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OTA Ranking Optimization Lessons From 25,000 Units and Counting with Bart-Jan Leyts

“Anyone could be ranked number one. Just slash your prices.”

That line from Bart-Jan Leyts sums up a trap many hosts fall into. Ranking first on Airbnb or Booking.com means nothing if your revenue goes backward. This episode of the Booked Solid Show is a little different. We usually talk about building your direct channel. This time, Gil sits across from someone who studies the other side of the table. Bart-Jan is the founder and CEO of Otamiser, an AI native revenue management service that handles OTA ranking optimization for over 25,000 units.

You’ll hear how Airbnb’s algorithm thinks differently from Booking.com and Expedia. Bart-Jan explains why a fully booked calendar can quietly hurt your ranking, and why owner stays and split calendars carry hidden costs. He also shares what conversational search means for your listings, and a simple fix for guests who copy your Airbnb title into Google and find nothing. Whether you run one cabin or a full portfolio, this one will change how you look at your listings. 🎧

Podcast and Summary Highlights

👤 About Bart-Jan Leyts

Bart-Jan Leyts is a 26 year old founder from Belgium and the CEO of Otamiser. He studied finance at Ghent University, and right after graduation he and his cofounders began doing hotel revenue management for family hotels and small chains across the Benelux region.

They noticed something early. A property’s dynamic pricing only worked as well as its position in search. That insight turned a small rate management side project into a company that now optimizes rankings and rates across Booking.com, Expedia, Airbnb, and Vrbo. Bart-Jan later brought the same thinking to short term rentals, starting with Casiola in Orlando and then launching a self serve tool called AutoRank. Today Otamiser blends software, AI agents, and hands on revenue managers into one service.

💡 Key Takeaways

🔁 Bookings, reviews, and consistency drive OTA rankings. Titles and photos help, but mainly as conversion accelerators.

📅 Booking pace matters more than most hosts think. Selling out all at once can stall your visibility.

🏡 Owner stays and calendars split across channels limit the inventory each OTA sees.

⭐ How you respond to a bad review can matter as much as the review itself.

🤖 Conversational search is coming to the OTAs, and listing accuracy will decide who gets shown.

🔍 If a guest pastes your Airbnb title into Google and can’t find you, you have an SEO problem.

🎯 Visibility Is Buying Bookings

Bart-Jan’s first experiment was simple. On Booking.com, his team joined the Preferred Partner program, which carries a higher commission. Then they raised rates to offset it. The result was net positive.

His takeaway? Guests don’t scroll far. They type one search with all their filters and book from the top. Expedia once told his team that roughly 75% of bookings go to the first 15 listings shown. More eyeballs really do buy more bookings.

That doesn’t mean chasing the top spot at any cost. As Bart-Jan points out, anyone can rank first by charging $10 a night. Ranking and revenue are not the same goal, which is why Otamiser ended up tying its ranking software directly to pricing. If you’ve been thinking about pricing as a standalone task, Mridul Bansal’s breakdown of the three signals behind dynamic pricing pairs nicely with this part of the conversation.

🧭 Two Kinds of OTAs, Two Different Games

Bart-Jan splits the OTA world in two. Booking.com and Expedia were built for hotels. Their algorithms favor the listings that will make the platform the most money, and paying more commission can move you up.

Airbnb and Vrbo are content OTAs. Their algorithm leans toward the listing that best matches the guest and is most likely to earn a strong review. That means your photos, descriptions, and settings carry more weight there. Vrbo sits somewhere in the middle.

He also notices the platforms drifting toward each other. Discounts that used to be a Booking.com specialty now show up on Airbnb and Vrbo too. For more on what’s shifting inside Airbnb specifically, Dan Rivers covered why Guest Favorite now outweighs Superhost in an earlier episode.

📅 The Hidden Cost of a Full Calendar

This was one of the most surprising parts of the episode. Bart-Jan ranks the top three factors as bookings, reviews, and consistency. Booking pace is the one he calls most underrated.

Some property managers sell out a listing’s whole calendar and celebrate. But once nothing is open, the platform stops indexing it. When dates open again, the listing practically starts over.

Owner stays work the same way. A month long owner block can hurt Airbnb rankings. And a listing split evenly between Airbnb and Vrbo shows each platform only half its availability. Bart-Jan doesn’t recommend going all in on one OTA though. A single suspension could take down the whole business. The answer is balance, which is also the heart of building a scalable direct booking strategy that doesn’t depend on any one channel.

⭐ Your Response Matters as Much as the Review

Every host gets a bad review eventually. Bart-Jan says what happens next is what counts. If guests complained about construction noise, updating your listing to say the work is finished helps Airbnb feel confident showing you again.

