Direct Booking Conversion: Why Traffic Alone Won’t Fill Your Calendar with Amber Knight

Summary and Highlights

👤 About Amber Knight

Amber Knight is the General Manager at BookingsCloud, a performance marketing company that helps vacation rental managers turn traveler demand into direct bookings. Drawing on her roots in a century-old media company called Advance and years of experience applying data-driven ad technology in the automotive sector, Amber has spent the past two years adapting that infrastructure specifically for the short-term rental space.

At BookingsCloud, her team connects directly to a manager’s PMS, builds fully automated, inventory-specific ad campaigns through Meta, and uses an opportunity scoring system to prioritize which properties get ad spend based on revenue potential — not gut instinct. The result is a system that has delivered return on ad spend as high as 100X for established operators.

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🔑 What You’ll Take Away From This Episode

Before getting into the highlights, here’s the core thread running through everything Amber shares: direct booking conversion doesn’t fail because of bad marketing — it fails because the traffic and the website aren’t working together. Ads bring people in. The website either closes them or loses them to an OTA. Once you understand that, everything changes.

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📊 Why Data-Driven Ads Work Differently in This Space

Most property managers who run ads are either boosting social posts or running brand-level campaigns that send traffic to their homepage. Amber explains why that approach leaves a lot on the table.

BookingsCloud operates differently. Rather than building audience segments manually or targeting by demographics, they feed Meta a rich stream of property-level data — amenities, pricing, photos, descriptions — and let Meta’s machine learning figure out exactly who to put each ad in front of. Every ad is inventory-specific. Every click lands directly on the relevant property detail page, not the homepage.

The analogy Amber uses is the automotive industry: if you want a white Toyota 4Runner with a specific trim package and you see an ad for exactly that vehicle at a dealership five miles away, you’re going to click. That same logic applies to vacation rentals. When a guest sees an ad for a property that has the hot tub, the pet policy, the neighborhood, and the nightly rate they’ve been searching for, they’re not settling — and they’re far less likely to get distracted by price.

This is a meaningful shift from how most operators think about social advertising. And the data backs it up.

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🎯 The Opportunity Score: Spending Where It Actually Matters

One of the most practical frameworks Amber introduces is what BookingsCloud calls the opportunity score — a data model that determines which properties in a portfolio should receive ad spend in any given month based on their booking window, revenue potential, and current occupancy.

Think about what that solves. A $1,000/night property with one open week and a $300/night property with three open weeks have very different revenue profiles. Experienced managers make these calls intuitively. BookingsCloud makes them systematically, across an entire portfolio, using a data science team.

The result is that operators stop spreading ad dollars thin across everything and start concentrating spend where it generates the most return. It’s not about filling last-minute gaps — it’s about applying pressure at exactly the right moment in the booking window for the right property.

If you want to understand how scalable direct booking strategies connect to smart ad spend, this section of the conversation is essential listening.

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🏠 Why Guests Who Click on Your Ad Still Book on Airbnb

This is the part of the episode that will make a lot of operators uncomfortable — and it’s the most important thing Amber says.

When BookingsCloud sends guests directly to a property detail page, 20 to 40% of them still end up booking on Airbnb or VRBO. Not because the property isn’t right for them. Because they don’t trust the website.

They found the property. They want to book it. But they trust Airbnb to handle things if something goes wrong. That trust advantage — built over years of OTA use — doesn’t go away just because you have a beautiful website.

Amber breaks down what actually builds trust on a property page: authentic reviews (including the occasional less-than-perfect one with a thoughtful response), clear evidence that a real person is reachable, and a booking flow that feels familiar. Guests aren’t looking for novelty in how they book — they want the process to feel like something they’ve done before. The moment it feels unfamiliar, conversion drops.

Gil adds something equally important from the CraftedStays side: when the booking flow redirects to a PMS engine on a different subdomain, the URL change alone signals to guests that something is off. Consistent domain, consistent session, consistent trust. Building trust on your direct booking site isn’t optional — it’s the difference between capturing a booking and handing it to an OTA.

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⚡ The Property Page Has to Do More Work Than You Think

When traffic goes directly to a property detail page instead of the homepage, the rules change. Most operators build their homepage to carry the trust load — host bio, FAQ, about section, social proof. But if a guest lands on a property page first, that page has to do all of that work on its own in about 10 to 15 seconds.

Amber’s framework for what a guest needs to feel in those first seconds:

Is this the property I’m looking for? Does it match the amenities, the location, the price, and the vibe I’ve been searching for?

Do I trust this? Are the reviews real? Does the description match the photos? Is there someone I can reach if something goes wrong?

A guest who gets a “yes” to both will keep moving. A guest who gets a “maybe” will close the tab and go to Airbnb. The property page is the new homepage for a large percentage of your paid traffic — design it accordingly. Understanding what converts on a direct booking site matters more than ever when ads are driving cold traffic straight to the property level.

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🤔 Build vs. Buy: The Croissant Question

One of the most memorable moments in this episode is Amber’s croissant analogy. Making croissants from scratch takes three days. You can do it — but you can also walk down the street and buy one for three dollars. And that’s assuming you already know what you’re doing.

The point applies directly to how operators think about their websites, their ads, and their marketing infrastructure. As AI tools make it easier than ever to build things yourself, it becomes tempting to try to build everything. But building something mediocre in an area where professionals obsess over the details every single day doesn’t serve your business — it just keeps you busy.

Gil and Amber both make the case for knowing where your time compounds. Cleaning, ops, guest communication, marketing, website conversion — these are all areas where subject matter experts have years of iteration and data behind their recommendations. The operators who grow fastest are the ones who know when to bring in that expertise rather than trying to absorb it all. This also connects directly to how the Billboard Effect works in your favor once you have the right infrastructure in place.

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🧪 The 100X Case Study — and What It Actually Proves

Amber shares two client stories that illustrate the full range of what’s possible with data-driven ads.

The first is an established operator in the Outer Banks — a company with decades of history, a recognizable brand, properties on the best beaches, and 70% direct bookings before BookingsCloud ever came in. For them, the trust problem doesn’t really exist. Guests already know who they are. They go every year. When the ads show up on social media, it’s not an introduction — it’s a reminder. Their return on ad spend hit 100X. One dollar in, a hundred dollars in bookings.

The second is a manager spread across six markets with no more than 15 properties in each, no defined brand identity, and a self-built website. The ads drive traffic. Guests arrive. The conversion rate is a fraction of what it could be. Not because the properties are bad — because the guest has no reason to trust the brand, the website doesn’t feel authoritative, and the checkout experience is inconsistent.

The delta between these two operators isn’t the ad system. It’s the foundation the ads are driving traffic to.

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📬 Reviews Are Revenue

Amber is direct about this: reviews are not a nice-to-have. They’re a financial asset.

Two identical properties — same location, same amenities, same pricing. One has no reviews. One has twenty. The one with reviews will generate $15,000 to $20,000 more in revenue over the course of a year. That gap only grows as review count climbs.

And it’s not just about volume. Authenticity matters. A page full of five-star reviews starts to feel curated. A review that mentions the rain, paired with a thoughtful response from the manager, signals to guests that the reviews are real and that someone is paying attention. That’s 90% of trust right there. Pairing strong reviews with consistent content creates a trust loop that compounds over time.

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🔄 Channel Diversification: What 2025 Made Clear

Gil brings up something every operator in the space felt this year: Airbnb made several platform changes in 2025 that pulled leverage away from hosts. Review distribution, visibility mechanics, pricing pressure — the platform is harder to work with than it used to be.

Amber’s response is straightforward: businesses that concentrate more than 50% of their revenue on a single distribution channel are exposed. The ones building toward sustainable independence are diversifying — not abandoning OTAs, but making sure they’re not at the mercy of any one of them. Vacation rental marketing that supports long-term direct booking growth starts with understanding where your revenue actually comes from.

