That's, great. So what are you seeing that are some of the most common mistakes hotels are making with the digital booking experience and maybe what are one or two things that they can do to help improve?
Charlie Osmond: it's kind of an impossible question because we work with, because the hotels are in such different places, we have. independent hotel where they just don't have time resource to even think about digital and they kind of need to outsource everything and have a trusted partner who can do stuff for them.
And then you have others who have a digital team of 20 and, they're like fine tuning their, algorithm for things. one thing that I feel over the last couple of years, we, it's become clearer to us and something we want to try and help the industry get over is I think because there are so many things you can do.
You know, if you're a hotelier today, the list of things you could do to help improve your digital marketing and the list of things that people will pitch you that you should do is so long. I feel like, hoteliers often get caught in channel first thinking. So it's kind of, okay, I need to do paid search.
I need to do meta search. I need to have an email. All these different channels have different providers. And as a result, it's very easy to get locked into optimizing individual channels. And so one of the things we're trying to help encourage is in a sense, returning to the basics that good marketing and hoteliers sort of, you know, know intuitively, of who are the most valuable guests or audiences or segments for my hotel.
And that changes over time and at different times of year. if I want to target those audiences, then what are the campaigns that are most likely to speak to those audiences? Then after you've done that, then you can say, okay, and how do I do that across multiple channels at once? And so I think shifting from that, okay, what can I be doing to improve by five points my meta search to actually know who the audiences I'm trying to target, what are the campaigns gonna be and how do I, you know, make those campaigns run multi across multiple channels at once?
I think that shift is probably one of the things that. We're trying to encourage hotels to do more at the moment.
David Millili: And so I guess another question that I have is how can hotels balance some of the automation while maintaining, you know, the personal touch with the guest and the guest interactions online
Charlie Osmond: okay. I'm not a hotelier. I'm no expert on, hotel, guest interface and experience. So I, caveat everything I say with that. I guess, I mean, the obvious bit is obviously choosing what to automate, what automate well.
For me, I guess the. The things that make, I travel a lot, I spend a lot of time in hotels. Whether it's the booking the hotel or whether it's arriving in a hotel or being in a hotel, it really does come down to that truism. I'm sure there's a lot of research that shows it, like you remember the last moment of an experience and you remember the highlight of an experience.
It's so true but those kind of like magic moments really stand out. I, you know, I can think of those times where I've walked into a lobby, in fact I walked into a different hotel a week ago and The people behind the front desk couldn't have been less interested in me if they tried. I mean, they really, it was like, I was struggling with the door with my, there were no interest compare that to another hotel I've walked into where they run out from the front desk to try and help you bring your bags and you like the welcome.
So the hotel starts at the door, not at the desk. when I think about moments like that or moments where. The next morning, someone on the front desk remembers your name or says your name to you and you're like, wow, that's really impressive. Those magic moments. I think wherever automation can help you help enable those magic moments, You know, it could be a really good thing to consider. I don't think it, yeah, it doesn't have to replace them, but feeling and being recognized just is like such a special part of travel, isn't it? That I guess that's kind of, and that recognition can happen on the website. It can happen in a WhatsApp, it can happen face to face.
So I guess that's probably where I'd be. Looking to put my automations.
Steve Carran: this is our final question here on this section, and I gotta get your thoughts on this. If you could change one thing about the way hotels approach their digital strategy, or maybe one you would give hotels to improve their digital strategy, what would it be?
Charlie Osmond: Oh, okay. if it's one tip, it is, this is, it's not just hotels. I find this is the same thing. I try to coach people on when they join our business, I think it's just. it's a standard thing throughout life. People often end up, I find, You know, whatever job you're in, it can be very easy to end up with a fixed, quite constrained view of the world of, okay, this is the thing I'm trying to achieve.
And maybe this touches a little bit back when I was saying about channels, like we, kind of over time, narrow our focus a little bit And the number one thing when it comes to driving more direct bookings is to experience the experience from the eyes of the guests. It's so simple.
It's such a simple, easy thing. And yet I find it's 5 or 10 percent of people who really do it. Like when we pitch hotels, Oh, we can do this for you. We could do that. The conversations I love is when they say, wait, hold on a second. Walk me through the experience as if I'm a guest. you know, you've told me you could do this whiz bang thing, just be like, treat me like an idiot or a five year old walk me through the experience.
What is going to happen? What is that going to be like? How is that going to feel? And it's the people who take themselves out of their own head and just kind of imagine walking through it. And in our business, when we're changing lots, as we do on what are the wording that someone's going to see when they see an advert?
What is the imagery or the wording they're going to see when they arrive on the hotel website? You know, again, the. The best in our business are the ones who go, okay, imagine I'm a guest and they, you know, I'm going to walk through this website experience. I'm actually going to say it aloud sometimes because it kind of helps me remember I'm trying to act out as a certain persona.
I'm going to say what I see and say how it makes me feel. And that's going to help me really, walk in the shoes of the person who's living the experience. I think that's it. Sorry that was a very long winded way of saying have empathy.
Steve Carran: That's great. I love walking in the customer's shoes. That's a kind of taking a step back a little bit. that was great. Charlie, this whole time we've been asking you the questions. So now we're going to turn the tables and we're going to let you ask David and I a question.
Charlie Osmond: when you think of the people you've worked with, who you admire and learn something from, can you pick out like an individual and a trait or a skill that like someone had where you're like, oh my god, I wish I had that capability this person has.
I really admire it.
David Millili: I've had, you know, a friend who, I won't say who it is, but they just really had a very, Very unique way of identifying who a person was by just having a conversation with them, almost like their soul. Like he kind of knew they were a good person.