He also shares an honest observation about smaller hosts. They often rank higher, and many are exclusive to Airbnb. But Gil and Bart-Jan agree it’s more correlation than cause. Small hosts tend to describe every detail, down to the shampoo brand and the coffee maker. That care shows up in reviews. Vee Venski talked about a similar habit of tracking daily rank changes after every photo or title tweak.

🤖 Conversational Search Is Coming to the OTAs

Bart-Jan believes every OTA will move toward conversational search. Instead of filters, a guest might simply type, “I want a two bedroom home in Orlando.”

From tests run alongside people at Booking.com and Airbnb, one factor keeps rising to the top: listing accuracy. If your description says pets are welcome but your house rules say they aren’t, an AI model sees a contradiction. When it isn’t sure, it simply won’t show you.

His hypothesis for why this happens is relatable. As companies grow, many people touch each listing, and quality checks get lost along the way. He thinks a QA step inside your listing SOPs will soon be essential.

Gil notes the same shift on the direct side, where structured data and property schema now shape what AI tools can read. We covered that in what CraftedStays has been building for AI search and in our GEO framework for vacation rentals. Kin Sio’s episode on AI search visibility in the hotel funnel is another useful companion here.

🔗 Where OTA Visibility Meets Direct Bookings

Bart-Jan sees a natural spillover. Better OTA visibility often leads to more direct bookings too. Many guests find a listing on Airbnb, copy the title, and paste it into Google.

Here’s the catch. Most listings can’t be found that way. His fix is to treat your OTA title as an SEO asset. Some operators even run search ads on their own listing titles. The only people clicking are guests coming from an OTA, so the cost stays low.

Gil adds a lesson from his own early hosting. A generic property name leaves guests nothing to search for. A unique name works like a breadcrumb. Patryk Swietek made the same point about putting your brand into every OTA title, and it’s the whole idea behind the billboard effect. On CraftedStays, you can also seed those searchable phrases through per property SEO meta overrides.

⚡ Rapid Fire With Bart-Jan

📚 A book that shaped his career: Bart-Jan admits he doesn’t read many books. One that stuck was the Entrepreneurial Operating System (EOS), recommended to him by a property manager. It changed how he thinks about goal setting and keeping a company’s momentum.

🧠 Mindset advice for starting something new: Just do it. Test your idea small and see if it works. Otherwise you’ll spend years wondering what might have happened.

🛠️ One tactic to try this afternoon: Make your direct offer better than the OTA one. Early check in, free cancellation, a welcome basket, or a local perk like park discounts near Disney. Gil adds that it starts with knowing your ideal guest. Families may care most about flexible cancellation, while other travelers value an early check in. You can show that value right on your site with a direct booking price comparison.

🤝 Connect With Bart-Jan Leyts

🔗 LinkedIn: Bart-Jan Leyts

🌐 Website: Otamiser

🚀 Self serve tool: AutoRank

🎧 Listen, Connect, and Start Booking Direct

This recap only scratches the surface. In the full episode, Bart-Jan walks through how AI shortens the gap between spotting a trend and acting on it, how Otamiser works alongside the OTAs instead of against them, and what Airbnb’s newer commission experiments might signal. Hit play on the Booked Solid Show wherever you listen. 🎙️

And when guests go looking for you outside the OTAs, make sure they land somewhere worth booking. CraftedStays helps you build a fast, mobile first, SEO ready direct booking site that syncs with your PMS and converts the traffic you already have. 🏡 Build your brand. Start booking direct.

Transcription

Bart-Jan: We have seen after COVID that the guest journey, from opening your first search to booking, has become shorter and shorter. In every Booking.com, Expedia, and Airbnb report, year over year, they’re reporting shorter cycles between search and booking. Of course, this is not true for all verticals. For bigger homes and bigger families, that’s sometimes different, but in general, that’s the trend. Which is where different OTAs, and I assume all OTAs, will move into conversational search, where you will be able to go to Booking.com or Airbnb and type, “Hey, I want a two bedroom home in Orlando,” and that will be the query. The way of searching is about to change. It’s about to mimic conversational tools.

Gil: Before we bring on our guest, I wanted to talk a little bit about something I’ve been hearing a lot from hosts. I keep hearing the same thing: “I know my website isn’t converting, but I can’t afford $8,000 on an agency to rebuild it.” Here’s the thing. You’re learning all these marketing strategies, you’re driving traffic, and you’re putting it all to work, but if your site isn’t really built to convert, you’re basically lighting your energy and money on fire.

And even if you could afford an agency build, every time you want to test something or make a change, you have to pay them again. You can’t iterate, you can’t test, and you really can’t improve on things. You don’t need a custom $10,000 website to get the conversion rates that really matter. You just need the right platform.