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⚡ Rapid Fire with Amber Knight

📚 Book recommendation? Supercommunicators — a book about how to communicate effectively across people with completely different thinking styles. Amber is currently using it to bridge the gap between revenue managers and marketers, who often speak entirely different languages and need a translator to work well together.

🧠 One piece of mindset advice for someone starting something new? Your 100% is probably overdoing it. Learn to operate at 70% — because the gap between where you are and where you want to be is a superpower, not a problem. The people who stop at adequate are the ones who can’t see the gap. Seeing it is what keeps you improving.

🎯 One tactical thing anyone can do this afternoon to improve direct bookings? Walk your own checkout process from start to finish — from finding the property to receiving the third guest email. Do it as a guest, not as an operator. Then have someone else do it. Then have someone who is not tech-savvy do it. You will find 15 things to fix, and most of them won’t cost you anything. And get your reviews working for you — the first ten reviews on every property are critical. They are not a formality.

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🤝 Connect With Amber Knight

🔗 LinkedIn: Amber Knight 📘 Facebook: BookingsCloud 📸 Instagram: @bookingscloud

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🚀 Ready to Turn Your Traffic Into Bookings?

Everything Amber described — the property page that has to earn trust in 10 seconds, the checkout that can’t redirect to a different domain, the booking flow that has to feel familiar — that’s exactly what CraftedStays was built to deliver.

If your traffic is there but your direct bookings aren’t moving, the problem isn’t awareness. It’s conversion. And conversion starts with the right platform.

👉 Start your free trial at CraftedStays.co and build the direct booking website your marketing deserves — no agency, no code, no waiting.

Your guests are already searching. Make sure your website is ready to close.

Transcription

Gil: Before we bring on our guest, I wanted to talk just a little bit about something that I’ve been hearing a lot from hosts. I keep on 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’re having 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, and you can keep on testing and improving as you learn. You can 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 ahead and 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 on top operators to discuss hospitality, operations, and marketing.

On today’s show, I have Amber Knight from Booking Clouds. She runs one of the most sophisticated ad systems in the space, and today, we break down how she approaches ads differently and how she’s seen as much as 100X return on ad spend with some of our top clients. So without further ado, let’s bring her in 

Gil : Hey, Amber, welcome to the show

Amber : Hi. Thank you. Great to be here, Gil

Gil : Yeah, it’s been a long while. I, I missed some of the more recent conference circuits, but I remember meeting you, I think– I don’t know, was it Burma of last year? Or maybe even o- other, another conference there. But it was… No, it was, um, VR Nation, I think it was, when I originally met you

Amber : Mm-hmm. Yeah, last year.

Gil : Yeah. And you guys have been moving a lot.

You have been growing quite a bit. Maybe to kick us off, Amber, do you mind giving folks introduction on who you are and what you do?

Amber : Yeah, absolutely. Um, so I’m Amber Knight, um, and I am launching Bookings Cloud, and we help vacation rental managers turn traveler demand into d- d- direct bookings by matching what guests are searching for, um, with the properties that are ready to book, and sending that traffic of those qualified tra- travelers directly to, uh, the property detail page on their website

Gil : Yeah. And you folks are very different, at least from what I observed, than your traditional ads company. You guys are extremely tech-heavy. Talk to me a little bit… And, and a lot of outside industry knowledge as well too. Um, talk to me a little bit about kind of the origins and where BookingsCal came from.

Amber : Yeah. Um, so we are, we firmly believe that, um, data should be applied to marketing decisions, right? And this is not, um, a standard, I’m gonna say always in the vacation rental space. So really our history is, um, you know, we, we are kind of coming out of the foundations of a, a 100-year-old private media company called Advance, and they’ve been in newspapers and analog and like, how do you apply data to marketing decisions to advertising, right?

All the way through. And so really kind of being on the front lines of innovating from going from analog to digital, um, and especially in the automotive side, right? So those ads that you get in front of you when you’ve already late in the stage of deciding what kind of vehicle you want, that you want a white 4Runner with a special package, and then you get an ad in front of you on, in digital marketing that is that p- that vehicle, um, with the package you want that’s five miles away.

You click on that ad, you’re like, “Okay, I’m gonna go to that dealership and I’m gonna test drive this car.” That ad and the automation of that ad, and the automation of putting that ad in the right place requires a ton of data, right? And it also is like there’s a lot of like work to create that many ads, right?

So how do you do that and how do you automate some of that and how do you focus that? And so that technology from automotive, we’ve kind of spent two years adapting specifically for the short-term rental place, space. So if you look at that, you have inventory, these properties that need bookings, right?

So we will, we use a thing called an opportunity score to prioritize these, these properties that would benefit the most from additional visibility of eyeballs on these properties. And we put those ads in front of people who are looking for properties that look like, that look like the properties in that, in that portfolio, and send them to the website.

So it’s basically using social media to send, to get ads in front of people where they are, send a ton of qualified people who are looking for properties that look like yours to your website, right? Um, now that website still has con- has to convert, which is, uh, you know, you’re an expert in. And so we work through that, but that’s, that’s really what we do at the end of the day of what would, what do you do if 1,000 or 5,000 or 10,000 more people are qu- looking for properties that look like yours and they’re on your website?

Gil : Yeah. So, yeah, so you’re almost thinking about like, ads, I think a lot of folks, they think that, “Oh, I magically get some ad served in front of me,” and sometimes that’s true, but there’s actually a lot of mechanics that goes behind it. And I think the orchestration behind it is, it can be done simply, but it also can be done very complexly, where you’re actually hitting the target much more on the bullseye, and you’re being a lot more strategic about that.

And I think the… As you’re kinda explaining what BookingCloud does, I almost think of, like, how you guys run ads is more like a pipeline, where there are a lot of inputs. You have some signal that someone’s interested in something, and you’re looking and you’re getting more and more data about that one, and you’re trying to figure out what is the right ad to put in front of that person to get them to click on that.

Um, because that’s ultimately the goal, is to get them to click, and then hopefully they land somewhere that they wanna click further and actually do a purchase or do a booking there. So I almost think of it as, like, a pipeline. Do you see it the same way, or do you see it some other analogy?

Amber : Um, I think Meta is the pipeline, right? So Meta knows what do I need to put in front of somebody to, to get them to interact with this ad, right? And so what we’ve done is we’ve gone to Meta and said, “Hey, what do you need from us to get people to get the ad, right ad in front of the right person?” And they’re like, “We need all this,” like basically a lot of property detail data.

So we connect to your PMS, we pull those property amenity details, we pull the listing prices, right? So that we get the right photo, dynamic photos, so photo of a pool for the person looking for a pool, the right amenities, so we’re serving the right amenities to somebody looking for that, those amenities.

The pricing, so we’re putting a $5,000 a night property in front of somebody who’s looking to pay $5,000 a night, right? Um, and then really kind of like we’re, we’re, uh, tagging those photos so that Meta can read them better, so that they can pick the right photo. We’re pulling the data in there so that the description, you know, we’ve got a special like specific LLM just for what’s the right way to convert all of the amenity details and the listing details into the right like two lines on an ad to get the clicks that will direct, like convert to not just views, but a booking, right?

So we really wanna connect all of this to revenue, and that’s, it’s a whole proc- there’s a ton of data involved. I got way more in the weeds than I expected to. But yeah, Meta knows what they need, right? And so the question is like, how do we give Meta what it needs and then give it a feedback loop of like, “Here’s who actually booked this property, and send me more people like this who wanna book properties that look like mine.”

So that you can, like we’re functionally training Meta on your website and on your portfolio and giving them a ton of data to do, and it would be like, I’m gonna say, uh, not cost-effective to do it manually. So we, everything’s automated.

