From 1 Property to 100+: Inside the PMS Powering 62,000 Rentals

AI is one of the biggest trends in the industry right now. And this is one of my favorite topics because it's often where property managers see the fastest return on their investment. There's not one property management software that's right for every single property manager. We're at the tip of the iceberg in this industry, but you're definitely seeing the guest expectation increase. And travelers want hotel-like amenities. They want that fast, accurate, seamless communication. And automation helps property managers just deliver that consistently and constantly whether they're managing

five properties or 500 properties. The goal is simple, Tim. It's we want to just help property managers deliver this five-star experience. We don't outsource. We don't third party. Again, that's why we have a 97.1 CET. Welcome back to the Short-Term Mental Riches podcast. I'm happy you're here again and I'm happy again to be seated virtually with another leader in the industry. Today we're with Frank Bosi. He's with Hostfully. He is their senior director of partner development. He's been with them for years. He's been with their

journey as Hostfully has grown to now help us hosts out in the industry manage tens of thousands of properties. So excited to dive into the details today, Frank. Welcome to the show. Yeah, thanks for having me, Tim. I'm really excited about this. It's a long time coming. This industry is just changing so quickly. You know, I one of the things that is changing quicker than most things is the technology. I know Hostfully's been right there. I remember actually years ago, Frank, like long time ago, like

over a decade. I was in Canada at a conference and I was in this breakout room. I was listening to this incredible idea to have a digital guide book for our guests. I mean, this was way back in the days, right? That person giving that breakout session was the founder of your guys's company today. And you guys have just come leaps and bounds from that day. And so, would you mind just just sharing with the audience a little about yourself and a little bit of background

about Hostfully? Yeah, I mean, a little bit about myself so we can get that out of the way. Prior to Hostfully, I was in the luxury hospitality world. When you were at that conference, I was working the front desk, working the sales team. And you know, I spent years working in hotels, really just focused on sales, business development, and just building relationships specifically with our guests because they were highlevel, hightouch, luxury, hospitality folks. What I've really always loved about the hospitality industry is that it's ultimately

a people's business. you know, whether you're creating like guest experience or growing partnerships, which is kind of full circle, but I remember watching the short-term rental industry for years, even at conferences. Airbnb would be at the hotel conferences that I would attend. It was just so innovative on how Airbnb was they were changing how people traveled. You know, they changed how operators were becoming more sophisticated and technology like a guide book 10 years ago. It was transforming the space and I was fascinated by it. But

I never made the jump because I was doing so well in my hotel career. But then co happened, right? So like many people in the hospitality industry, I was laid off when travel just literally came to an abrupt standstill and that time it felt like a step back. But like looking back now, it ended up being one of one of the best things that could have happened to my career because that's when I found Hostfully. And I entered the short-term rental industry full-time six years ago.

And again, I've been with Hostully for six years. So, kind of do the math. It was the first company I came into in the short-term rental industry, and I've been here since. And the best thing and what surprised me the most specifically in this industry, and you touched on it earlier with uh your presence at the conference and talking about guide books and how new it was, it's how innovative and entrepreneurial that this industry is. You know, like operators are just they're constantly testing new ideas.

They're adopting new technology and they're just finding out of the box ways to grow. They're much more strategic. And the deeper that I've gotten into this industry, obviously, the more I learned, but it's also the more excited that I've become, you know, and and AI revenue, direct booking, smart home technology. It's so much more than just vacation rentals, which is what I thought about when I initially started. And what drew me to Hostfully and this opportunity and what keeps me here 6 years later is that

this industry is just full of incredible people, entrepreneurial u mindsets and it just feels like we're still in the early stages of what's possible for this industry. So it's that excitement of the c like just the consistent innovation that's happening. Yeah, I totally agree. You know, it's exciting that now, you know, technology is is just leaps and bounds ahead of where it was. For maybe the the few people in our audience that haven't heard of Hostfully, uh most people, I'm sure, have. Can you give us

just the the highle view of what Hostully helps hosts achieve? Yeah, and that's uh that's kind of my job at high level, you know, like my job is all about building relationships and help hostfully grow while still creating this value for property managers. across the industry and again working with sales and marketing and our leadership teams to find new ways to increase our visibility. Uh we want to generate more opportunities and leads for our sales team and we want to just strengthen our position in the