That’s why I built CraftedStays. It’s purpose built for short term rentals and designed from the ground up to help you drive more direct bookings. You can finally turn that traffic into bookings, keep testing and improving as you learn, and make changes all on the platform. You don’t need to learn something new.

So if you need some help or you want to get started, go to craftedstays.co and start your free trial. Now let’s bring on our guest and dive deep into hospitality and marketing.

Hey folks, welcome back to the Booked Solid Show, the show where we bring in top operators to discuss hospitality, operations, and direct bookings.

On today’s show, we have Bart, the founder and CEO of Otamiser. This is going to be a little bit different. We spend a lot of time on this show talking about your direct channel, and Bart has built a company on the other side of the table, optimizing OTA rankings for over 25,000 units. We get to see how the Airbnb and Booking.com algorithms actually differ, what actually drives ranking, and what this means for your overall direct strategy.

So without further ado, let’s bring him in.

Gil: Hey, Bart. Welcome to the show.

Bart-Jan: Hey, Gil. Thanks for having me.

Gil: This is going to be interesting because we typically focus on building out your direct channel, and now we have you on the opposite end of the table, really optimizing for OTAs. So I’m really excited about today’s conversation, how you built the company, what problem you’re solving, and some of the things you’ve been seeing in the industry as you build and support your clients.

So to kick us off, Bart, do you mind giving folks an introduction on who you are?

Bart-Jan: I would very much love to. My name is Bart. I’m the founder and CEO of a company called Otamiser, based in Belgium. I’m 26, so I’ve been in this space for three years since the start of this company. We started our company with the vision that OTAs are there. They’re major sales channels for a lot of hospitality operators, but they are underutilized.

We wanted to fix that problem. After graduating from Ghent University, where some of the cofounders and I studied finance, we started doing hotel revenue management, optimizing rates for family hotels and smaller chains.

We quickly saw that the impact dynamic pricing could have was, A, dependent on data quality, which has rapidly evolved over the last three years, and B, dependent on where the property was found in search. We were talking about Europe, about Benelux. Booking.com was king there. So we saw that if a property ranked higher on Booking.com, it got more bookings, so it could be more elastic and more aggressive with ADR.

That’s when we turned our little three or four person hotel revenue management job into a company, back in June 2023, and we started creating algorithms. Algorithms to make sure that whenever one of the hotels we were managing was seen in search, it was seen higher than any of its competitors, meaning we could be more aggressive.

We got more of the specific demand for that property because we found, and this was later confirmed by the people at Expedia and Booking.com, that the higher you are in search, the more eyeballs, the more volume, and the more share of market demand you get to your listing.

Expedia once shared with us that 75% of all bookings go to the first 15 listings found in search, which is where we started building the algorithm, first for Booking.com, then for Expedia. So we were very focused on the hotel side of things. But then we got to know some people in the short term rental industry in Orlando, and they said, “Look, what you’re building for hotels, come and build it for us for short term rentals as well.”

We initially took over the whole revenue management and revenue strategy there, just to learn the nitty gritty of how short term rentals work, what the nuances are, and how you could actually rank higher on an OTA. It was a company called Casiola. Back then they were doing around 250 homes.

I think today they’re close to a thousand, if I’m not mistaken. This is where we learned everything for short term rentals, how you could rank higher on Airbnb, Vrbo, and all the surrounding platforms. Following that, we went to market with a different software as well. We were Otamiser, but we brought a software called AutoRank to market, where hosts and property managers could optimize their OTA listings themselves, automated, so they didn’t have to do it manually.

But then we quickly realized that the reason people come to us, wanting better OTA visibility, is not in sync with their end goal. The end goal was always that they wanted to make more money. They wanted higher revenue, and they wanted to grow the business.

So we saw that anyone could be ranked number one. If you just slash your prices and ask $10, you will be ranked number one because an OTA will see it as a gem and it will get booked. So we saw that ranking maximization and revenue maximization weren’t fully aligned.

That’s when we blended our software into our initial offering, and we went to market with a full revenue management service offering, with our unique edge and our in house OTA optimization software, now connected with rates. What is the impact of today’s rate change on your position tomorrow, how do you keep this flywheel going, and how do you make it a repeating process so you can make more money over time?

We went to market with this bundled offering at the end of 2025, and since then we’re still loving it and still growing. It’s a fun space.

Gil: So it sounds like you did a bit of both software and services, and perhaps the services side allowed you to understand the mechanics before you built out the software side. Please correct me if that assumption is wrong.

