Why the Future of Vacation Rentals Starts with Better Operations with Jeremy Gall of Breezeway

Jeremy Gall 0:00

Every property is unique. Every property manager is unique, but we can't have all of these unique, crazy fields. It's very difficult to fully automate because you're dealing with so many humans and with so many exceptions.

Annie Holcombe 0:11

With some of the automation that's going to come into play, some of the AI that's going to come into play, there's going to be some money that's freed up that think people could put towards really paying the staff. I've had to clean rooms before and it's just not fun.

Jeremy Gall 0:22

We're approaching about 100 million tasks that have been completed through Breeze Bay. Over hundreds of thousands of units. Tons of data about like how operations are done and the pattern recognition of like what's about to go wrong.

Alex Husner 0:35

You know the industry very, very well. How come you guys haven't ever just decided we could build out the rest of the stuff and we could just be the PMS?

Jeremy Gall 0:41

That's a loaded question. That's a loaded question.

Speaker 2 0:45

My name's

Sponsor Spotlight: Savvy

Speaker 2 0:46

Mike Nord. I'm the director of third-party partnerships at Inhabit. My role is basically to sign new partners and help them grow within our ecosystem. We've been integrated with Savvy going on about four years, and it's been a great partnership from the beginning. They're everything and anything that you want in a partner. We attract the most forward-thinking PMs, the ones that are tech savvy and the ones really looking to increase their direct booking presence. We're always looking for great new OTAs to come in and kind of help enhance that direct booking strategy. And Savvy's been the perfect partner to kind of help us encourage our PMs to get more direct bookings, retain their guests, and really keep more money in their pocket. PMs are really heavily reliant on a couple of channels. And so the industry and in general have been hungry for another partner that can capture new travelers, capture new bookings. And so a partner like Savvy is exactly what PMs are looking for in terms of getting more of those direct bookings, getting more of those travelers, and retaining those travelers going forward. Right out of the gate, Eric has been in the industry a long time. He recruited some of the best talent in the industry to help him along the way. And I think that's part of the ingredients of what makes a successful channel is having that industry knowledge within your staff. They came out of the gate knowing what they were doing, having a plan, and really going after it. I really appreciate the partnership that we've had with Savvy, watching them grow from sign-up to over 200 PMs. They basically set the record in terms of property management signups in their first year, and then they started getting the bookings. They backed up what they promised. They've been really incredible to work with. And I really look forward to what's next for both of our companies together. Would I recommend Savvy? Yes, I would definitely recommend Savvy to any property manager looking to get more control over their direct booking strategy, get more guests, keep those guests, get more repeat travelers. I think they're a great portal, easy to set up. So 100% I would recommend savvy.

Alex Husner 2:39

If you're looking for a distribution partner that's actually built for you, not around you, check out savvy at savvy.com/slash Alex and Annie. Welcome to Alex Nitty, the relevant of vacation rentals. I'm Alex and I'm Annie. And we are joined today by Jeremy Gall, who is the CEO of Breezeway and a longtime guest that we've can't believe we haven't had on the show yet. So it's about darn time, Jeremy. It's so good to see you. Thanks so much. Thanks for having me.

Jeremy Gall 3:09

Excited to be here.

Annie Holcombe 3:09

Yeah, I we we were talking about that, that we haven't had you on. It feels like we have, but maybe we just talk about you a lot. I don't know.

Alex Husner 3:16

It could be. We have to talk about Breezeway all the time, I will say.

Annie Holcombe 3:20

Yeah, we do talk about Breezeway all the time. And then, like you said, you know, we we talk to Corinne quite frequently. She's been on a lot. But it's great to finally have you on. And for those people who don't maybe know Jeremy and kind of your history, why don't you give us a little bit of your background to present day?

Jeremy Gall 3:33

Sure. Yeah. I started in vacation rentals in 2006. I started a company called FlipKey Vacation Rental Marketplace. Our big insight was thinking about like brand recognition for property managers so they could differentiate themselves from individual owners and rent by owners at the time and how they were working. So we built FlipKey into a pretty large marketplace, partnered with TripAdvisor and Expedia. Benefit of that was I got great exposure to thousands of property managers who I got to be really close to their business, close to them personally as

Building a company property managers want to work with

Jeremy Gall 4:10

well. And that was really my introduction into the industry. And then did that for a number of years, stayed on post acquisition by TripAdvisor. And then left and started to think about like the vacation rental industry and what I had learned and what I had learned from my friends and the and the partners that I'd built while we were there. And thought a lot about the future of vacation rentals and what was happening next at this time. This is around um 2014. And thinking about how service was changing, I'd seen we'd seen this happen at Flipkey where like people were just, and you've lived this, Annie, like, you know, um, guests were becoming more discerning, vacation rentals were being cross-shopped with hotels, service standards were increasing. And um built up a thesis that if we could help property managers do a really better job and sort of optimize how they thought about their operation, how they thought about service, we could have a very positive impact on their business. And so started Breezeway with the thesis around operations and service management and what it's like to actually do this work and deliver for the guests. And I would say, like me personally, you know, during that time, we picked up a vacation home in South Carolina, and I had a lot of exposure to like how that worked and dealing with guests and thinking about property maintenance and like the hassles of maintaining property and what that was like. You know, so happy to dig like more into that if it's interesting.