They were going to be a hard worker. They were going to be energetic or something of that nature. And, I think sometimes I'm too optimistic. and I'm always looking for the best sometimes. And as I get older, I think maybe I'm, shifting towards. What he can do, but he can just talk to somebody and tell you something.
And then you're like, Oh my God, how did this guy know that? Cause it'll come true like nine out of 10 times, you know, what he says the person is like, or what their issue is or things of that nature. So that was something that was unique that I really liked about that person.
Charlie Osmond: That is a magic skill. That is a good one.
Steve Carran: there's a few people in my life who, have this skill, but, earlier in the week while I was watching a Kobe Bryant documentary, and the one thing that kind of stuck out is the same trait and it's just the focus. And vision that some people have, you can tear your Achilles like Kobe did.
And he's I'm not going to go down like this, no matter what I'm going to get back up or, you know, I've been in sales my whole life, you know, you have a bad month, you have a bad quarter. And it's just I don't care. I am going to succeed no matter what is in front of me and no matter, what obstacles have come my way.
I'm a very emotional person. You can tell when I'm really happy. You can tell when I'm not. but those people just are able to stay focused, not let anything deter them, not get down in the dumps or sad or upset. they get upset a little bit few times, but you know, Keep that focus and that mentality of just a laser focus on their goals.
So I've always been impressed with people that can do that. Like whether the storms, no matter what happens, and they're always going to come out the other side and succeed.
Charlie Osmond: Great.
Steve Carran: I feel well, that's great. That was a great question, Charlie. What one of our one of our better ones. Well done. and now we are down to the final question for you.
Our producer, John, he has been listening in this whole time. So we're going to kick it over to him. For the final question and then we're gonna get you out of here.
Jon Bumhoffer: All right. So it's been a really fun listening to the conversation. it seems to me like you have a very open mind of learning and growing. So I'm wondering what are some things you learned this last year and what are the things like you're doubling down on? Like you, you believe in it and you're doubling down on it again this year.
And maybe what's one thing that you have changed your mind about.
Charlie Osmond: you have a really good microphone, John. really nice to listen to you. okay. the, so one thing this year that I'm like doubling down even more on is, there's a problem that I guess has been very clear, to me in hotel tech for the last 10 years. I think clear to more people for longer than me, of data silos and things being caught up in different tools.
And for many, I remember eight, nine years ago, we first tried to integrate with opera. Oh my God, it was painful and gave up. and so I just put it off for six years. We can't do that again. and it's a real shame, right? You know, people say the PMS is where data goes to die sometimes. I don't know.
I'm not specific PMSs, but whatever the, there's a real, downside to hoteliers having data locked up in systems that don't talk to each other. and. For a while, I think we, I was thinking about, okay, proper integrations is what you need. And then it just felt when, I then dug below the surface of different integrations out there, you often find they didn't really deliver everything you hoped.
Some just because one system's integrated with another didn't really necessarily mean the data you thought they were going to share is what was shared. So one of the things that has been most delightful about, the AI, changes over the last couple of years is the growth of no code AI agents.
And so we've really doubled down on actually lightweight ways to integrate, data from across different systems, and how hotels can do that. And so in fact, I started doing a few like YouTube videos on. Here's how you can pull data out of your demand 360 and turn it into reports or push it into your marketing systems or pull data from your revenue management system and push it into what, you know, something that's going to send out an email automatically from your CRM.
Looking for things that aren't our engineering team, our product engineering team, building, you know, the scalable system that 20, 000 hotels can use, but that's encouraged hoteliers to build some of their own systems, which is maybe counter to the business of being a software provider in the industry, but I just think it's.
Where this industry has to go, is don't wait anymore for partners necessarily to deliver the integration you've been waiting for five years. You can now just do it yourself and you can do it yourself with no code tools that you can learn in about 24 hours. And so I think I want to like really help showcase that.
and I want to help make sure the industry like embraces that over the next 12 can be a massive change, 12 months from now. So I think that's the one thing. So it's maybe different to what I thought a year ago. I don't think it quite perfectly answers your question of something that was a change in my view, but I get it.
It's an evolution because I didn't think it was possible a year ago.
David Millili: that does it for another episode of the Modern Hotelier. I'd like to, myself and my team would like to thank you, Charlie, and your team for offering to work with us for the direct booking summit coming up in May. so we're very excited about that, but this is the part of the program where you can tell people more about the summit, more about Triptees and how people can get in touch with you.
Charlie Osmond: Oh yeah. Okay. direct booking summit back, to the USA in, May. So just a couple of months to go, we will be in Dallas, and there will be hundreds of hoteliers. it's a event very much focused on hoteliers sharing their experiences. This is not a You know, Tripti is what's our new product, pitch.
In fact, we usually get told we don't do enough of that stuff. the goal is to have on stage, hoteliers where we've identified, because maybe they're customers. Okay, here's someone who's really done something amazing because the direct bookings doubled last year. What did they do? And they come and talk through, here are the five different things we did.
and we try and have independent hotels with one property and we have mid market groups with a hundred, properties, talking about. the different things they're doing in various different bits of marketing, to help drive direct. So it's like the number one focused event on the planet, on direct bookings, and it's all about sharing tips and practical, things that you as a hotelier can implement.
So if driving direct is in your strategy, it's something you're trying to do, and you have a target around it. There is no better place on earth to learn from other hotels and what's worked and also what hasn't worked, than the direct booking summit.
Steve Carran: Sounds like every hotel should be there. Looking forward to it.
Charlie Osmond: Great. Thank you.
David Millili: that does it for another episode of the Modern Hotelier, Hospitality's Most Engaged Podcast. So whether you're watching or listening, we appreciate you and we'll see you again soon. Thank you, Charlie.