Bart-Jan: No, correct. We started with a service, then moved to software, and now we blend them together. Right now we are a managed service with software and an agentic layer in the back that scales our service. We’re the biggest believers in AI native services. Because we built the software and the whole backend, we can give people the quality of a service offering with the speed of software.

Gil: That’s very interesting. Talk to me about some of the first use cases. You mentioned that in the very early days, you had some hunches that more eyeballs would lead to ranking higher. What were some of the early insights that told you this was worth chasing, and how did that lead to other pivots or revelations about where to spend more time in your business? You gave the example of not just driving your prices to the ground to get ranked first. What were some of those learning experiences in the early days?

Bart-Jan: We started experimenting in a lot of different directions. One of the earliest experiments we did was on Booking.com with a partner program called Preferred Partner and Preferred Partner Plus, which was big and is still big on Booking.com. We asked, if we enroll in a partner program with a higher commission but increase our rates, does it have a net positive impact?

In the tests we ran three years ago, it had a positive impact. That’s when we realized we were buying more eyeballs with a higher commission rate, but charging a higher rate could compensate for it. That was one of the early signals. Our potential guests are lazy.

They don’t want to scroll through every property. They do one query, and from that one query, they book. We then saw that booking behavior changes. The bigger the home and the longer the trip, the different the journey. But especially in our early days with hotels, where we had a lot of last minute short stays, the booking journey was super short.

Guests made one query with all their parameters, and then they booked. The properties ranked very high received the booking. Because of that early experiment with the commission programs, offset by rate, we saw that visibility and eyeballs really are buying more bookings.

Gil: That’s interesting that you found a difference with larger homes having a different booking journey versus smaller homes that may be more last minute. What does that mean when you talk about optimizing the listing? What do you do with that information once you have that hypothesis?

Bart-Jan: I think you touch on a very good concept there, hypothesis. We always start with a hypothesis. This is what we think could benefit this listing. Every listing is different and every market is different, and we’re lucky as a company that we manage over 25,000 units today, so we know what works in one market that we could copy in another.

But it all starts with a hypothesis, and then it’s about testing. Maybe this listing doesn’t work the same as the listing next door, because from the moment a listing is live in search, its digital identity inside those OTA searches is created. Every listing gets a different review score, different guests, and different cancellations.

From the moment it launches, you get completely different behavior. Because it depends on so many variables, and those variables are shaped by guests who are by definition unique, the listing creates its own identity and needs its own plan for optimization.

A listing could get families for its first three bookings, and an OTA may then show it higher in family categories when someone searches with a family profile. You can make a hypothesis, but the reality is often different, just because the digital identity can transform.

Gil: It’s an interesting concept because you’re not talking about a specific OTA. You’re talking about multiple OTAs you have to optimize for. How do you help property managers understand their differences in how they rank on different OTAs, and what are some of the things you’ve seen that are in stark contrast between one OTA and another?

Bart-Jan: When we look at OTAs, there are two types. You have Booking.com and Expedia, which were essentially built for hotels and are now moving a bit into short term rentals. Then you have Airbnb and Vrbo, which were initially built for vacation rentals. Airbnb and Vrbo are content OTAs where you can put content, and it’s all about telling a story.

You want guests wondering about their next trip. Booking.com and Expedia are more static.

They’re built differently. Expedia’s and Booking.com’s ranking algorithms are built around which listing will make Booking.com or Expedia the most money. Airbnb’s algorithm is built around which listing will match best with the guest so it leads to the best review score. That’s an essentially different way of looking at ranking.

Vrbo started a bit like Expedia, then moved a bit toward Airbnb, so it’s a blend. Airbnb and Vrbo are content OTAs. You can add a lot of pictures, titles, descriptions, and written information to sell and tell the story to a potential guest. Booking.com and Expedia are more static.

You upload the list of amenities, they show it, and they determine how your content is delivered. So optimizing the four OTAs is a different game. On Airbnb, it’s all about making sure the content and settings you choose will convince a guest to stay, which increases your conversion rate, then your bookings and your reviews, and then your flywheel starts.

On Booking.com and Expedia, you can get a lot done by just paying more commission. Those are some of the core principles that make them inherently different. What’s interesting is that Booking.com was always the biggest and strongest with discounts, Expedia also rolled out discounts, and now Airbnb and Vrbo are following with discounts.

So a lot of these OTAs are moving toward each other. A couple of years ago they were very far apart, but now they’re getting closer and closer, adopting the best features of each.

Gil: I’ve even seen Airbnb recently play around with commission types on both sides. There’s a rumor going around about what they call a direct booking link. I would argue it’s not direct, but it’s a link you can share that gives you around a 6% commission rate rather than the typical 13.5%. They also have one where you can promote yourself and favor them on the platform, or even take yourself off Vrbo and other OTAs and be exclusive to them. Have you seen any of these changes actually move the needle on bookings?