market overall. So for those of you that are not familiar with Hostfully, my sales pitch is we're a property management platform specifically built for uh short-term rentals and vacation rental operators. But what excites me the most is how quickly Hostfully is evolving. Kind of going back quickly is one of the reasons I joined Hostfully and why I stayed is our commitment to innovation. With Hostfully, we've launched Hostfully devices recently. We obviously have our property management software and our digital guide books. But with Hostfully devices, it's

one of our newest features and capabilities, and it's ultimately to automate your smart home operations. We're enhancing our accounting capabilities. We now have a new feature or more like a product at this point and we've introduced it a few weeks ago and it's uh hostfully screen and protect and that ultimately helps operators reduce risk and just protect their properties. So just touching on the innovation we're more than just a property management software at this point but at the same time hostfully is continuing to strengthen the

core platform. So, we help property managers synchronize their rates, their calendars, their reservations across Airbnb, Burbo, Booking.com. We have Google Vacation Rentals, Homes and Villas by Marriott International. We integrate with a lot of different channels, especially the niche ones that are specific to your market or that individual's property, that property manager's uh market. But we also automate guest communication. We power direct booking websites, but ultimately we're here to streamline your day-to-day operations and help you scale and grow comfortably. You know, not we don't want to

overwhelm you. We don't want this difficult software to learn hostfully is very user friendly. And honestly, what what kind of ties everything together is our culture and it comes down from leadership and our CEO. you know, we listen closely to our customers and many I if not all of our innovations come directly from their feedback. So when people ask me like what's Hostry, I usually say that we're more than a property management software. Um what we are is we're a technology partner. We're ultimately here to

help property managers grow, scale, automate, and just build their businesses with with enjoyment and confidence at the same time. So, little bit of a tangent, but that's hostile, you know. Yeah. No, that's that's a great overview and I think the way you phrased it is probably more accurate today, a technology partner because a lot of the things that you mentioned are things that, you know, our team lives every day and we hear out there in the in the world that are challenging. you know, there are

operational pieces that could be easier, but the perfect solution doesn't exist yet. Software is a lot easier to create than than it ever has been, but that also kind of makes it challenging, too, you know, because there are so many pieces of the short-term operation. You mentioned you guys take all of your customer feedback uh very seriously and that leads the product, I would imagine. Let's see. So, you mentioned smart home locks. You mentioned direct booking, you mentioned pricing, you have the guide books, of course,

you have the property management software functions. Can you shed a little bit of light, Frank? Like, how does a software company like Hostaly manage all of those different new products like effectively and make sure that they're stable and and strong and a good fit in the market? Yeah. And again, I I don't have to deal with all of that. Our leadership team does an incredible job with all of that. And even just our, you know, we're just our culture and our environment. It's industry knowledge, I

guess, at this point where Hostfully is one of the leading property management softwares in the industry. And it is because of our team. We work very well together from billing to development to sales to customer service to support to onboarding. Like we have this just just this incredible environment in which we're open, we're transparent, we're honest in order to make all of these new features and capabilities work. And the great thing with Hostfully is we will not release something that is not one at that point.

Like we have a lot of features and capabilities that are on our road map which in the next couple of months it's going to be really exciting. So keep your ears peeled and keep your eyes open uh cuz we have a lot of really cool things happening in the industry. But the best part with Hostal is we won't release something that's not ready to be enjoyed and used by our customers. kind of keeping everything together, I would say is is the people and our relationships with

each other is just it's it's one of the best cultures that I've ever experienced and it's industry known that Hostfully has one of the best um cultures, but also customer success. I mean, we have a customer success score of 97.1%. So, our customers are really happy with us and that's because of our response time. Um, but also going back to innovations and having all of these new features and products come out is we're doing it strategically, but we're also doing it based on the feedback from

our customers. Now, do we get a lot of it'll be great if you have a dynamic pricing included or built into your software? Yeah, it will. But we're not there yet. We have a lot of other features that our customers have been asking for and a lot of more a lot of improvements. We're focused on that. It'll be great to have direct booking options. Is it coming? possibly. I have no idea. But it's really taking the customer need and what they need from our software first