Alex Husner 5:43

Yeah, I I remember the very early days of Flipkey for sure, back when I was at Condo World. And um, that was actually probably just when I had started in uh 2009, I'd say. And, you know, back then everything was email related. I mean, we like lived and died by those requests. And, you know, the funny thing is actually, I don't know if I've told this story on the show before, but we were getting so many of them that we created our own. We called it the lead manager at the time, that it was kind of like a unified inbox because there were just so many coming in and we couldn't figure out who had responded to which of the leads. And uh, you know, fast forward to now and what what a difference of how things operate. But it's been fascinating watching the journey of Breezeway. And the one thing that that always stands out that we hear, and even though we haven't had you on the show, like I said, we we still hear Breezeway's name all the time. But I've never encountered a customer that doesn't say that they love working with Breezeway, which, you know, normally every vendor has a few squeaky wheels. I'm sure you do, but the majority of your customers are obviously very happy and and they speak on your behalf, which says a lot. But I'm just curious from that lens, you know, how do you how do you build a company like that? Like what is the secret sauce, do you think, of why you have so many people that are willing to be, you know, advocates shouting from the rooftops about what you guys do?

Jeremy Gall 7:00

Yeah, I mean, I think that's so kind. I'm sure we've let some people down, even though we we do our best not to. Well, we learned at Flipkey, we made a really conscious decision. Um, and I think it it worked for us that we wanted to be the platform that property managers loved. And we wanted to show up at the events, we wanted to build personal connections with those managers, we wanted to really care about their business, we wanted to overinvest in client support um as best we could so that we became like the preferred channel. And at the time, especially like 2000, 2008, 2009, this was like, I guess maybe it wasn't that hard. We were trying to be the preferred channel versus home away, and home away done a pretty good job positioning themselves as the bad guy. And so um maybe that made our job a little bit easier. But we just saw the benefit of doing that, that like this is uh an industry of folks who recognize when you care about them. And so if you can do that and you can demonstrate that care and like attention to the business, people will reward you for it and they will they'll work with you and they will be your advocate and they will be um really good partners. And so I don't know, I think it's a philosophy, and we're not alone in this. I don't I don't know if that's like a super special insight. I wish there was like a different silver bullet, Alex. But um you know, I think that uh people pick up on that, which is why there's a lot of love for vendors in this industry, and I think a healthy appreciation for technology and like the tools that people use. Um, but you can tell the companies that sort of embrace that and and the ones that don't.

Annie Holcombe 8:38

We've been talking about this a lot lately, I think, relative to AI coming into this space and where people find the balance in using it. Um, but the one thing that just holds true regardless of how much technology comes in is like this is a relationship business. And the more you can kind of focus on that relationship, I think that's where people are gonna win. I mean, you can have great technology, but if you're not really supporting the people, it doesn't matter. They're they're gonna feel left out and they they feel like they're out in the field, you know, without support. So I think focusing on that is is never the wrong, wrong way. And like you said, it might not be a silver bullet, but it's it's unfortunately, I think too many people have gone away from actually providing customer service. I mean, if you look at, you know, things people will post often about um, you know, you you get stuck in a loop of the AI bot and, you know, you know, on a website or on a phone call, and and people get more frustrated by that. And I said, so I think that if people continue to focus on building the technology but still providing that support, it's it's a balance that you can win with.

Jeremy Gall 9:34

Yeah, I think that's I think that's definitely true. It's tricky too, though, because um AI works not only to drive efficiency within the companies, but like we're all becoming more accustomed to being able to answer our own questions. Right. And so I think that also means that people like to be able to like solve their own question. Like I have a support issue. I don't really want to wait around for somebody to solve it. If I can solve it myself and I can ask the question, as long as I get a good answer and I'm not frustrated, I think about transparency and needing being really particular and careful about how you meet your customers with automation or without. And I think that's pretty much applicable in the vacation rental industry.

Alex Husner 10:18

Yeah, and I think one thing that's important in this too is that the companies that they are also really listening to their customers, and Annie, I hear you say this all the time now in your WordKitbooking.com, but um, the companies that are listening to their customers and are actually taking their feedback and you know, applying it or at least putting it into, you know, uh looking at what other customers are seeing and saying, okay, maybe this could be done a little bit differently than you thought, and like this is what we're working on, just having that collaborative nature with your vendors, I think, is is huge. And that does build that, you know, that trust and that tether to, you know, to both companies. And it sounds like from what I've heard, that that's how you guys really got started and have continued with it. But I'm I'm curious on the early days of Breezeway. I mean, what what did you know about operations as far as vacation rounds when you got started? Like, did you know a lot about it? Or like like how how did you come up with that idea? And like what made you think like, aha, I'm going for the operations side.

Jeremy Gall 11:18

Yeah, it's not really something people probably pay that much attention to. I think that's where you have to, that's that's how you have to hunt out the best, you know, the best opportunities. It was truly, it was truly, Alex. I was frustrated with maintaining my own primary home and thinking about like the maintenance that it takes to maintain my own primary home and thinking about solutions around that. And like, could there be opportun this is you know, 2014, 2015. I'm thinking about are there technology solutions that would make this like easier for me? Like, how can I how can I be better at this? And while I was doing that, I was like, huh, this is really interesting. Vacation rentals have a

The early days of Breezeway and connecting operational workflows

Jeremy Gall 12:00

huge, you know, they have a massive problem with this. They have this problem at scale, and they have to maintain these homes. They're all unique, they have unique owners. Every guest stay is a unique stay that they're preparing for. And so truly, I just called up my friends in the industry and I said, I I just really want to learn everything about your maintenance programs and your operations programs. And I went and visited some of them. Some of them flew up to Boston and spent a couple of days whiteboarding sessions with me to sort of get the idea started. And that turned into, you know, a thread that we just kept pulling. And that was not easy because um I think I was a little naive at the beginning because I didn't know that much about operations. And once you start getting into it, you start to realize this isn't a discrete problem. It's broad and it's also incredibly deep. And it can't really solve the problem for folks unless you cover a lot of surface area. So it wasn't it wasn't an easy build, but it was true that this was something that was bothering. This was a problem for a lot of folks in the industry. And I think it's still we've helped, but I still think there's like a ton of opportunity and still more that can be done because this is a thorny, this is like operations and the service that people provide. This is what makes property managers special, in my opinion. This is like what hospitality is, and would love to, you know, we can talk a little bit about that. The more you could, the better you can be at this part of the business, the more it helps drive owner satisfaction. It clearly drives guest satisfaction, and it is basically like the entire basis of your business, other than like your you know, big marketing discipline.