Bart-Jan: I think what Airbnb is doing is interesting. It’s essentially what Booking.com and Expedia have enabled for ages, and now everyone is asking why Airbnb is doing this. The other OTAs have been doing it already, just less publicly. You have to apply to get those special links.

You can import Booking.com stock into your own property listing, and you can even earn kickbacks on those things. But your point about only enabling one OTA is an interesting one. Larger property managers are usually on three or four OTAs, while in the States, in a lot of areas, Airbnb is the dominant one.

What we see is that listings with a split distribution mix, say 50% of bookings from Airbnb and 50% from Vrbo, are actually not the best fit for ranking performance, because Airbnb bookings block 50% of the calendar on Vrbo, and Vrbo bookings block 50% on Airbnb. You’re limiting the availability and stock you provide to both platforms.

The same analogy goes for owner stays. If an owner stays for a month, that’s actually very bad for Airbnb rankings. It’s better to set the price at 10K per night so the owner can still stay, rather than having a booking block the calendar. But then the argument could be, why not just go with one OTA?

Then you have a huge risk. If a listing gets suspended for some reason, you risk the whole business. So a property manager always has to find the balance: where do we push for single channel dependency, and where do we want multichannel coverage to lower risk?

It’s always about finding the right balance.

Gil: That’s super interesting, that they would penalize you if you aren’t exclusive to them and bookings happen outside of the platform. How much of a swing have you seen that make in ranking?

Bart-Jan: We generally see that hosts, mostly smaller hosts, are always higher up in search, and those are also the hosts who are exclusively on Airbnb. But it’s not fair to conclude that it’s because they’re exclusive to Airbnb. The difference we see between a host and a property manager is the amount of care they have for a property.

They’re the type of people who describe every detail, where you can even find which shampoo brand or coffee maker you’ll see in the property. So the biggest difference between hosts and property managers is the level of detail, because they know their home.

It’s mainly their own home. They’re super passionate, they welcome every guest, so they get very good review scores. They pour their heart and soul into the listing. So it’s unfair to say that listings exclusive to Airbnb are by definition ranked higher. We do see a positive trend, but it’s mainly hosts, who are single channel dependent and have high review scores.

Gil: It’s almost like correlation, not causation.

Bart-Jan: Correct.

Gil: I’m starting to pick up that a lot of different variables come into play, and you talked about a few of them: descriptions, reviews, pictures, pricing, perhaps even length of stay. Two part question. First, are there variables outside of these that people should be thinking about optimizing? And second, if you were to rank the most important ones, what are the top three things you need to nail if you’re trying to optimize for rankings on an OTA?

Bart-Jan: Bookings, reviews, and consistency. A lot of people will claim the title and summary are the most important things. Those are important, but for conversion reasons. If you have a bad description or bad titles, your conversion may drop, which won’t lead to a booking, which won’t lead to a review, and it starts to spiral down.

But the most important thing for the search algorithm of Airbnb and any other OTA is simply receiving a booking. Receiving a booking, receiving a review, preferably a five star review, and then keep going from there. To cluster the first two elements, booking pace is one of the most underrated things for the algorithm. We’ve seen property managers with a listing that sells out its whole inventory immediately, and they’re happy because they have a full calendar.

But that’s actually detrimental, because it means they’re no longer selling consistently. Their full calendar is blocked, Airbnb isn’t indexing them, and when their calendar opens again, they have to restart everything. So booking pace is probably the most important thing, along with getting reviews.

Title, description, and pictures are all important, but for conversion purposes. If you’re getting eyeballs on the listing because you’re seen, and your pictures are well organized, and your description and title are there, your conversion will be good. And because your conversion is good, you’ll get a booking.

That booking leads to a review, which is the flywheel. So listing optimization, visual and content optimization, are important, but they’re accelerators. They’re not what starts the flywheel of being ranked high or low.

Gil: That’s interesting. I would have thought pricing would be one of the most important factors to look at.

Bart-Jan: Yes, of course. To your point, maybe it’s the most important one, because pricing also impacts conversion, bookings, and so on. If you have a perfect listing but you outprice your market, you won’t get booked, and vice versa. What I’m trying to say is that OTA optimization is a unique game of balancing all the different factors. When you read people online saying, “Do this on your listing and you’ll get more bookings,” in the majority of cases it’s not true, because it’s such a unique art of balancing booking pace with price, with reviews, and with how you react as a property manager when a bad review happens.

Every property manager or host will get a bad review at some point in their hosting career. The most important thing is how you react to that bad review in pricing, in your review response, and in how your listing is formatted. If guests complained about construction work in the street, mentioning that the construction is over is super important for Airbnb to highlight you again.