Gil : Yeah, that’s what, that’s what I was gonna ask is like, there’s… I mean, if you have like two or three properties, you might be able to manually create an ad for them. But if you’re– And maybe that’s not even true. Like, I’m interested in hearing like one property, how many different ads are being shown or being created that’s being fed back into, to Meta.

My, my guess is not, you’re not just creating one ad per property, you’re creating a ton of ads per property, and you’re then trying to then target individual, your, your segmentations according to that. Is that right? Or

Amber : Yes. So we’re, again, we’re not trying to segment or build a customer audience or anything. Meta’s doing that already, right? And they can tell us who interacted with our ads, but like we’re, we’re saying t- give us everybody. ‘Cause it doesn’t, it doesn’t build into the like once th- you know, somebody who’s building, planning a trip that they’re coming to once, right?

Those custom audiences only go so far, and they’re usually, they’re– it’s always lagging information, right? It’s never leading information. So we’re working through, through that process. Um, but it’s, yeah, it like, it, yeah, so we’re just, we’re essentially working with Meta to say like, “Let’s line this up.

Let’s make sure that you have everything you need and make that work.”

Gil : Yeah. Um, I think it’s, it’s very different than I think how… Like, even like for us, like in SaaS, for instance, we have ad sets and we have segmentations and we build a list and we have lookalike audiences. It sounds like you guys are using a very different way of approaching it, where you’re feeding Meta a bunch of different assets that they can run ads across.

You’re giving them some sort of feedback loop, maybe via like a conversion tracking, and then you’re telling them, “Okay, you sent this type of traffic before, it worked really well.” And you’re, you’re basically trying to give it as much data for them to figure out who sh- should, who should we target, and almost like do it dynamically fast enough where they’re in control, Meta’s in control of being able to run that.

Amber : 100%. So it, it’s, it, they are fully dynamic. Like there’s, I think there’s 12 different ad types, right? So we’re getting in front of, um, people where they are, and that’s really what you wanna do. So we’re getting… And social media is different, right? Because you’re getting in front of people, not necessarily when they have their credit card and they’re ready to book a $20,000 stay, um, but you’re getting in front of them at that late stage of booking, so they’ll come back, right?

And that’s kind of what we’re getting is like they’re scrolling late at night, they see the property, they click on it, great. They go send it to whoever’s gonna book, or they send it to themselves and they book it the next day. And so we see a lot of that behavior, but it’s, it’s getting in front of people where they are in the format that they’re looking at.

Gil : Yeah. Um, you mentioned you had originally come from kind of like the automotive industry. What’s kinda like the similarities that you’ve seen in the automotive industry versus in the vacation rental space? What, what, what is very similar and what’s like something that you’ve actually surprised to find like it’s actually very different in terms of, uh, maybe the booking flows or things you’ve learned along the way?

Amber : Yeah. Well, it’s, they’re both like high value assets, right? But it’s also kind of expiring because the, the, the vehicles on the lot are constantly changing. It’s not like there’s 20 of the same vehicle. They’re all like a little bit different, right? So you really wanna make sure, and they’ve done testing on this of like the aspirational pictures of like people camping with a Subaru or whatnot, versus showing the exact vehicle somebody’s looking for with the exact trim set, right?

So you’ve got this situation where 60% of, 67% of people who are looking for a vacation rental don’t find the vacation rental they’re actually looking for. They’re settling for something. What are they– They get overwhelmed, they pick the next thing, right? It’s not exactly what they’re looking for. So what if you can put exactly what they’re looking for, that’s a very specific targeted down to allows pets, what neighborhood, how much per night, does it have a hot tub kind of situation?

What if you can put that right property in front of the right person who’s looking for that? They’re gonna be willing to pay more because price then becomes less of the sticking factor, right? So you’re not leading with price, you’re leading with best fit, and that’s, that’s where all of us wanna be. And so then you’re talk- like that’s where you, where you go, and that is highly targeted, right?

And you’ve gotta use data to do that because the manual time that it takes is not worth the cost to the, the like paying somebody to go manually upload all this data to do this, manually creating the ad, and manually updating it and changing it as your inventory changes, right? So that’s kind of that big specific piece is that, that inventory is changing so much and the priority of the inventory and finding your highest and best use of your ad dollars to convert it into revenue and just that’s what counts.

Gil : and so when you’re talking about inventory, are you talking about, like in our space, in the vacation rental space, are you talking about specific stay dates that are available that you’re trying to fit in there? Or more so the, the overall property?

Amber : yeah. Medic does not look at specific stay dates, right? But you can– we can look and say at the beginning of a month, and like all of our clients are like in the middle of doing this right now, of, “Hey, we have… Here are the properties that are in their optimal booking window. Which properties, if I got more eyeballs on this property, would I get the most money if I got more bookings on these properties?”

Okay? So we prioritize those properties to say, “Here’s the ones that need extra visibility, and this is where you should spend your dollars this month to get more visibility in these properties, because people are likely to book them, and you’re gonna make the most money booking these properties versus these other ones.”

So, and that gets into like, again, like you’ve got to figure out, okay, you’ve got this property that is $1,000 a night, but it only has a week open. This property’s $300 a night, but it has three weeks open. Which one is more valuable if y- which one has more revenue potential, right? And so they’re kind of, but like you’re doing that through all your properties, and experienced managers do like manually figure that out, like intuitively, and we’re applying data to that to be able to…

We have a data science team, and so we try to like help you not have to think through that quite as much, and that allows you to just be like, “Okay,” like, “They’ve got it. Here’s– This is where BookingsCloud says to spend money.” That’s where you go, and you can create the ads. You can do your other things too.

But that’s really what we’re looking at there.

Gil : Yeah, that’s, that’s so smart because I, I, I’m thinking about it like you’re– what you’re trying to do is like one, you’re not running ads on across the entire portfolio. You’re not, you’re not running ads on the brand, you’re running ads on the properties. And then of that, you’re only running or you’re prioritizing or you’re spending or you’re putting your ad spend on the properties that have the greatest amount of leverage, the one that has the greatest amount of opportunity to fill in there.

And it’s super smart. You’re not, you’re not thinking about just filling last-minute dates, but you’re, you’re looking at the optimal booking windows. I’m guessing there’s a lot of research of figuring out like for this seasonality, this is the booking window. Let’s use that as to figure out like, which are the, the properties that need the most and then look across all the different occupancies.

So like I’m just thinking through like the mechanics behind all that. There’s a lot of math that has to happen behind the scenes in order for it to work like seamlessly.

Amber : Right. Yeah. And then, it, it, and it really like, I, we could go into it for hours, ’cause there, there’s a lot of different pieces and variables and it’s, um … But it, it’s a lot of fun to dig into and it’s kind of amazing that we’ve been able to bring this to the short-term rental space.

Gil : Yeah. What’s the delta between running ads kind of the more traditional way where you’re driving towards the brand, maybe the homepage, versus something as sophisticated as this? Like, what’s, what’s the delta there terms of lift?

Amber : yeah, like I’m gonna say one of the big things that we see is that there’s different types, like, and, and just to, just to kind of go back to the basics here, there’s probably three main types of social media ads, right? There’s, um, organic social, which is like, I’m gonna post something about come visit, um, you know, come visit Sun Valley, right?

Um, and then there’s boosting a post, which is you’ve got this ad, you’re like, “Oh, this ad’s working well. I want to expand who sees this, this, this post,” right? And then there’s paid social. And so we as an industry are real good at social posting, right? We understand that it’s free, right? You just post organically.

Um, po- boosting an ad is, you know, a 50, 100 bucks kind of thing, and we’re kind of used to that a little bit, right? But at the end of the day, the goals of those are just engagement with your webpage. Are you gonna get a booking out of it, whatnot? That stuff takes years to build up, right? And then you’ve got this brand level, and people are used to paid social for brand level marketing of like, uh, you know, the, this vacation rental company exists, right?