Annie Holcombe 13:45

So take us through what that looked like when you were ready to kind of start going out there and working with people. Because I know I was in property management, was I left property management in 2011, ended 2011. So I I we had been through so many iterations of like, okay, well, do you give everybody phones? Do you give everybody radios? Do you have a board in this office? Do you what you what do you do? Do you have them log into the, you know, log into the PM spreadsheets for days, like all these things. And there were just so many, so many ways to try to do it. But it was like really like, where can you save time? Where can you communicate better? Like all these things. So I think, you know, you were providing an answer, but but to your point, everybody was kind of operating in different ways. I mean, you know, what people, certain levels of service. I mean, you look at a luxury, you know, uh, houses versus condos, those types of things, people that are serving multi-markets. I mean, let's face it, like a market like Myrtle Beach or Panama City Beach, just trying to get from one end of the market to the other during busy times that just you're just wasting a lot of time in cars.

Why property managers should think differently about their relationship with the property

Annie Holcombe 14:40

So this is where, you know, a lot of this can help. So take me through like those first meetings that you had with property managers to pitch them on what you were doing. How did that go?

Jeremy Gall 14:49

Not well, not well.

Annie Holcombe 14:50

He's laughing. It must not have gone well.

Jeremy Gall 14:53

Several did not go well, I would say. I think there was like there was just the sort of feeling of like, holy smokes, like you built Flip Key and you tackled this like marketing problem where there's a lot of booking dollars. You know, there's a lot of dollars at play helping drive bookings. Like, why on earth are you getting involved in operations?

Alex Husner 15:15

You lost your mind. Stay in your lane, will you?

Jeremy Gall 15:20

There was plenty of this doesn't make any sense. But I just I couldn't sort of I just couldn't really shake it. And the more people I talked to, even though, yes, I think we we we the early conversations, we faced a lot of resistance because um people do the job differently. Uh and to make a change to your operations, you had to cover a lot of ground. But all of that just sort of reinforced the opportunity and honestly just gave us like gave me and the early team more confidence that this was not a feature for another platform, but truly like its own product. And I think a lot of that resistance came from like learning hey, well, my team does it this way, or like cleaning is really important, but cleaning, you know, I might do I'm not using anything for my cleaning team and they don't really need anything, but it would be helpful if they had checklists and like better workflows. But my inspection, my inspection team is using this like one tool, but all it does is inspections and they're totally disjointed from the cleaning team. And if they notice something from maintenance, like definitely the maintenance team is not in the inspection software. And like that was a very early learning that was the way that you can tie the workflow together completely between cleaning and inspection and maintenance so that the entire back office operation could actually be cohesive, opened up a lot of value to property managers. That was like one really interesting early learning. And another was um we really leaned into the concept, and we still do, that property managers should have a relationship with they have a relationship with the owners and have a relationship with the guests. And I still think there is a little bit of lack of recognition that they have a relationship with the property. And they have a really special relationship with the property that I think most property managers don't take enough advantage of, which is like if you're my client, um, Annie, like I know your property better than anybody else. So why would why would you ever leave?

Annie Holcombe 17:30

Right. So now you're saying like, so we have to worry about guest, guest personas, owner personas, and home personas. Like that's that just that's the same property personas. Like that's a whole like that's a whole like that just blew my mind. That's a whole new series for me, Alex. It's gonna be Yeah, exactly.

Alex Husner 17:47

Yeah, if if this home could talk, right? You know, exactly. Even if there's a vacation rental right now, and I can guarantee if this home could talk, it would be saying, Everybody keeps telling me that my Wi-Fi sucks. My phone right now. My communication skills are bad. Yeah. And so the property manager should be over being like, come on. Um, but no, I think that's a really good point, Jeremy. And I haven't heard anybody, I've I I mean, I understand the concept of what you're saying, but I haven't heard anybody say it exactly like that. But you know, it kind of loops back into, I mean, when when you hire a property management company, depending on how the property management company is set up, if you have one property manager that is responsible for your house and that's the main point of contact that you have, then that is what you should be seeking for, is that that person knows everything about the house. If they

How rising guest expectations are changing vacation rental standards

Alex Husner 18:35

drive by and they notice that the, I don't know, you know, there's something wrong with the landscaping or the blinds are open or the door looks like it's got, you know, scratches on it, they they'll notice it. And to a homeowner, if they are keeping on track on top of that, I mean, like that, that is impressive. You know, like I really have nothing to worry about. They've got my best interests at heart. Um, but I think that's hard. And I think that comes down to uh, you know, companies are set up so differently to your point of probably when you were out there pitching this initially, that you know, the company that I worked for for many years, there were two property managers for 500 properties, you know, and those condos, and like it was that was somehow feasible. Um, but a lot of companies, you know, these days with beach homes, it would, it's, you know, they have no more than like 30 properties, or it just depends on what the inventory size is. So the level of how somebody can really be giving that care is is a little bit complicated. But how did you, you know, knowing those complexities of just different business models, how how did you then build the product to be able to speak to how different it can operate?