So in a lot of cases, the response is as important as the review itself.

Gil: That’s interesting. There are rumors that Airbnb, and possibly some of the other OTAs, look at messaging and use it to figure out whether you’re delivering on that perfect stay. Do you see that as true in any of your data?

Bart-Jan: What we generally see is that the speed of answering messages is super important. Especially with the wave of AI chatbots and AI messaging tools in short term rentals, that’s very beneficial for a lot of property managers and hosts using them. Response rates are super important. We haven’t seen much evidence that the messages themselves are being used.

Of course, there are the classic cases where, if you ask a guest in a message thread to book directly, that gets flagged, but we haven’t seen evidence of what you were suggesting.

Gil: I think there’s some suspicion that a guest may leave you a positive five star review but note something about cleanliness on the day of check in, and whether that outreach actually makes an impact. But it sounds like it’s inconclusive. There’s not enough data to say whether it has a negative or positive impact on your overall performance.

Talk to me a little bit about the shift in AI and what that means for you and your clients. When you first started this company back in 2023, that was the rise of ChatGPT, but it was less embedded in our systems than it is today.

Not a lot of apps back then embedded AI natively into their platforms. Now AI is everywhere, both in what property managers use day to day and in the tools we build for them. Anything involving algorithms, crunching large datasets, finding anomalies and discrepancies, and optimizing is one of the best use cases for AI. So on your side, what has that unlocked for you and your clients over the last two years?

Bart-Jan: Our positioning in the market today is an AI native revenue management service, where we live inside the channels our clients’ teams communicate in, whether that’s Slack, WhatsApp, or something else. Usually that’s an account manager, supported by AI on the other side, to make sure answers to their questions come quickly.

Because to your point, Gil, AI is everywhere, and people adapt to using it. People are very used to instant answers. When they want a piece of information, they want it within seconds. That taught us that every piece of information our customers ask for, we should be able to provide very quickly, or at least flag that we’re working on it.

That’s probably the most visible application in our whole customer journey today. When someone is in Slack with us and says, “Owner ABC is concerned about their rental rates for the rest of next year,” they get an instant answer. But for product building, this has unlocked a lot, because we work with huge piles of data: ranking data, revenue data, on the books data, click ratios, all those kinds of things.

With AI, it’s so much faster to find what’s working where and what isn’t. In the past, we had a lot of people working through those big piles of data, and now it can all be scaled. Based on the data analysis, some things we know we have to do, so those are deterministic, but in a lot of cases AI can spot a trend that can then be applied on an OTA.

So the time between spotting and executing has been dramatically shortened.

Gil: That’s super interesting. It’s almost as if AI becomes your full time researcher that’s always there. It goes into much greater depth and can go through large amounts of data. It lets you, as a human, form hypotheses, test them across large datasets, and then tweak your internal algorithms to reflect that and see whether it closes the loop.

That’s the sense I get of what’s happening behind the scenes.

Bart-Jan: Correct. A lot of people have written their opinions on AI, but generally it’s amazing what it can do.

Gil: On that point, where do you see things going for AI and for you, and how do you want to leverage AI even more effectively in the future?

Bart-Jan: Essentially, we’re building a big data model on which actions on which OTA have an impact on revenue performance, where, and how. AI is increasing the speed at which we can draw conclusions, strengthening the execution layer, and expanding the actions the software or agents can take.

For the future, we see the possibilities of AI only growing, where humans are given superpowers and one person can do the work of maybe two people today. A lot will change for us as a company, but also for our customers. They’ll get results even faster, because the faster we can detect trends and act on them on an OTA, the faster our customers see the impact.

Gil: If I unpack that a little bit, there are three layers to it. There’s the learning layer, learning about the datasets. Then there’s the execution layer, actually making the changes. And then there’s an evaluation layer.

That’s the cycle it goes through. The tighter you can close that loop, the faster you can learn, differentiate, and identify which changes will actually create impact.

Bart-Jan: Exactly. That’s the beauty of it: trend detection and execution speed.

Gil: Do you see the OTAs looking at you as a potential threat or as something they want to support? Where do you see yourself in terms of being frenemies with the OTAs? In a lot of ways, you’re reverse engineering what they’re doing, but you’re also helping their property managers get what they need out of it.

Bart-Jan: We generally have very good connections and collaborations with all the different OTAs, because what we’re doing is maximizing bookings on their channels, which also means more commission for them, which is why they’re happy. We’ve also discussed with the OTAs that the level of support they need to give our customers is fairly limited, because we solve the whole puzzle.