and then we can add those bells and whistles later on. So, it's kind of just being a little bit more strategic with what we offer. Cuz again, like you mentioned, Tim is there's there's not one property management software that's right for every single property manager. And I say these on all the podcasts, webinars, interviews that I speak on is like you need to find the property management software that fits you and your operations the best. And then that's the property management software you will use. And

but there are a lot of property management softwares that will sometimes jump the gun and kind of put the cart before the horse in many ways where those new products and features aren't there yet, but they're just they're just releasing those just to kind of get more visibility for the property management software in all. Check the box. Just Yeah, exactly. Check the box. where with us, you know, there are a lot of products and features that our competitors have, but it's still making Hostfully one of

the top property management softwares in the industry because of that is that we're not we're not putting the cart before the horse. We're taking our customers needs first and we're going from there. Ah, gotcha. Gotcha. Well, what would you who would you say, Frank, like is your ideal customer at Hostfully? Uh, you know, is it like the individual operator? Is it someone with a few units? Is it someone with a property management company? Or or is all of those? D all of those. All of the

above. Yeah. And I one of the things I love about Hostfully is that there isn't like there's not one specific type of customer that's the perfect fit. Hostfully is built for operators who are serious about growing. So, if you're serious about growing, becoming more efficient, and just creating a professional guest experience, regardless of where you as a property management, a property manager are in your journey, Hostfully is the software for you. I mean, we work with hosts managing one listing. who are ready to move beyond

spreadsheets and those manual processes that a lot of them are used to. But we also work with growing operators, you know, managing 10, 30, 70, a thousand listings who need better systems to keep up with their growth. D is the answer. Okay. All right. Well, one of the the features you mentioned that I'd like to pick your brain a little bit about is accounting. Um, I think one of the things that's changed a lot over the last years in the short-term rental space is the accounting.

Um, I haven't found perfect systems in the property management software, you know, solutions that I've used over the path in the past. And there's also quite a few different ways to do accounting now, like if you're a property manager, there's trust accounting, but if you're an individual owner, like you just need to know how much your property is making, and there's a lot of pieces to it. Can can you tell us a little bit about your guys's account uh features? Yeah, I think um I think

we can definitely improve there and we've added so much more. We have enhanced reporting, but I think it the accounting module that we have and I think every accounting module touching on your point in property management systems can improve. So, we're working to just to constantly grow that specific request because a lot of property managers in general just need better accounting. We integrate with QuickBooks. We partner and and integrate with clearing which is one of the the leading software for accounting and just kind of seeing

what they're doing and having that as part of hostfully. So even with hostfully we integrate with over 120 software. So normally with accounting we focus heavily on our API our open API the seamless the seamlessness to communicate between the accounting software and hostfully. So there's a lot happening there in terms of the integration of accounting which is kind of what I would push towards because like dynamic pricing cleaning turnover accounting like they're specializing in that software whereas hostfully we're all over the place in terms of

property management you know we have the automated communication uh the the channel synchronization we want to give 110% to focus on accounting but we have a lot of other features and capabilities to work on so sometimes I always recommend And depending where you are in your operations, accounting obviously is super important and like I mentioned earlier, that's something that we're working on and we're really excited. We have a lot of advancements in our road map, our top of our road map that will be released soon.

We actually have a great team specifically focused on accounting because this guy, you don't want hingu or selling you accounting. That's not my forte. However, we have great people on our team that will assist you with that. And I think again just going back, it's that it's that strong partnership and integration with accounting software that will help you do that. Well, let's see if if you had to pick like the top feature, Frank, you think that sets Hostfully apart from some of the other solutions out

there? I know there there's a whole bunch of things that you guys are doing, a whole bunch of services out there, but what would you say that you guys are sort of leading the pack in if you had to choose one one area or feature? Overall, I think it's just our UI. I mean, our interface is so userfriendly. The channel synchronization, you know, we're preferred elite with Airbnb, Verbbo, Booking.com, Homes and Villas by Marriott Bonvoy. We have a lot of channel synchronization, Google Vacation Rentals, and

a bunch of other channels that are niche and specific to your market. So, I would say it's the channel synchronization that is definitely a forte for Hostfully. So, it's just the overall processes that we put in place. Again, I think a lot of it and what draws a lot of people to Hostfully are, yes, our features, our capabilities. We help out a lot with direct bookings. Our software is built to make direct bookings easier. So, our calendar is phenomenal. You know, it's pretty to look at.