Jeremy Gall 19:40

Well, we had the advantage, I think, versus, and this is, you know, I know that a dynamic that continues to evolve in the industry, but we had the advantage of just focusing on back office operations, which sort of counts the mandate significantly. We didn't have to focus on reservations and managing the calendar and rates and channel distribution and then optimizing for those channels. We had the benefit of being able to think about okay, everything after the booking, like what happens and what's the what's the workflow and how can we address that and build deep features and functionality to help drive some value there. And again, like really thinking about and I, you know, I think I'm a tough critic. I think there's a lot more we can do. I think we're so pretty early candidly on the journey of how we can help people do that. I think there's just so much more to do. And when you think about that, how you maintain that relationship with the property and how you truly help the owner understand the value that you deliver as a property manager. We've built some great tools to do that, but there's a ton more that can be that can be built to help property managers really, really showcase the work that they're doing and their relationship with that property.

Alex Husner 20:58

One thing that really came through in today's conversation

Sponsor Spotlight: Breezeway

Alex Husner 21:00

with Jeremy is that great hospitality depends on everything happening behind the scenes, the work that guests may never see, but absolutely feel during their stay. And that's where Breezeway really comes in. Breeze Way is an AI-powered property operations platform that helps short-term rental and hospitality teams manage cleaning and maintenance, automate repetitive tasks, catch problems earlier, and deliver a more consistent guest experience. This fall, Breezeway is adding even more AI agents to the platform. They'll help assign work, alert the right team members, and address potential issues before they ever become a problem for the guest. The goal isn't to take people out of hospitality, it's to take some of the administrative work off so that they have more time to focus on the guest. Breezeway already powers operations for more than 350,000 properties across 90 countries. It truly is where hospitality works. Visit Breezeway.io to learn more. And if you sign up in September 2026, Alex and any listeners will receive 20% off their first three months. Did you notice that?

Reviews, owner expectations, and the professionalization of the industry

Alex Husner 22:00

One point that it became easier to get property managers to understand the value of what you do when reviews became such a thing. And like, you know, the cut the guest, their their input was so much more valued than it was back in the day. I mean, I can only imagine that must have caught up. And then people were realizing, like, okay, this is where it all connects the dots.

Jeremy Gall 22:20

Yeah, I think guest reviews do. I think we've just seen that. I mean, COVID, whether it was this trend was happening pre-COVID, but I think it took a it took a few years. It didn't happen immediately in like 2000, you know, there's this like evolution of vacation rentals, um, which I alluded to a little bit before, which is like they were totally separate. Expedient TripAdvisor, you know, invest in Flipkey. They buy Flipkey, Airbnb buys hotel tonight, Xpedia goes and buys Verbo and Home Away. There's just more and more cross-shopping of vacation rentals and hotels. It didn't happen immediately, but that has had a progressive impact on changing guest expectations about how vacation rentals are serviced. The vacation rental you're in, Alex, looks nice from this view, and I'm sure it is, but like we've all sort of lived this in 2009. The standards were not nearly what they are today. You could walk into um a vacation home in South Carolina, and you'd probably expect that there'd be a palmetto bug, like um Yeah, there'd be crumbs on the counter.

Alex Husner 23:30

It's not a big deal. Yeah, and it was like, it was okay.

Jeremy Gall 23:32

You would almost like, I mean, I don't want to, I don't want to, you know, make it sound too harsh, but like you would almost expect as you're coming in, I better stop and make sure I've got paper towels and cleaner because I'm gonna clean up a little bit when I walk when I walk in the door. And that is wildly different than the expect than the expectations today.

Annie Holcombe 23:53

Yeah.

Alex Husner 23:54

These days, yeah, that's very true.

Annie Holcombe 23:55

I grew up vacationing between my best friend had um rental house in um Plymouth, Massachusetts, and Cape Cod. They they varied um over the years. They sold their places and so it was there. And then my family always went to the outer banks of North Carolina. So we always had to bring all of our cleaning, all of our linen, all of our towels, all our stuff. And it's so funny to me now to think about like you can go on vacation. And if somebody told me I had to bring all my stuff and be like, what's the point? You know, like why would you even go on vacation if you've got to do all this work? But you're right. I mean, when I was in property management, and thankfully at the time, when I was a property manager, most of the condominiums in Panama City Beach had been built like just in the last, you know, 10 years. I mean, they were all, well, I say five years, they were all relatively new. And so um that that we had we had shiny new product for a few years. And then as we grew our company, we started to pick up stuff that was built in like the late 70s, early 80s. And you know, there was stuff that still had like shag carpet and you know, brown bathrooms and stuff like that. So, you know, you definitely started to mix that in. I and I do think um that that guess expectation is definitely what kind of tipped the scales. But it was interesting. We were talking to Rachel all day this week and talking about kind of like building up owner trust. And she mentioned Breezeway as a way to be able, like, you know, so owners could reach out and be like, I don't

The growing importance of cleaners and third-party service providers

Annie Holcombe 25:11

know what you're doing with my property yet. Like, I haven't seen anything, or what are you doing to protect it? And she can pull all these reports and show like how many times people have been in the property, how many times people have been in to do service, maintenance, whatever. And so I think that you answered a trust issue that any property manager had prior to that, because they just could say, like, I could show you like a stack of tickets. I mean, here's like the tickets that have been put into each team, but obviously you can't send that to an owner, you know, broadly and communicate that. So I think just that ability to continue to build up trust with the owners is it is it it's worth its weight in gold and what you guys offer.