We make sure that whatever is needed on an OTA is optimized, with the end goal and target variable of making more revenue. Making more revenue means either selling more or selling the same stock at higher prices, and at the end of the day the OTAs take their cut, so they win.

Gil: Before the show, we were talking a little bit about how AI is changing search in general. I want to touch on that. What are you seeing in terms of consumer behavior now that folks are using ChatGPT, Perplexity, and other AI search tools?

How is that changing your world?

Bart-Jan: The way I look at it is what I said earlier. People are used to instant dopamine: “I want to know this now, and I will know it now.” There’s a very short cycle between question and answer, and that has translated into every part of society, where people are used to getting what they want right away.

The same will go for travel. We have seen after COVID that the guest journey, from opening your first search to booking, has become shorter and shorter. In every Booking.com, Expedia, and Airbnb report, year over year, they’re reporting shorter cycles between search and booking. Of course, this is not true for all verticals.

For bigger homes and bigger families, that’s sometimes different, but in general, that’s the trend. Which is where different OTAs, and I assume all OTAs, will move into conversational search, where you will be able to go to Booking.com or Airbnb and type, “Hey, I want a two bedroom home in Orlando,” and that will be the query.

So the way of searching is about to change. It’s about to mimic conversational tools like Perplexity, OpenAI, Claude, and others. The OTAs will mimic that. What we’ve found from tests we ran with people from Booking.com, who are already experimenting with this, and people at Airbnb, is that it’s all about making sure your listings are in sync.

What I mean by listings being in sync is making sure your listings don’t have any factual inconsistencies. If you mention somewhere in your listing that you allow pets, but the house rules you copied from another listing say you don’t, that’s a factual inconsistency.

When an LLM populates listings to show potential guests, it will spot that these things contradict each other. It isn’t sure, so it won’t show that listing. So with search going conversational in the future, accuracy, completeness, and sync are going to be the most decisive factors.

Gil: That’s interesting, because we see something similar on the direct booking side. As LLMs pull and scrape content from websites, we’re moving toward much more structured data. Most vacation rental websites are now expected to have strong vacation rental schemas for every single property, so that when they show up on your homepage, it’s very structured.

It sounds like the same thing is happening on the OTA side, and you’ve probably seen this already. Over the last six months, if you go inside the Airbnb app, they’ve asked, “Do these amenities exist in your property? We’re finding them in your descriptions.”

As they mature their first party primitives, like the actual property amenities, they’re trying to normalize everything so they’re ready for more conversational search. That’s what I think we’re both seeing.

Bart-Jan: Yes, correct. And it makes sense on both the direct side and the OTA side. It’s how people are trained and how their behavior has changed since ChatGPT launched a couple of years ago and became mainstream. People are adapting their behavior, and OTAs and direct channels have to adapt. So as a property manager or host, it’s about making sure you’re not leaving anything behind and getting on that wagon soon enough.

On an OTA, it’s about starting as soon as possible, because if you only fix the inaccuracies three or four months into being live in conversational search, you’ll need a period of time to get kickstarted again. And I assume, Gil, but you’ll know this better than me, that the same goes for direct channels.

It’s not a one day fix you can implement.

Gil: No, and if anything, these LLMs take a long while to retrain and recrawl websites. I think property managers who have been investing in this for the last six months, if not longer, are probably in the best position, because it does take time. It depends on the model too. Claude takes especially long, but Perplexity and Gemini are rather quick at scraping and pulling live data. All to say, this hygiene work is necessary to focus on now if you want to take advantage of where things are moving.

Bart-Jan: Yes. We have run a lot of analyses on properties live on different OTAs, and the same thesis applies to direct channels. The number of mistakes live in listings is crazy. We started looking into why there are so many mistakes in listings.

Sometimes you open a listing and it says two bedrooms, and then in the next section it says three bedrooms, which for LLMs is killing. It kills the ability to show up in search. Our hypothesis is that as a property manager grows, the work becomes part of an SOP here and there, and so many people are involved in creating a listing.

So many people are involved in crafting a listing, and there’s no proper QA layer inside the SOPs anymore. A QA SOP will become very important in the future.

Gil: Awesome. Bart, I wanted to talk a little bit about the direct booking side. I know you focus intently on optimizing for OTAs, but I’m interested in hearing from you on the counterbalance. If folks are trying to balance their independence through direct bookings, what tips have you seen or would you provide?

Bart-Jan: We generally see that people who work on OTA optimization get a spillover to direct as well. But there’s a very important one, and we’ve seen successful stories of property managers and hosts doing this: using the OTAs as a way for guests to find the listing, knowing that some guests will copy and paste the listing and go to the direct channel.