Every channel has a designated color. It's easy to read. You can toggle on each reservation for a quick uh highle overview of that reservation. you can simply click on that reservation to get all of the stay details, the invoice, the rental agreement, the preferences of the guest all in one reservation. So just again using those features and capabilities and it's again having property managers with one listing and then having property management companies with 100 plus listings. They're looking for something different and the great thing is

that Hostfully can accommodate each of that. you know, it's there's not one specific, but I would say that channel synchronization, our calendar, our pipeline is unique to the industry. If anyone wants to learn more about it, please let me know. I'm more than happy to walk you through a demo in a meeting to get kind of granular on what we offer because that alone can turn this podcast into about an hour. But overall, I think especially with Hostfully in ways to stand out and how we

capture leads and interests and ultimate Hostfully users is our innovation, our flexibility to work with you, our ecosystem where we integrate with all of these different software. And then of course, you know, just bringing it back to our people because our people and our team is who is going to help you learn our software and all of the ins and outs, the workarounds, the all of those detail that you need specific to you and your company. Um, and what's important to you and our team will

help you find that within our software. Maybe we could expand on that a little bit because that is one of the challenges with software that starts to handle more and more pieces of the puzzle. there's more things to kind of figure out and you know having a great UI is is a good starting place but what does hostfully do or how does support work with hostfully you know for a for a new partner or a new uh customer joining for example again just like going back

to Hostel's innovation and adding all of these features and capabilities we have to learn it first in order to sell it but then once we sell it that property manager is on board and they're learning it themselves as well especially with our constant evolution. I mean again again the you know like the last year alone hostly devices expanding our accounting capabilities screen and protect continued investment in in AI and automation. We listen closely obviously to our customers and we're building solutions that solve these real world

challenges but as mentioned every property manager operates differently right so whether you're managing five properties one property 500 properties our team gives you the freedom to build workflows specific to your tech stack and specific to your business not the other way around and our ecosystem you know we have one of the strongest partner networks in the industry and a really robust that connects our customers with the best-in-class solutions across, you know, revenue management, dynamic pricing, accounting, guest experience, smart home technology, all all of those software

that are now in this industry. But going back to what you asked is our biggest differentiator is our people. So with Hostfilly specifically, every customer is assigned a dedicated onboarding manager and they will receive personalized one- on-one onboarding sessions. It goes from two sessions really. We we break it out in tiers depending on how many listings you have. But our onboarding team will not allow you to go live until you're ready. So we don't really guarantee a certain amount of one-on-one personalized onboarding sessions, but we

do also offer live onboarding office hours. So those happen Monday through Friday, 1 hour per day. And it gives our customers direct access to experts as they get up and running. So you're not just limited to those two, three, four onboarding sessions. If you have time during the week and you have we give you the schedule, you block those on your calendar. Yes, it's easier if you don't have a full-time job, but again, we're a global company, so those office hours range from EST to PST

and some as well as international for our international customers. The best thing about that is the success of those onboarding sessions led us to expand office hours to our customer success as well. So once you finish your onboarding, we don't just leave you to the walls. You know, we're not like, "All right, you know it, you're good to go." We have customer success team as well. So customers have an assigned customer success manager and they have access to regular CSM, customer success manager office hours throughout

the week. So, similar to onboarding, Monday through Friday, one hour per day for your entire life with Hostfully, you will have a day where you can talk to a real life customer success manager. And that's just in addition to our 24-hour, 7-day a week customer support and a team that's just so invested in helping that property manager grow long after onboarding is complete. So again, just the combination of like the innovative technology, the hands-on support, that's a big reason that we're proud to maintain that 97.1%

customer satisfaction score. Gotcha. Gotcha. Okay. So when someone starts with Hostfully, uh they have some dedicated onboarding sessions that depends maybe on how big the portfolio is or you know maybe the the new customers questions, but then after that they get assigned a customer an account manager basically. Yep. That they can join weekly at specific office hours. And then on top of that, there are also group office hours that someone can join it. So, lots of lots of support options. Exactly. Yep. And even with our