Um, that’s great, but like that still doesn’t tell somebody who’s actively looking to book they have a property that, that is what I wanna book, right? They just have to go to your website, they have to dig through it, everything else. What we’re talking about on inventory specific ads are, you know, your company has a property that I wanna book with the details that I wanna book.

And when I click on that, I’m not going to the homepage, I’m not going to the search page, I’m going directly to the closest point of booking, right? So that I can see everything I need to see, which then means actually your time on site goes way down from like minutes to like somebody can tell within 10 to 15 seconds, is this property the property I wanna book?

So they now can see, yes, this is what I wanna book, or this is close, I’m gonna go look at some other properties in it, on this website, right? And so then it gets them in there and it gets them going, and that’s, that’s a different thing that we are not doing. I… There’s some very high-end managers that are manually doing it, um, but not a whole lot just because it’s, it’s a lot of work to pull all the right data in and get those built.

Gil : Yeah. Um, you mentioned something about you’re not driving them to the front door, you’re driving them to the furthest down funnel as you possibly can, uh, which is the, the property page. And then it’d be interesting to see, like, do you drive them… I know you don’t do this right now, but like driving them to a property page with the date selected, that’d be even…

Like I, I’d be interested in like whether or not you’ve done any tests like that. But my guess is that when you are driving them down this far down the funnel, you– the property page has to do a lot more work in terms of building that trust. Because a lot of folks, they use their homepage as a point to build trust.

That’s where the host bio, the about us page, the FAQs, typically those are done on the homepage themselves, the social media links and all that stuff. And now if you’re driving them down to the property page, my speculation is that that property page has to do a lot more in building that trust. And I, I’m interested in hearing like, do you see it the same way or, or not?

Amber : yes. And so that’s where I think reviews come into play, right? And I also think a clean… Like, you– the property page has to do so much work, um, but it also has to be clean, because if it’s too cluttered, it impacts conversion, right? There’s too many clicks, there’s too many steps. Um, so you really wanna, like, optimize, like, does this have everything I need and what I don’t?

And does it give me… It, like, leads to somewhere else. Because the first thing is, is this property for me, right? And that’s a different question than do I wanna book on this website, right? So the– and, and these are– this is a big piece that we’re actually running into that was a big shock for us, was that depending on the market, 20 to f- 40% of people who click on one of these ads to go to the property detail page on the website will book on Airbnb or VRBO because they trust the OTAs more, because they don’t trust the website.

So you have to build trust, right, on this website of they want your property, but they trust Airbnb to fix it if something goes wrong. If they trust Airbnb more than you, they’re– they don’t care if they pay more because they found the right property, right? So just being cheaper is not enough on your website to get that, that booking on your website.

You have to build your reputation. You have to have your… I think your reviews are really critical on your website, um, and accurate reviews too. Like, if, if you see something and it’s got 25 star reviews, that’s not going to… Somebody’s gonna be like, “Oh, they are cherry-picking reviews,” right? You need to have, like, one that’s, like, a three-star review or a two-star review that’s like, um, it rained the whole time, right?

With a good response from the, the manager saying, you know, “So sorry about that. We do have rain insurance at this point that you can, you know, that you can get.” Um, because you– then you’re like, “Oh, okay, like, these are accurate reviews.” So does this look accurate? And, like, that’s 90% of trust, right? Is this property…

Does this property match the experience that I’m gonna have? And is there a local person that is going to address any issues that I have? And can I reasonably get my money back if something happens, right? That’s– those are– that’s what they’re trying to build. So you do have to, you have to build a little bit of that on the, on the, the property detail page and have the rest of it, ’cause they will, they’ll click around, and they, they do a lot of stuff on the, the site after that when they’re serious.

But the first bit has to be, is this what I’m looking for, and do I trust this?

Gil : And do you find that if you found activity, like positive signals that, okay, we’ve sent traffic to this one property page, they’re clicking around. I’m guessing you’re also not just leaving it at that and hoping that they’ll come back. You’re probably pixeling them and, and, and reeling them back in, uh, possibly to the same property.

I’m, I’m interested in hearing like, do you find that there’s more… It’s better to lead them to the same property or some other place or some other property? What’s, what’s been… Yeah, what have you

Amber : Yeah. Um, I would say about a third of the time they will go to different pages. Like once they land on the website, they’ll go to other, other properties and look around. That is, um, it- that’s kind of further along than what Bookings Cloud necessarily does. People will see the ads multiple times. Do they interact with them every time?

What does that look like? Like they probably see them, I think usually our frequency’s in that like two to three range, um, on those Meta ads. Um, and really we’ve just kind of learned like, again, Meta knows you clicked on that ad, you didn’t book, do you need to see it again to book it? They know. So we’ve really kind of geared that to where give Meta enough data, format that data in the, in the way that Meta can use it and optimize it, feed…

continue to feed Meta new data so that it can learn and grow and, you know, build its own, own engine around that. And then like let it cook, honestly. And so getting it like, and the more we’ve actually seen, like we’ve tried to fiddle with it more, the more we fiddle with it, the lower the conversion rates go.

We’re like, “Oh, we just want this property. We just want this thing,” or, “We just wanna like, we wanna reshow this, this many times.” Every time we do something like that, it, um, not every time, but 90% of the time when we do something like that, it actually decreases conversion rates on an actual booking, right?

‘Cause our goal is how much money can you spend to get a booking, right? And that’s ultimately, it’s not clicks, it’s not views, it’s not engagement, um, it’s not time on site. It is can we use this ad dollar to get a dollar in bookings? Can we get to get 6 or 10 or $20 in bookings, right? That’s ultimately what we’re looking for.

Gil : Yeah, you’re looking at the overall conversion, looking at the ROAS o-on that one, not necessarily just the amount of traffic that you bring in. Because if you bring in a ton of traffic and they don’t convert, you’re, you’re not matching the right folks, you’re not… There might be some trust signals that you n-need to address.

So, like, I think the, the thread that I’m hearing over and over again is that, like, m- data’s, like, extremely important if you’re going to be spending thousands and thousands of dollars on ads to generate significant results back. And if you don’t measure the right places, but you also don’t feed that data back into the system that is actually running these ads, you’re not, you’re not just leaving money on the table, you’re actually probably blowing up a lot of money that is run very, very inefficient.

Amber : Yeah. And it’s hard, like, and Meta updates things all the time, right? Google updates things all the time. So staying up to speed with that and staying focused on that and how do you keep your eye on the prize with all the changes going on along the way, um, how they report things, how they measure things, what does that look like?

Like, you have to, you have to stay your eyes on the prize of, like, at the end of the day, how many dollars did you spend to get how many dollars in bookings? And that’s, that’s the, that’s the only game in town, right?

Gil : Yeah. And my guess is that given that you need to have that signal of, like, this person saw an ad and eventually this person booked, that, that conversion tracking there, you have to feed that information back into Meta, otherwise you never know which, which targets are the right ones there. You- you’ll know who, who clicked on it, but you won’t know actually what is the actual end result of it.

Um, and this kind of goes to, like, what we were talking about earlier b- kind of before the show, is, like, what I’ve been seeing, and I’m, I’m interested in kind of hearing your perspective, is that a lot of folks are now, because of the rise of AI, they’re trying to build their own beautiful-looking website out there.

And quite honestly, a lot of them look extremely good. They’re very bespoke. They have custom navigations. They look really good, really elegant. And then I take a look back and I look at some of, like, the structure of the page, the booking flows. They’re using widgets all over the place, and it’s missing a lot of the foundations.

And I’m interested in hearing, like, have you come across the same thing, where folks are trying to almost, like, piecemeal their websites together, but when you’re starting to run mature marketing tactics, that’s where things start to fall apart?