When we looked at it ourselves, the majority of listings are unmatched. If you copy and paste the exact Airbnb title, you will never find the direct channel. So my biggest advice is to work on SEO for your listing title, something a potential guest could copy and paste into Google, because that’s their exact behavior.

They copy the Airbnb title and paste it into Google. If they can’t find you, you have an SEO problem. We’ve also seen positive impact from people running ads on their own listing title, because the only people clicking that ad are coming from an OTA and heading to your direct channel.

And of course, there are other successful cases where I’ve seen people create agents that scrape competitor listing titles and then match them. All of that is possible, but I think the basics are making sure that if someone wants to get off an OTA, you can be found.

Gil: Yes. I think how you name your property is a pretty important part. I made a mistake in the very beginning by using a very generic name for our property. Anyone who invests heavily in direct gives every property a unique name, because that’s a seed you can leave on the OTAs for someone to find you again.

If you don’t have any identifier for them to find you, it’s going to be extremely hard. The ads idea you mentioned is quite a nifty trick, because like you said, it won’t cost you anything if no one clicks. But if someone searches specifically for the key term you use, even if it isn’t your listing title, it leads them back to you.

So it’s a very cost efficient way to make sure you’re found, even if you haven’t optimized for SEO. On our side, we have some pretty mature property managers who want to optimize what we call the meta descriptions and meta titles. Typically on a webpage, you have a summary that’s pulled from the content.

In our case, we usually pull the short description as the meta description. But folks who are really interested in optimizing their direct listings can override that, and sometimes they seed that information with what they have on the OTAs so they can be found.

So it’s about thinking through what the guest journey looks like, how people move through it, and where they’re finding you. Some people do really well by optimizing the OTA to direct migration, while others lean on more traditional marketing tactics.

Whatever it is, really think about the entire guest journey and make sure guests can find you if they want to find you.

Bart-Jan: Yes, correct.

Gil: Awesome. Bart, we usually end the show with three questions, so I’ll ask the first one. What’s a book you’ve read that has inspired your life or your career?

Bart-Jan: You asked me to prepare this question, and I have to be very honest. I don’t read a lot of books.

Gil: That’s fair.

Bart-Jan: So I would say there’s a book on the Entrepreneurial Operating System. It’s one of the books I have read.

Gil: Is that EOS?

Bart-Jan: Exactly, EOS. It was recommended to me by a property manager, actually, and it changed how I look at goal setting in companies and how I look at momentum.

So that’s probably the one, but in all transparency, it’s probably one of the five books I have ever read in my life.

Gil: That’s so real. And I suspect that right now, as a founder, you have less time to read than usual.

Bart-Jan: And then you think you should be reading, but in reality you’re never reading.

Gil: For our second question, I think this one is very fitting for you. What’s one piece of mindset advice you would give to someone starting something completely new?

Bart-Jan: Just do it. You can think as much as you want, but you’ll never know if you don’t just do it. If you have an idea, whether you’re super convinced or not, go and test it. Test it small and see if it works. If it doesn’t work, at least you tried it. Otherwise, you’ll spend years thinking, “If only I had started that business.”

So I would just say do it. You cannot lose anything.

Gil: And the last question. For anyone looking to get started in direct bookings or amplify their direct bookings, what’s one tactical takeaway you’d want them to put into practice this afternoon?

Bart-Jan: Start by making your direct channel’s offering more appealing than the OTAs’. Offer early check in for everyone who books direct, complimentary breakfast, free cancellation up to a certain number of days, or a free welcome basket. Something that moves the needle on why people would move away from the OTA convenience.

At the end of the day, what an OTA offers is convenience, and that has to be matched in your offering. It’s about finding something that works in your local market. If you’re close to Disney, maybe it’s a discount code for the Disney parks, that kind of thing.

Gil: I would stress that last part. It could be any of these things, but it starts with understanding who your ideal guest is, who you’re trying to attract to your properties, and what they care about. If someone is planning a trip and worried about cancellations, especially young families, that’s a real concern because things come up at the last minute, so cancellation is a big factor. For other travelers, early check in may matter more. So it’s really about understanding who your guest is and what carrots would actually move them.

Bart-Jan: Yes, correct. And we’ve seen the greatest success with that.

Gil: Awesome. Bart, it was a huge pleasure having you on the show. For folks who want to get in touch with you, where can they find you?

Bart-Jan: They can look me up on LinkedIn and send me a connection, or go to our website, otamiser.com.

Gil: Awesome. Bart, it was a huge pleasure. Well done growing the company to what it is, really digging deep, and figuring out how to help your clients optimize their rankings across multiple variables.

Bart-Jan: Thank you very much, and looking forward to seeing you at VRMA.

Gil: Yes, I’ll see you soon. Bye.

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