Jeremy Gall 25:45

Yeah, I think owners have become much more sophisticated too, right? I think they at the same time as this cross-shopping is happening, owners are questioning like what value am I getting? How much work are you doing? Why am I not doing this myself, you know, why am I not doing this myself? How hard could it be? There's been plenty of that over the years. But I think as the expectations increase for the guests, that's will only accrue benefits to property managers because it becomes I think it's it hasn't become impossible yet, but it will become very cl you know, become very, very difficult to be an accidental host and sort of mail it in and not do a really good job and not be a professional. You'll just you will get buried in the ratings and reviews. Um, and I think I think truly, Alex, like the ratings and reviews have helped, you know, the first the first bit of the game back even when Flipkey was starting is just like, how do we get everything online? How do we get it all online? It was emails. I remember conversations where people are like, there's no way people are gonna book online. They want to write, you know, it's absurd. Sounds totally crazy to say now. Like people want to write checks.

Alex Husner 26:59

That that was the name of the game back in those years. Yeah.

Jeremy Gall 27:03

Yeah. Shockingly, they don't want to write a check and go to the post office and mail it and follow up and make sure that they've reserved their vacation. They'd like some confirmation. But those review now, what's happening, you know, there's still the industry, I think, still faces uh quality. We still face a quality issue where everything's online, but there is real disparity in quality. And guest reviews are gonna help shake that out. But I think there's just gonna be a continued move to professionalization, higher standards, better operations, um, and more service. And it's not gonna go in the opposite direction.

Alex Husner 27:43

Yeah. I mean, I think reviews have always been a complicated part of the business, and they've taken different lanes of where what the reason is that they're complicated. But I remember when FlipKey launched, that was a big thing of like, oh gosh, wow, people are actually reviewing properties because nobody was asking for reviews back then. I mean, some companies were doing your Google business profile, but not a whole lot really focused on that. Um, but you know, the challenge is now with so many bookings coming from the OTAs that even if the direct website has a process to get the review, if they stay with them, you know, it you you can't ask somebody to review more than twice at the most, I would say. I mean, like you're lucky if you get it once. But it's like, I feel like that's become really a really broken part of the business that it it's it's almost like it's overwhelming to a guest, I feel like. And now that I'm staying in vacation rentals now more as I'm traveling uh lately, it it it really it's like you it's an overwhelming process. When you're getting review requests from different sources, it it just becomes kind of more burdensome. But um, does Brisbane play any part in the review process now? I mean, I know you're making it so that there's hopefully more five-star reviews, but is there any mitigation of where you're involved there?

Jeremy Gall 28:56

We partner with Riva to help on like guest review collection.

Could robots eventually handle vacation rental turnovers?

Jeremy Gall 29:01

Um, and I think that's a big part of it. And then we're doing more, so from the guest perspective, we leverage a great partnership with them. On the operational perspective, we're gathering more information, like whether the review came through Riva or otherwise, to pair that material with, I think there's a there's an increasing future around service provider engagement and how important the service personnel is to your business. When we surveyed our houses, you know, 90% of property managers rely on third-party service providers to get at least part of their work done. And I think that ecosystem is only gonna continue to grow and like labor is gonna become even more important. And so then matching and understanding the quality of that labor and your team and your extended team through service providers is gonna be critical. And then pulling in operational insights from those folks so that you can be even better at what you do is gonna be a big part of that's a big part of Bree Space future.

Alex Husner 30:00

Yeah. No, that makes a lot of sense. And I've got a follow-up question on that because somebody said it to me for a different purpose the other day that even if you're able to see the reviews of cleaners, in most cases, in most destinations, finding cleaners is already very hard. So what can you really do with the data? Was the question that somebody asked me of that. And I said, it's a good question, right? I mean, like you can try and coach the cleaners to be better or make a change, but when workforce comes into play, what do you do? What what would you say if you had gotten that question?

Jeremy Gall 30:32

Yeah, I think that um it's an area we are heavily focused on. We'll be announcing a couple of new things um over the next month or so. I think it's a blind spot, to be honest with you. Like and uh what you can do is the people who are really good, like variable compensation, I think is an increasingly big part of like the operational workflow for property managers, which is like, I'm gonna I'm gonna bonus you based on uh high quality reviews that are tied to cleaning, there's gonna be variable pay, piece rate's gonna be a little bit more flexible, you're gonna be rewarded. And this could turn into you know paying people a bit more and higher cleaning fees that get passed on to guests. But it's such a critical component. You know, if we all agree that like the standard of cleanliness and presentation that you expect when you walk into a vacation rental has gone up, like that doesn't come without a cost. And that cost, that cost to property managers needs to be needs to be managed a little more effectively. And so I expect the you know, the rate that cleaning and maintenance um costs is gonna go up, not down, and that it's gonna have to get passed on to the, it's gonna have to get passed on to the guests.

Annie Holcombe 31:47

That's always a struggle that managers deal with is paying that because it's such an important part of the business. And and it tends to always be the lower scale of, you know, your pay scale of your staff is is cleaners. And and I always wondered that. I know when I was a property manager, we did bonuses for, you know, for getting cleans done, doing the number of rooms, but it was really more about the turns. It wasn't the quality of it. So I think going back to the quality of it, but being able to have records of that is is is helpful. And I don't know, I think with some of the automation that's gonna come into play, some of the AI that's gonna come into play, there's gonna be some money that's freed up that think people could put towards really paying the staff. Um, because let's face it, I mean, cleaning, I've had to clean rooms before and it's just not fun. It's just it's not a fun thing. So it's it's um it's almost thankless work at this point.