Amber : ん。 Uh, yes, that’s actually a really great question. Um, I would say that one of the things that we see is that w- the professional, like, uh, sh- short-term rental managers, operators, they– they’re used to being entrepreneurs. They’re used to figuring things out themselves, everything else, and so that, that’s great.

It’s a g- it’s a skill that is necessary in this space, right? Um, but then, like, they end up building a website for them that’s beautiful for them, right? First, and that’s a thing. And the second thing, they’re like, “I need more homeowners, so I’m gonna build a website for me that I think is beautiful, and then I’m gonna build a website for my homeowners, um, that gets them to know that, hey, I’m a great vacation rental manager,” right?

And guests are coming in a distant third sometimes. So when we look at this, the, the– we’re forgetting that the point of the website very much is guest conversion. Do… Are people coming to my website, and can they easily find the property they’re looking for? And do they feel confident paying money on this website to check out?

And, uh, when that’s not the main priority of your website, you’re not gonna get as many homeowners coming on because they’re like, “I’m having trouble finding a, a property I like, so why would I wanna put my property on here?” And so just really, like, that– the main KPI of building a website is will it convert a guest who comes to my, my website?

And if man- when managers ask that, the entire world changes on the settings they choose, the extra features they use, everything else. So it’s really going into it with a KPI, like, uh, my goal is to, um, improve and understand, uh, conversions.

Gil : Yeah, I think that’s, that’s so important. I, I’ve– We’ve seen the same on our side where we, uh, we’ve been doing a lot of onboarding, and a lot of them have been coming from, like, the property management co-hosting space where they had a really beautiful landing page, uh, that’s geared towards really the property management side.

And then they come to us because they wanna, they, they wanna bolt on their, their… They wanna, like, leverage their direct bookings. They wanna grow their direct bookings. And usually, like, that’s, that’s the angle that they come in. And it’s almost like having that conversation of, like, reframing them as, like, actually, like, the second-party citizen is actually, like, the, the one that you actually wanna target first.

Because if you create a really good booking experience for a guest, a homeowner is gonna pick up on that. They’re gonna see how much love and attention you put into these properties, how you wanna make sure that the booking flow is smooth. And if you do it the other way around, where you’re talking about your property management, and then you also have a Book Now button on there, like, you’re almost, like, riding both, where the property manager is like, “Uh, this doesn’t feel right.

Like, would I be able– Like, would I wanna book with this stay?” Like, and it doesn’t really convince. But, but when you start to leverage really thinking about how to create the best converting website out there, what are the trust signals that you need to build in? What’s the photography? What are the copy that you need to put in there to really make sure that you’re really targeting your niche really, really well?

Then homeowner starts to pick up on that, and they’re like, “Oh, I can actually latch onto that. I can see myself in that portfolio.”

Amber : A, a savvy homeowner is going to try to create a booking. They’re gonna call your, they’re gonna call your phone number, and they’re gonna send you an email, and they’re gonna be like, “Hey, I have this inquiry.” Like, are they gonna get a response, right? Like they, uh, a savvy homeowner will go through the guest process first, and then they’ll talk to you about homeowner acquisition.

Like if you think about how many, like a- as in operators, how many homeowners you get from people who’ve stayed in your properties. Like that’s just, that’s a regular thing and for good operators. And so you have to… That’s a valid, a valid lead source, right? Um, so yeah, and just kind of remember, like it’s easy to book on Airbnb, right?

It’s easy to book on Vrbo. And so is it as easy to book on your website? Um, can your, can your aunt do it, right? Can your uncle do it? Um, if they’re having trouble, if y- if, if you gave them your website and said, “Can you book this property for these dates?” And they like, can they do it? And what is their experience?

What does that look like? And that’s, those are tests that you need to run on your website and prioritize. And a good website, a good website with the wrong settings, it’s not gonna convert as well. You’ve got to be able to stay relentlessly focused on conversion.

Gil : Yeah. And I think one of the things that we’ve seen, and we talked a little bit about this prior to our call or recording, but what we found is that property managers that kind of try to seek that uniqueness off their websites are often ones that have the more challenging times converting folks. And, uh, like we talked a little bit about this, like oftentimes the guests want to see that this is a familiar booking experience.

They don’t need novelty in the way that they search for stays. Oftentimes it’s harder for them because they’re not using just your platform, but you’ll notice Booking.com, Airbnb, Vrbo, all of those have the same standard way of searching for properties and the same very similar checkout experiences, and that’s familiar to guests.

But if you start to kind of like break that mold a bit, then you make it very difficult. Like I’ve, I’ve seen property managers that have multi-step checkout experiences and it just kills the conversion where they’re later on having to revise and just kind of go back to the basics or go back to kind of status quo.

Amber : Yeah, that’s… People don’t wanna put their credit card into something that’s not familiar. If they’ve never seen this process before, or this is a truly unique website, they’re gonna be like, “Eh, what’s going on? Why doesn’t it, why, why does it not look like what I’ve done before?” So you want a guest to say, “This is the property I’m looking for.

It has the amenities I want. I’m confident that I’m going to get, like, it’s going to meet, it’s setting expectations that are going to match what my actual stay looks like,” right? “The amenities are correct, the photos are correct, everything else. Other people have stayed in it, and they have feedback,” right?

“And if something goes wrong, I can reach somebody who’s committed to fixing it,” right? Those are the things, like, do I trust this with my vacation? Do I trust this website with my credit card? That’s the next one, right? So you’ve gotta solve all of that stuff, and the number one way to do that is familiarity.

So is this what I expect this to look like? If it’s not, I’m gonna start questioning this. If, and especially, and I can’t tell you, like one of the biggest things that we see that is a killer on conversion is when you go to a specific website and it, and it’s then it sends you to the, um… It, like, redirects to an OTA, like booking, um, or not an OTA, excuse me, a PMS, like booking engine, and the URL changes, right?

The URL should be the same the whole way through because they expect that. If it’s redirecting you to another site, where’s my, where’s… Oh, I thought I was paying this company, and now I’m paying this company? What does that mean? So these are things, like, all the way through, would you put your credit card in to this website with this stuff if you didn’t know what was going on?

Um, and the answer a lot of times is, like, no. They’re like, “Dude, I’m gonna go book on Airbnb.” Like, I don’t, I know, I know how to find this property on an OTA, and I don’t have any of this uncertainty, and so I’m not even gonna mess with it, right? Um, you know, another thing I’m actually gonna say that is really a big deal is the payment options.

When you limit your payment options, that it, like, have as many payment options as you can. Um, and because people will be like, “I need, like, there’s four of us that are gonna pay for this we- this reservation,” then they just, they go somewhere where they can do that. It doesn’t matter if it costs more. So yeah.

Gil : Yeah, there’s that, there’s that convenience in there. And I, I agree with you on, like, the booking engine side of things. Like, oftentimes we have some pretty large property managers. They may be on Guesty or Hostaway, and whoever built their site previously are using… Basically, they have these landing pages that link to property pages, and then when you click on the property page, it brings you to the Guesty booking engine or the Hostaway one, and it just really breaks the, the trust there.

It looks very different. The styles are very different. They all have rounded corners where it has a very different design aesthetics than the website that they came on. And it– And I think also, like, on the mechanical side of things, like, it makes tracking conversion really, really difficult as well too, because you no longer have that pixel that’s consistent and the session that’s consistent across the entire checkout experience.

So, like, if you’re running ads, if you’re doing any type of email marketing, it’s really, really hard to be able to trace back that conversion when you’re leading them to a different subdomain.

Amber : Correct. Yeah. The tracking. So the first thing is like, did it happen, right? That’s great. You always want the, you always want the desired action to happen of the booking. Can we measure it? Now that’s a whole… Like, we could have a whole different podcast on how do we measure this stuff, um, and why is, why are, why is measurement directional and not absolute.