uh 24-hour, 7-day a week customer support. All of our support team, our customer success reps, everyone are Hostfully associates. We don't outsource. We don't third party. like they have our clients and hostfullies best interest at heart when insisting customers if you need help you're going to get it you know and that again that's why we have a 97.1 cesat I I'd love to pick your brain if if you might be able to share a couple notes on you know where you guys are using AI and

where you plan on incorporating AI in the future into the software. Yeah. So, uh, I don't know if you heard, but AI is one of the one of the biggest trends in the industry right now. It's with guest communication and the automation overall. And this is one of my favorite topics because it's often where property managers see the fastest return on their investment. You know, when you think about like the guest's journey overall, guests need booking confirmations, they need check-in instructions, they need their Wi-Fi details,

the recommendations during their stay. Um, but also what's important is the follow-up communication after checkout. Managing all of that manually gets extremely overwhelming very quickly. And this is where Hostfully shines. You know, like our automated templates and triggers really allow property managers to send the right messages at the right time. And you can get really granular as to when you send those messages before the stay ends, after the stay ends, before the stay starts, after the stay starts, on a specific day of the week. So,

you know, whether it's a booking confirmation, a payment reminder, a rental agreement. We even have uh really cool communication around upsell offers. You can also review uh you can uh request reviews automatically. That all happens automatically based on where the guest is in their journey, of course. Um but we also centralize communication through our unified inbox. So, we're bringing messages from Airbnb, Verbbo, Booking.com, text message, WhatsApp, email from direct bookings, and that's all in one place. So the property manager as well as their teams just

aren't jumping between multiple systems. The unified inbox has been a a great addition to the to our software. What I always tell people, you know, automation AI, it's not about removing the human touch. It's about removing that repetitive touch. When software handles like this routine communication, you and your team can now focus on delivering what we've all why we all started in this industry in the first place is for great hospitality. Uh that's where it matters most. And really going back to the beginning of this

podcast, it was that experience I have in the hotel industry and recognizing the hospitality and how important it is in the short-term world, especially because we are competing with hotels. Getting and delivering that great hospitality is where it matters most. And having all of these automations in place will make it a lot easier to execute that hospitality touch cuz also, you know, guest expectations, they're continuing to rise. We're at the tip of the iceberg in this industry, but we've definitely seen the guest expectation increase. And

travelers want hotel-like amenities. They want that fast, accurate, seamless communication. And automation helps property managers just deliver that consistently and constantly whether you know they're managing five properties or 500 properties. And again, tip of the iceberg, that's the really exciting part is we're just getting started. You know that we've already introduced AI powered capabilities and we have even more innovations on the horizon that will make guest communication so much more smart, more personalized and more efficient. So we do have that on the road map as

well uh which we're excited to share in the coming months. But at the end of the day, you know, the goal is simple, Tim. It's we want to just help property managers deliver this fivestar experience while spending less time buried in these like repetitive tasks that we can really leverage AI and and take those manual processes and put them to the side. For sure. Well, there's a reason, you know, tens of thousands of owners, investors, managers are using Hostfully, and you touched on a lot of

things there, uh, Frank. Yeah. And there's a lot of software out there as well that we integrate with that specifically focus on guest communication and automating that. So, um, we partner really well with a lot of integrations that do that again because of our strong open API. Yeah, I think that's really important to have an open API these days. Oh, yeah. and a good team to work with. That that's that takes the cake. Yeah. Yeah. Absolutely. Well, where if someone's interested in checking out Hostfully, finding

out more, what's the best way to do that? I mean, definitely hostfully.com. You go on there, you're able to review our entire offerings on our website. If you want a personalized demo, I'm more than happy to give that to you and tailor it around your specific needs. You can email me at frankhostfully.com or maybe Tim, I could send you my calendar and we can include that in like the show notes or in any communication and that'll go directly to my availability uh so you can book

a one-on-one demo with me. Mhm. Awesome. Yeah, I know there's there's way more to a PMS program that we can uncover in a short little episode, but thanks for coming on, Frank. I know that gives uh our audience a better overview of Hostfully and some of the guys some of the things you guys are leading the pack with and yeah, looking forward to to seeing the new updates as you guys evolve and expand. Yeah. Yeah, absolutely. And we're excited to share them. We'll we'll make sure

uh to get your details in there and thanks for joining us.