Alex Husner 32:34

What do you think about robots, Jeremy? And the future of them being able to do the cleaning because I I feel like that's where, you know, none of us really have that crystal ball. You probably have a cleaner one than we do. But where do you think that's gonna go?

Jeremy Gall 32:46

I think I've actually been thinking about it. I think on the one hand, there's not a better industry for like, you know, robot cleaning, you know, there's high utilization, there's in you know, important turnover, and you know they're gonna get used and utilized. So if you had a fleet of robot cleaners and you have enough turnovers, they're gonna clean more frequently than they would in a residential or in a long-term rental context. So on the one hand, it's like, wow, this is interesting. This could be like the best use case. On the other, I just can't help but think that it's gonna be challenging for them to be as quick as a as as humans. And for a long for quite some time, it's just gonna be

How AI is changing vacation rental operations

Jeremy Gall 33:31

challenging to move around as quick as a human. And the turnovers require a certain sort of pace that I just don't see it happening like right away. Could have make sense in the long run, but I think it's gonna take a bit.

Alex Husner 33:45

We're gonna see robots like running into each other in the hallways and things.

Annie Holcombe 33:50

I just see robots falling down the stairs or getting like like or getting short circuited when cleaning a toilet. I don't know. It just there seems like there's so many things that could happen.

Jeremy Gall 33:59

Exactly. And you don't really want them in, you know. I think people are understandably concerned about their privacy when they're in a vacation rental. So they don't want those robots cleaning while they're there. So I just think there's like an operational burden. The turnover is so has to happen so quickly, and it's not the rooms are not or not fun, the homes aren't fungible, right? Like you need to stay in that house versus another house I might have, um, because that's the one you booked. So it'll probably happen in the hotel context faster if they can move people to a different room and it doesn't really matter. Uh piece isn't a problem. Yeah.

Annie Holcombe 34:35

It'd be interesting to see. Like if you check into a check into a home and you open up the the owner's closet, gets left unlocked, and there's a robot standing in there with your um I didn't actually want to go over to AI. I wanted to talk about you guys recently got an investment, I guess a strategic investment, um, and kind of talk us through that and and what that's what that's all about.

Jeremy Gall 34:59

Yeah, it's exciting. I think um, you know, we've capitalized the business for many years with external investors um to help us grow. And I think we've been uh pretty pragmatic and and thoughtful about that process. And then as we reached a larger scale this year, we felt like it was the right time for a more strategic investment from a growth-minded um private investor who could help us sort of make it to the next stage and and navigate the next four years of the business and how we continue to triple this business. So it's a great group out of Atlanta, resurgence technology partners. And I also think like we're at a scale of a business where there's a lot to be learned. It depends on the investors you pick, right? But if you pick appropriately, there's a lot of lessons to be learned about how you can be more effective, build a better business, think about how they become an extension of like what we do internally to um give us a lot more horsepower. Um, and capital, and capital to the business so that we can continue to invest.

Alex Husner 36:02

Yeah. And and honestly, I I think I don't know what weight you'd put on the capital or the people, but I I think the the people that you choose, and the way I've heard you describe it a lot as you just did, is that you know, that really means a lot. And you know, finding those right investors that are going to be the ones that really can take you to that next level. I mean, you guys know the industry, your team inside and out by now. So it's not like somebody needs to come in and teach you more about what you already know. It's how how do you grow the business, how do you scale it, how do you, you know, continue to improve the tech in ways or the team in ways that maybe you haven't thought about to this point. So I think that's a big part of it. But uh one question that I have. So it's been around for quite a while, uh, not as long as some of the you know older PMSs, but a lot of the, I wouldn't say your legacy at this point, but like a lot of the older that hasn't come about in the last you know, three or four years, the struggle that they have is more, you know, now how do they adapt AI into their technology? And do you feel like you guys just built it better from the start to be able to adapt and move things quicker over the years? Or are you also having to go through that same kind of rebuild of things so that you're ready for for the next chapter? And was that also part of the consideration for the investment?

Jeremy Gall 37:16

Yeah, awesome, awesome question. I don't feel like we have to do a rebuild. I know we don't have to do a rebuild. I think I wouldn't say we just built it better, but I think we were pretty disciplined about how we how we built. And I think that AI is a new tool to be able to leverage across the system to drive further automation. It's different than rules, but you know, Breeze Bay is built on, um, at least years ago when we first did it, is built on pretty sophisticated and heavy rules-based logic, which says, you need to do this, let's follow the rules down and let's build a predictable standard to your operation. But the data, but the insight that led to that was every property is unique, every property manager is unique, and they want to work to a certain brand standard. But we can't have all of these unique crazy fields. We have to have some data. We have to have some data structure to Breeze Bay, or else we won't be able to execute on these rules. So from the beginning, we had some tight data structure to everything that we knew about properties and about reservations and about your workflows and about your people. So we were in a good position to leverage that same data structure for AI tools that sit on top of that. Which is exactly which is exactly what we've done over the over the last couple of quarters. And I think that's important because I think property man, I mean, I know it's a grind. Um, and it's messy. It's very difficult to fully automate. Because you're dealing with so many humans and with so many exceptions and last minute changes, you have to be able, I believe my my take is that the ultimate solution can provide significant automation, can leverage AI to remove a lot of the administrative burden and speed, but that you have to be able to maintain the fallback functionality for someone to come in and say, like, actually, this is like AI can't solve this one. I need to assign this, I need to get deep into this. We I need to get deep into the weeds on this one, and I have to follow it all the way through. So my take is you still need that, you still need that structure and you still need all that functionality. You just need AI layered on top of it to drive a lot more, you know, real automation, not just not, hey, I want a different interface to to chat with, but like, you know, real value.