Um, like that’s a whole piece that we have. But yeah, like the, when we talk about shifting that and then you have the same client that’s like, “Hey, why can’t you track all this?” And I’m like, “You, your website isn’t even connecting properly.” And they’re like, “Oh, I don’t have time for that. I gotta go deal with my fires ’cause it’s, it’s, I’m in season,” right?

And they miss this.

Gil : it’s not fun to build. Like, it’s not even easy to build a lot of the checkout experience. So like, unless you have a web developer that’s specifically focused on vacation rentals and they’re deeply integrated back into the specific PMS, it’s nearly impossible

Amber : The, um, trying, trying to build some of this stuff yourself, you can do it should you do it, right? Like, and, and I’m gonna go, and I– maybe I have too many cooking analogies. You can make croissants yourself, okay? And I don’t know if anybody’s made croissants here, but, like, you gotta, like, fold the dough over and over.

You gotta do it, like, a million times. To do it right, to get a beautiful croissant, um, it’s gonna take you three days to do. Um, or you can go to the bakery down the street and pay $3, right? And the quality’s the same. And so– and that’s assuming that you’re really good at what you do, right? That you’re, that you’re the best in the game and you understand everything.

So if you understand everything beautifully, you can spend a ton of your time to do it instead of working on your business, you’re gonna build a thing that you can go down the street and buy that’s, that’s at the levels that is what everybody expects. So that is, that is a piece of, like, that deciding whether to buy versus build versus, like, the idea of, like, automating versus not on, again, another podcast, right?

Where we kind of like– uh, there’s a lot of this stuff where as these individual, like, entrepreneurial business owners, you have to constantly prioritize your time and your focus, and you have to decide, like, yes, you can do everything yourself. Does that mean you should? Yes, you can clean better than 85% of the housekeep- cleaners that you hire, but if you’re constantly cleaning properties, you’re never gonna be able to work on your business, right?

And I’m, I’m using that mostly because, like, people aren’t used to… Like, wh- when we talk about marketing, when we talk about building software, when we talk about using these tools, um, sometimes people are like, “Oh, I can do that myself,” or, “I just don’t need to do it,” right? But when we talk about operational stuff, cleaning, y- like, all of our, all of vacational operators are used to, like, being in the weeds about cleaning, right?

There’s ways to set up standards. There’s ways to say, “Okay, that person does, does what I want them to do, and so I’m gonna delegate this.” So you have to decide, and every ma- every manager has to decide: Do I wanna delegate this? Do I wanna get into the weeds? Like, is this fun? Am I doing it because it’s fun to do and I like to do it?

Am I doing this because it’s the most cost-effective way to build my business? And you have to understand it, and a lot of times, yes, you can, like you said, you can vibe code a lot of stuff. But does that mean it’s the best? And then you have to maintain it, right? So there’s, there’s a lot of those pieces, and I think we’re running into that a lot right now with, uh, managers across the board.

They’re like, “Uh, I think I can do this.” And you can. Should you? Is this worth your time, and is it of the quality, and is your business better off for it? So everybody’s gotta decide that stuff themselves.

Gil : Yeah, and you almost have to like, like understand like how sophisticated or how much complexity kind of goes into some of those things, because that makes sense. Like, it could be that you spend five or 10 minutes or maybe even an afternoon on automating some sort of your business because you haven’t found a solution out there, and you know your business really, really well.

But there are also a lot of things that are tried and true that professionals just obsess over. Like, we obsess over conversion so, so much. We have so much visibility across so many property managers that we know, like, if you change it this way, this is how it, this is how it’s gonna goes. Or whenever we’re launching a site, these are the checklist items that we always look for.

And like, if you don’t obsess over it, if you don’t live into it day in, day out, and there’s so much complexities into it, oftentimes we found that you might be investing into something that will give you very, very mediocre, like, impact there. And you can be spending a lot more time on really figuring out what are the parts of your business.

So like, I still encourage folks, yeah, play with it, experiment it, know where your skill sets are, grow your team, and really like, like it’s really good to be in a, a time of AI. But don’t feel like, “Oh, now that I have this superpower that I can do everything and I should do everything myself.” Because like, yeah, you still hire your cleaners because they do it better.

They g- they get that off your mind. They have systems in place, and your job there is like figure out like, again, like what, what you mentioned, like experiment and figure out what to delegate, but also like know what your outcomes are and then like figure out what are the outcomes that you’re trying to do and how do you work with whoever you’re collaborating with to help you meet your goals there and not feel like you have to absorb all that yourself.

Amber : Yeah, absolutely. And that’s, I mean, that’s the whole thing is we, uh, no one person can be a subject matter expert, right? You’re running a business, I’m running a business, our clients are running businesses. We can’t be a subject matter expert in everything, and so we have to like, we can choose to learn how to be a subject matter expert in things, which takes years, right?

And to do it mediocre, like, uh, like, or we can like find who knows this, who obsesses over this? Let’s pull that subject matter expert in to consult on the thing that we need to build, but keep a really good strong eye on what do I want my business to be, and how do I prioritize all the things that I need to do to build my business and where it needs to be?

And that’s that, like, that’s where business owners should be relentlessly focused. How do I build the best business I can build in the direction I want it to go and, you know, build those things? And yeah, vacation rental managers have this legion of subject matter experts in guest communication, owner communication, websites, marketing, like, uh, housekeeping management, like operational stuff.

There’s all these like softwares, but backed by people who are subject matter experts, right? So like, who love to talk about it. That’s what we’re doing. We’re sitting here talking about things that we love to do and that we like get really into the weeds about, and we’re constantly tweaking and adjusting.

Like, talk to, yeah, talk to the subject matter experts around you and skip the learning phase, right? And that’s gonna make your business better because your focus is your business.

Gil : Yeah. And I, I feel like there’s like this point where the property manager starts to leverage a team. They’re starting to hire individual. They have a head of ops, they have a head of marketing. Those are the types of property managers that when we work with, there’s this level of maturity of knowing like, “Okay, I need to spend in order for me to have the impact that I want.”

And they’re not trying to boil the ocean and try to keep everything internally, and they don’t try to make them the bottleneck. They know how to leverage other people, either internally or externally, to help grow their business. And those for us have just outside– On our side, specifically on direct bookings, they have outside returns on direct bookings.

They have phenomenal direct bookings because they brought in experts either in the industry or they’re heading– they’re hiring a head of marketing that all they do is obsess over these types of things. And so like I, I, I’m– We’re seeing tangible impacts on folks that have like the different mindsets. We, we, we s- we love the builders, but we also see like people that are knowing when they should build versus when they should hire in or out.

Amber : Um, 100%. And like one of the things that I’ll talk about, right, is like specific examples. We have a company in the Outer Banks that’s been one of our clients for, you know, for a while now, and they are, their name is known, right? They’re like, um, their brand is known. Their properties are the best properties in their, on their beaches.

You know, s- they can do seven night minimums during the summer, like Saturday to Sat- like they get, they get to state the rules ’cause they

Gil : They commanded

Amber : They, they are the oldest of old school on this, but delivering a great product and a great quality product And we brought them on and we got them more visibility.

And because their brand is known, because their properties are the best properties on the best beaches, right? We’re– the, the trust factor isn’t a factor for them. Everybody knows them ’cause the people that go to the Outer Banks, they go every year, right? They know who they are. So you’re just reminding people, by the way, this company has the property that you’re with the, with the amenities that you’re looking to book.

So instead of going to all the other websites, they’re just like, “Oh, I’m gonna click on that and I’m gonna go ’cause I don’t have the… ” Their return on ad spend, and it- they’re not spending enough money, and that is clear, but their return on ad spend is like 100X. So they’re giving us a dollar and we’re giving them $100 in bookings, right?