Sponsor Spotlight: Monarch Collective

Speaker 39:48

My name is Miller Hawkins. I'm the president and broker

Why Breezeway continues to go deeper on operations

Speaker 39:52

in charge of Boo Realty, as well as the Atlantic Resort Group. Both are under the Monarch Collective umbrella. I was asked several years ago while I was on the VRMA board of what my exit strategy is. Kind of hit me of, you know, I'm approaching 60 years old at the time and I'm not ready to retire now, but at some point I've got to have an exit strategy. I was introduced to the Monarch Collective a little over three years ago. I did not want to sell and give them the keys and leave. I wanted to stay on board for three, four, five years. And that's what their MO is. They don't want to buy a company from somebody and automatically go in and assume operations. They basically said from the get-go that when we do partner with a company, we work with you and support you in your current role as president to uh make life easier for you. We will support you and work alongside of you until the day comes when you do decide to leave. Before acquisition to after acquisition, as far as the brand, nothing has changed at all. The only thing they've done is support it. They brought in the resources, but they brought in, the support team, everything on the back end marketing, revenue management, financial, accounting, everything. They want to free up our time so we can grow our company, run our company like we've done without the burden of all the back office things. We have grown a number of owners. We have grown financially. The loyalty and the attitude with our owners, the attitude with our guests, the attitude with our employees has done nothing but go up. The advice I would give to a vacation rental owner who is remotely thinking about selling their business in the next five years. Don't wait until that time to start the conversation with the monarch collective. Reach out to them now. They have an acquisitions team that will fly to your location, they will meet with you, they will get to know your business. I strongly suggest you reach out to the Monarch Collective now. The best business decision I ever made was to buy Boo Realty back in 95. The second best decision I have ever made was to partner with the Monarch Collective the way we did.

Speaker 3 41:54

If you're curious about what the next chapter for your vacation rental business could look like, Monarch Collective offers a free, no pressure conversation to help you explore your options. No strings attached, just a straight conversation with people who deeply understand this industry. Visit gomonarch.com slash partnerships to learn more.

Annie Holcombe 42:14

In terms of like Breezeway's growth and penetration in the industry, um, I think it, and you correct me if I'm wrong, but it seems EB that you work with a certain size property manager, but theoretically this works for somebody that has one property all the way up to what, you know, tens of thousands of properties. What does your core customer look like right now? And where do you see, are you, do you see yourself being able to, I guess, if you're not already working with more of these individual hosts? I mean, we were talking about it before we got online. So many people are just, they don't have a PMS, they don't have a website. They're using their booking channel as their as their website. And you know, they might be using iCal or they might still be. I mean, I've talked to people in in Latin America that are still you doing everything handwritten on spreadsheets. So yeah, like what is what is the future, what does the future look like for Breezeway in terms of like getting broader broader um adoption within the industry?

Jeremy Gall 43:09

Yeah, I love that. Yeah, I think um we've got lots of, you know, we have clients with 20,000 units in Europe or you know, 5,000 units here in the United States, and we have really small ones. The average customer probably has about 45 units, which kind of matches the industry sort of average if you take everybody into consideration. Yeah, I'm bullish on the smaller segment, on this like SMB, much smaller, nimble property manager in the future of those folks because I think they will professionalize. I think they're at an early stage where software adoption is still low. There can be really good reasons for people who have just one property or two properties to have a PMS. I think a lot of that depends on am I managing just my homes or am I managing for somebody else? As soon as I'm managing for somebody else, I gotta worry about like a money flow and a calendar and what's my channel distribution strategy. Um, there's good reasons to have a PMS, even if you're really small. And then depending on your goals, there's some reasons where you really don't need one. But either way, operational efficiency and excellence, like again, not for everybody. There's plenty of folks who signing tasks through the PMS and getting that work done is good enough for what they wanna, it's good enough for what they want to accomplish. And they can run their business that way. And they're making there's trade-offs in everything, and they're making a a decision that like simplicity in their tech stack is beneficial to them and makes their life easier, potentially, you know, instead of some optimization or something else that they gain by looking at separate revenue management and and separate tools. And so it's not going to be for everyone, but I think, you know, we started as an operations system. We turned more into an operations platform by thinking about communication and how actually the operations drives the guest experience and that it's the most important part of the guest experience. And I think the next, the next evolution of Breezeway is like this is where the hard work of hospitality happens. Like this is where this is where hospitality works, where the service professionals, where the work gets done. It's a different mandate than the BMS, but every but it applies whether you have 50 units, you have 500, or you have five, and you're trying to coordinate that work and make sure it gets done because you're not there and it's happening remotely.

Alex Husner 45:40

Yeah, makes sense. And I I've heard many people say this over the years. Some sure this won't be the first time you've heard it, but why, since you have customers that love you, you know the industry very, very well. How come you guys haven't ever just decided, well, we could build out the rest of the stuff and we could just be the PMS? Because you have probably the hardest part of it nailed down, like figured out, right? Yeah. Yeah.