For every dollar. And that’s an insane number. And the traffic going to their website is huge, and the quality of their traffic is huge. So they’re getting a ton of people clicking on these ads and going, and they can actually see, ’cause one of their things, they were major direct booking. They’ve always been focused on direct booking.

So like 70% of their bookings were direct. And their goal was, we need new blood because all of our people are, they’re older. They’ve been booking with us for 20 years. We need fresh people. And so what we saw when we dug into Meta was the demographic was 35 to 44, was the main people booking, and they were booking the trendier beaches, the newer beaches where the, where the young, um, not that, you know, 35, 35 to 44 is young, but that like where the young people were going, right?

So they could actually see visibly, and this is like month two, right? Oh, the demographics are younger of the people interacting with these ads. We can’t tell who’s, which, which bookings were… Like, we can tell you how many bookings, um, were interacted with an ad before booking with, um, with the client, but we can’t tell you exactly which bookings they were because of privacy laws, right?

But we can say the traffic you got was significantly younger and the beaches that you’re getting bookings on, um, new– that your booking velocity was higher in these trendier markets, right? So we were able to establish that, and that is different from a company that is still trying to figure out what it wants to be when it grows up.

Like we have a, we had a company with, again, a website that they built themselves, that they, um, they’re in like six different markets, but they don’t have, they’ve got like, you know, no more than 15 properties in each market, and the markets are all in different states and they’re still trying to figure out how to focus.

So their brand is not, they don’t have a clear brand, right? They might have a logo, they might have that stuff, but they’re defined, here’s what our guest ICP looks like and here’s what we’re looking for and here’s what our homeowner ICP looks like and here’s what we deliver. That’s not focused, it’s scattered, right?

We send people to their website, but they don’t book ’cause they don’t trust the web- they don’t trust the properties and it’s kind of all over. They’re like, “Oh, and if this property doesn’t work, there’s no other one to book,” right? So this one, like we can send the money. The return on ad spend is probably, you know, in a high booking, it’s probably six, right?

Gil : うん。

Amber : and we’ll give you $6 in bookings, or we, we can, we can connect $6 in bookings to that. It’s lower because we’re having to figure out who, like your ICP is, is scattered, your brand is scattered, your checkout process is scattered, and your trust is not entrenched in that, in that site.

And that’s just the experience. These two, like these two companies, you know, I, um, they’re different ages, right? But, and they’re two extremes. And so we look at that and we see when you get, when you don’t work on your business and focus on your business and you can apply this, the results may vary. And I, and I’m sure you see that with websites of the results may vary. And it’s not, it’s not the software, it’s, it’s the focus. So focus on building your business, focus on building your ICP, focus on understanding who you wanna be when you grow up. And I, and like, and, and I hate to say it in that term, but that’s, I mean, that’s, that’s what we work on, right? What’s the vision for your business?

What does it look like in three to five years? How do you take the steps to get concentrated so everybody can speak to what your business is? And focus on that relentlessly. And then Gil, you focus on conversion on the website, and I focus on driving traffic to the website so that you can convert it so that people like love this brand and you’re building the quality of this brand, which then makes this brand valuable, and then people wanna buy it.

And now you’ve got an asset versus just a company that, um, books webs- that cleans houses that are listed on Airbnb. The range that we get from a co-hosting properties booked exclusively on Airbnb, which there, there’s value to that, right? To an established company that people will fight over to buy from you.

Like that ra- that’s what, that’s what we’re all building as entrepreneurs, right? That’s what you want. Even if you’re not gonna sell it, like that it has value and it, it’s bigger than

Gil : has sustainability. Like, I, when you have, when you have really good distribution across all your different channels and like, I’m not to say like you have to be 100% like direct bookings, but like make sure that you’re not like heavily concentrated 50% plus on Airbnb, for instance. Like that’s almost like the status quo for a lot of folks nowadays.

Amber : Угу

Gil : of eggs to be putting, putting into like one specific basket there. And even if it has really healthy revenues, there’s, there’s a huge risk there that, I mean, we’ve seen this in 2025, where Airbnb had released like four different changes that negatively impact the property manager and host experience there, where we have less leverage, where they’re having us fight for our review distribution.

Like it’s, it’s really challenging more nowadays than ever before. And the property managers that are growing their direct bookings, they have much greater control on whether or not they’re able to command the bookings that they need and want. Um, they’re able to influence it much better rather than just playing the price game where if you wanna go on page one or two, you lower your price on Airbnb and that’s how you get there.

That’s the only lever you really can pull

Amber : Mm-hmm. 100%. And so it’s– And again, those margins are gonna continue to get compressed. And so, uh, the, the businesses that last going forward are the ones that build a diversified revenue source, and they have more control over where their revenue comes from, and they can adjust, right? ‘Cause right now, yeah, if, if you’re, if you’re entirely focused on one distribution channel, they get, they’re calling the shots, not you. So then what are you building?

Gil : yeah. Yeah. I have one last tactical question for you o-o-on this one. Um, we run– We’ve been doing a lot of investments in like email marketing, um, specifically, and one of the things that we’re targeting right now is… I come from e-commerce, and one of the very standard things that we all do is cart abandonment.

You add something to your cart and you don’t finish a purchase flow, and we send them an email to come back. I’m interested in hearing on your side, have you done any experiments on kind of the cart abandonment on the ad side of things and, yeah

Amber : No is the short answer. There’s so mu- there’s so much ground to cover. Yeah, we, we’re not there yet,

Gil : Yeah. That’s, that’s, that’s a project I would love to, to kind of play around with, with you folks because there’s like, you folks have this level of maturity and complexity in kind of how you run ads. And for us, we’re already capturing all the signals. We’re sending it to the email service providers. We can very much send those same signals.

Like, we know the guest email address, uh, if they’ve started the, the checkout process or they’ve done a lead magnet on there, so we know that. We could, um, we know which properties they looked at, what days they stayed in as well too, or they selected in there. So I can imagine that, like, if you were to send an ad specifically for that specific stay, that booking window or the, the days that they selected, I’m interested in, like, what the level of lift is to kind of get that person to convert.

That would be a fun project for us to work on together.

Amber : Um, we’ve done some testing, right, on this, and what we’ve found is the ads, the way we’re doing them right now are so far and away the most effective way, and it picks up some of that remarketing al- automatically. It’s, it’s not, it’s not focused, right? Um, but what we’re seeing is it’s so much more effective and there’s so much room for, um, managers to just like, let’s get these ads out.

Like, that’s a refinement after the fact. So we’re really working on like, what is the, what is the quickest way to turn a dollar into $20? And how do we get that going? And there’s, there’s opportunities to do that in the, in the short-term rental space right now, which there’s not in a lot of other markets, right?

If we look at e-commerce, there’s n- there’s no opportunities to market something and turn it. There’s, there’s an opportunity to turn a dollar into a dol- a $1.60, right? And so there, there’s all this space to run before we need to even start getting that refined. Like let’s get s- yeah.

Gil : Yeah, you’re right on that. Like, there’s, there’s already so many, not– I don’t wanna say basic, but there’s things that you’ve had tried and true and that works really, really well that hasn’t even been… Like, not a lot of property managers are e-even doing those types of things, so there’s just this outsized return that, like, is readily available to you.

And, like, once that starts to be, like, saturated enough, like, we can start going down the, the funnel there and, and optimizing even more. Yeah, I can see that.

Amber : Really, um, looking forward to that

Gil : Yeah. Amber, we usually end the show with three questions. Um, I’m kinda throwing you th- on, on this one by surprise, but, um, the first question I have for you is what’s a good book recommendation?

Like, I’m always looking for a book, a good book. Maybe what’s a, what’s a book that has really inspired you?

Amber : Um, oh, so now you’re go- like, I, I’m gonna confess to a couple things. One, because I do so much work right now, like I go, I go in like learning phases and then working phases, right? So right now a lot of what I read is very casual stuff, um, that’s just like resting phase, and I think that there’s a lot of value to that.

But, um, I’m gonna say the one book that I’m reading right now is “Supercommunicators”.

Gil : Okay. I haven’t heard that one

Amber : yeah, so it’s really about like how do you communicate effectively across different types of people, right? And that’s one of the things that we try to do. Like we work with different, different m- like mindsets, right?

Like we’ve got revenue managers and marketers, and I’m gonna say revenue managers and marketers might as well be speaking like French and Chinese to each other sometimes, and they should be working very closely together. So how do we talk to revenue managers and marketers who have different, entirely different like, like tools to communicate, like value points, everything else, and how do we do that effectively, right?

So this is like one of the things I’m trying to work through. And, um, just so like how do we communicate better? How do we use our words better to, um, effectively build buy-in, educate, spread awareness, all that kind of stuff. So that’s, that’s a big piece that I’m working

Gil : Yeah. Yeah, it’s almost like pulling that person into your world and vice versa. Giving them the bridge to pull them– pull you into their world as well too and understand each other.

Amber : Yeah. And like, uh, one of the things I really prioritize is building a diverse team of different thoughts, like perspectives, so that we can see like, does, um, does somebody else see something that we can fix that maybe I don’t see, right? And so if- so we’re all looking in different directions in different ways, which requires extra communication, and how do you do that remotely, right?

So that’s, that’s a big piece.

Gil : Yeah, I, I love that one, especially like the last part of like growing at a very diverse team. Like last night we were, we were chatting, we were having our stand-up, and w- my head of engineering like pushed back on me pretty hard, and I was like, “Okay, actually you have a really good point.” Like I actually, I acquiesced.

“You– Let’s do it your way.” And I– And like that’s, that’s, that’s like the culture that you wanna build within your company as you’re, as you’re growing it. So I value that.

Amber : Yeah, absolutely

Gil : awesome. Amber, second question I have for you is what’s one piece of mindset advice that you would give to someone that’s starting something completely new?

Amber : Um, if it’s your first time starting something completely new, I think the thing that struck me back in the day when I was first building something new was you will not be able to do… Like, you’ll be able to identify what you need to do, um, in, in a level that far exceeds your capacity to actually do it, right?

So understand, like, your 100% is probably overdoing it. You probably need to be at, like, and you have to figure this out, 70%. And you’re gonna deliver a product for a long time that is not at the quality level or the expectation standards or the comprehensiveness that you want, or deliver the customer service or whatever it is at the…

You know it can be better. Um, and you’re not gonna be able to do it, right? And that’s why you’re gonna be good at what you do. So one, you’ve gotta figure out what to, where to start, but that gap between where you are and where you wanna be, that’s what makes you better because you’re striving for that.

The people who just stop at adequate, it’s because they don’t see a gap in where they are and where, where they could be. So understand that that’s part of your super- Like, you’re gonna be frustrated about it, but that’s part of the superpower. That’s what’s gonna make you better because you’re constantly moving forward and improving where…

And that’s gonna make your business better and your project better.

Gil : Yeah. Yeah. In software development, like, any entrepreneur that looks back and they’ve built their business and they’re, like, two or three years deep into it, they look back at their first iteration of what they launched, and they’re embarrassed by it. Like, I, I, I remember Craft-us-Days, the, the, the first version, I was the one that coded it, and I compare that to what we have right now.

Oh my God, if I,

Amber : उहम्।

Gil : if I had put my objective of, like, what, where we are right now and that was the mark, and if I didn’t hit that mark, I would have given up a long time ago. But it’s like that iterative, like, grit of, like, knowing where that vision is and slowly building towards that, and you’re not gonna get there overnight.

You might not even get there in a few months. For us, it took like… We’re now, like, two and a half years deep into it, but our foundation is so strong right now, and the things that we’ve learned along the way h- is, is so valuable to us, is that we’ve built that momentum over time. But it, again, it took time to get us to where we are

Amber : It’s the first version of whatever you build, you should be a little bit embarrassed by. And if you’re not, like either you took too long or, or, you know, something like that. And that’s, that’s really a piece there. It’s, I totally agree,

Gil : Yeah. Awesome. Amber, last question. We talked a lot about really a lot of the stuff that you do in, in terms of running really, really targeted and highly leveraged ads. We talked a lot about direct bookings and building trust. What’s one tactical advice that you would give to anyone that’s either trying to get started in direct bookings or amplify that direct bookings?

Something they can do in, in an afternoon

Amber : if they already have a website? Yeah,

Gil : Ja. Ja

Amber : Um, like go through, like go through your website, go through your checkout process all the way through from like, a finding the property all the way through the first guest email, the second guest email, the third guest email, the check-in instructions, all of that, like from the customer experience, right?

We so often look at things from the operating experience, we forget what that looks like from the customer experience. Are you building… Your opportunity to build a brand, the best opportunity is after the booking. Does that first email, that first communication, that interaction with the website, all this stuff, do you– have you looked at it not from your perspective of what you want, getting your job done, but of the client’s perspective, the cust- the guest or the homeowner, right?

Look at it from that perspective. It doesn’t cost anything to do. Um, but when you understand that, you’re gonna be able to see 15 things that you need, you wanna tweak, and it can just be language, right? Timing. Um, you know, are you building that trust? So, um, like that’s the first thing I would do. The second thing is reviews, right?

You are… The first 10 reviews are critical for every property, right? You need to have probably four and a half stars average or 4.8 stars average, right, on your properties. The first 100 reviews, they– that’s what makes you more money. The more reviews you have on your properties that, like the more money that property will make.

You have two identical properties, one has zero reviews and one has 20. The one with 20 reviews is gonna do $15,000 to $20,000 more in revenue in a year, period. So, um, anyway, that was two things.

Gil : Yeah. Yeah, yeah. I, I really like you really putting this per- per- perspective because a lot of times we’ll iterate on things. We’ll find out like, “Oh, this guest asked this. I’m gonna go ahead and add it to my welcome email or our guidebook or whatnot.” But it’s often not, not the first thing that comes to mind of like actually going through from start to end and like what that experience looks like.

And I would even like even extend it and say like, have your partner do it, because your partner will give you very candid advice. They’ll give it to you very straight, and they don’t have that foggy glasses on of being an entrepreneur and, and, and, and that almost jaded look on, on it. They’ll give it to you very, very straight on things.

I know my… Definitely my wife will.

Amber : A- absolutely. Like, and, and so I guess I would say you wanna keep iterating on this. It’s the first one, you do it, then you have your partner do it or somebody who’s gonna give you unfiltered information, and then you have somebody who’s not tech-savvy do it. And that’s the next step on that. And then, like, then you’ve got it down

Gil : Yeah. Yeah. Awesome. Amber, it was a huge pleasure having you on the show and just dissecting all the things that you do. Like, when we met m- the few times in the conferences, like I, I knew that there was something different about the way that you guys run ads and the complexity and the technology that goes into it.

So it was really fun to kind of like be able to pick some of those things out and really like highlight what a sophisticated system will look like and kind of open folks’ eyes on we have been living in this world of hospitality for so long. We, we see what’s available out there, but if you start to look at different industries and look at how other people are bringing the technology, there’s actually a lot more levers that haven’t been tapped yet.

So I appreciate you and you coming on the show and sharing that with us.

Amber : Yeah, absolutely. Well, thank you for having me and the work you’re doing at Crafted Stays. I really think, um, making it easier to access really great converting websites is, um, critical in the steps forward as, as our industry evolves and moves forward. So

Gil : Yeah. Uh, I look forward to working with you more. Thanks.

Amber : Absolutely. I love it. Thank you.