Jeremy Gall 46:05

That's a loaded question. That's a loaded question. The um I the the honest the honest truth is that um, you know, I do this because I am pretty obsessed with um it feels really good to deliver value to clients. Like that's what gets me, that's like what gets me going. And I think that's probably how we've built loyalty with customers. And we try really hard. And I try really hard to do that. And I just feel like there's still a lot more to be done on the operations. I just feel like there's still a tremendous amount more that we can do to help people improve their operations and deliver better experiences to their owners and guests and like and to their staff and just like build better businesses. It feels premature to give that up to start thinking about a PMS solution where there's a robust market of PMS solutions, like, and people have good solutions that they can work with to fulfill that functionality. And I'm not sure us doing that, even if even if we could and people loved us and wanted us to do it. I just don't know if that delivers differentiated value to clients. It really like moves the needle as much as like if I dedicate our resources to going, you know, much, much deeper through AI and through other pieces that we're pulling in and through a focus on your people and the work that's getting done, we can change your business, I think, more dramatically by continuing to do what we do.

Annie Holcombe 47:35

Yeah, I would agree with that. Everybody that I know that uses you is a raving fan. And I I have to say it's very rare that you can find software that across the board people just like and really enjoy using and and would recommend wholeheartedly. I mean, I think it's you'll find detractors on, but I have to say I've I've not really ever heard anybody have any issue and they just feel like you do pay attention to what their what their business is. But you kind of alluded to you've got some things um that are coming. Is there anything that you can share with us that uh the audience would be interested in that you've got developing or coming out maybe before VRMA that they'll want to take a look at?

Jeremy Gall 48:14

Oh yeah. There'll be a there, we've got um several product announcements that are going to come out before VRMA. We've been working very diligently in the background to add a layer of intelligence into your operations such that we know I think we're approaching about 100 million tasks that have been completed through Breeze Bay over hundreds of thousands of unit, you know, properties over this time period. So we've got like just a lot of insight.

Alex Husner 48:43

Tons of data. Yeah.

Jeremy Gall 48:45

Tons of data. Yeah, we have tons of data about like how operations are done and how it's done well and what operators have learned and the pattern recognition of like what's about to go wrong and the last minute things that operators have to deal with at 6 a.m. on a Saturday when somebody calls in sick and like what happens next, and what's the cascading amount of work and administrative hassle that a manager has to face? And in the background, we've been building a great tool to take that on and to sit basically on top of Breeze Bay and become that automated operations controller to really change the workflow for clients. And so we'll have that announced shortly, um, which is one of the big sort of AI initiatives that we've had going in the background. So we're very excited about that. And then another initiative, which I alluded to, which is really like focusing on the people who are getting work done in the field in a number of ways, like and making sure that Breezeway is the preferred platform to understand how that work is performed, get paid for that work, find more work through a network, um, through a network marketplace, embedded, do better training so that you know who knows how to do what. We've long been doing that with Justin Ford on the safety side of the house. Um, and now we're taking the opportunity to embed a lot of that training and industry knowledge within Breeze Bay so that people can use that. We know that that's a problem. People have staff that starts every year training and getting their teams, internal and external, up to speed on their brand standards and how they work is a hard thing. And we have great like task management and all these checklists and all the raw materials to be a great like training center for people. And so that's coming out as well.

Alex Husner 50:36

That's exciting. What what are you talking about? The uh the ability to anticipate. I think that's really the difference between operators that are to that next level versus ones that are either just getting into it or just you know, still trying to kind of operate by the seat of their pants in a way. And that makes a huge difference, you know, being able to understand problems before they're gonna come. And with what AI is doing and what what you guys have of your knowledge of this industry, I think is gonna be really powerful. So we're excited to see all that. And I'm sure you guys are gonna have a whole parade at BRMA this fall.

Jeremy Gall 51:10

We we we will indeed. There'll be a lot of good students. Um, I hope you're there recording on site.

Alex Husner 51:16

Um, yeah, we'll be there, hopefully.

Jeremy Gall 51:20

Um we can talk about it again. Yeah.

Annie Holcombe 51:22

Um, so just for inquiring minds, pickleball tournament, you'd be playing in that this year.

Jeremy Gall 51:28

Our inquiring minds want to know. The uh they want to know.

Annie Holcombe 51:31

They want to know.

Jeremy Gall 51:33

I'll show up for some pickleball this year. Yeah.

Annie Holcombe 51:37

I feel like between you and Robin Cragan. And well, Sarah is not Sarah Bravo's not as much around anymore, but like you guys are like the pickleball people. Like I just always know that wherever there's a pickleball tournament, you're gonna be.

Jeremy Gall 51:47

Let's get some nuts and some exercise while you go to these things.

Alex Husner 51:51

Yeah, definitely much needed. So true. Yeah. Awesome. Well, Jeremy, it was a pleasure to to finally have you on, the man himself, and and we're just excited to watch and see where things go with Breezeway. And uh, we love your team, and you guys have been great to work with. So um, if anybody wants to get in touch before VRMA, or if they're not going to VRMA, what's the best way for them to reach out to you?

Jeremy Gall 52:14

Yeah, they can shoot me an email. Um, I love to connect with folks in the industry. It's just Jeremiah at breezeway.io. And for listeners, you know, who are, we'd love to have folks who want to join Breezeway or new clients interested in what we're doing to get a special promotion if they sign up in September and get 20% off for the first three months. Um, nice. Reach out and take advantage of that. But you know, be in touch. We'd love to learn whether it's to talk about how Breezeway can be helpful or truly to talk about your operations and what we can learn from you. Awesome.

Alex Husner 52:51

Well, if anybody wants to get in touch with Annie and I, you can go to alexandannie.com. And until next time, thanks everybody.