Setting Honest Expectations with Vacation Rental Homeowners with Kimberly Layton of SkyRun

For me is the property manager. That's visions and who I use to market through still needs to remain what I control because I'm the one with the contract with the owner. So I'm trying to figure out how do you navigate that you need all these different OTAs but still remain in control of the trust with your owner, the trust with the guest, and make money because it seems like everybody's just piling on with taking the money down to the bottom of the barrel and that's not sustainable for the the industry. Welcome to the Vacation Rental Show. This is your essential playbook to grow and scale your vacation rental business with advice and insights from the best in the biz. I'm your host, Lynnell Gordon. Welcome to the Vacation Rental Show. I'm Linnell Gordon, your host and I AM in Washington, D.C. today. If you can see the Capitol building behind me. And I'm very excited to talk to you about what enterprise technology might have to do with vacation rentals. I think it's more than you might think. My guest today has spent years in boardrooms, training and assisting Fortune 500 companies in healthcare, finance, retail to cut through all the noise and to align their strategy with their results. And now she's applying the same strategy, that same discipline to vacation rental property management. And the results speak for themselves. Kimberly Layton is the owner of Sky Run Vacation Rentals. And today we're going to get into one of the topics that I think separates good property managers from great ones. And that's how to set expectations with your homeowners and have hard conversations and to build relationships with trust that actually last. Kimberly, welcome to the Vacation Rental Show. Thank you. So let's talk a little bit about something. I was really interested in. Sky Run. I have actually stayed with Sky Run. I stayed with Sky Run in Colorado back in 2021, before they were a franchise and now they're a franchise. Do you want to help people understand what are the challenges, the special challenges you have in setting up a franchise? Because you did that from scratch. So yes and no. I own Sky Run Naples specifically. I bought the franchise after coming out of Dell Technologies. And the powerful piece about being a part of a three franchise is that you have the corporate support. What do I mean by that? You've got the technology stack, you've got the integration capability. Because running a business, running a franchise, having to know how to deal with the money part of it, how to pay taxes, how to make a listing, how to integrate that to Airbnb, vrbo, et cetera, et Cetera is no easy undertaking for an individual. And when you have a bank background of people, breadth and depth on the bench to help you do that, it makes the ability for you to go out and do what you need to do, which is acquire owners and acquire guests to actually make money for yourself and the owner. So that franchise piece out of Colorado where corporate is, has been fabulous. That's exciting. That is wonderful to hear. What is the one piece of advice you would give to people coming out of, maybe out of the corporate world into property management who are going to go into a franchise? What's the one piece of advice you'd give to them? Figure out, is it the right franchise for you? I hired a coach to actually help me figure out what I was best at, what I was not good at, and then to marry my capabilities to the right franchise because I looked at four or five different ones. But sky run from a property management and vacation rental business just was the right one. That's excellent. Let's get a little bit more into some of your background that you used in corporate America that you brought over into property management. Let's talk about setting clear expectations with homeowners. Tell me, how do you do that and do you believe like I do that it is critical to the long term success of this relationship? Yeah. So my success in corporate America was because I was just real. I just told a story. I took a product that I was selling, I told the value proposition of what that product was going to derive for the business leaders. I never sold on price because price is one thing, but the value that you add for sustainability, scalability is really what matters. And that's translated tenfold into how I actually go and acquire an owner, sell an owner, how I tell the story and make it real for them. That's in their language. What do you think are some of the biggest communication mistakes that property managers make when they're onboarding new homeowners? I think setting false realities in terms of what the revenue numbers are going to be. Covid era, especially in Florida, was very different from a revenue perspective than it is today. The Naples market specifically grew from a small group of rentals to a very large group. So with that becomes saturation and helping an owner understand that it's a seasonality down there. What those windows are, what you can get during season as compared to off season, how you're going to fill the gaps with different marketing strategies, how you're going to market with different avenues to pursue to get those rentals in place. Because it's the off season can be super tough in Naples. But back to your original question. You've got to be super honest with those owners. You've got to set those expectations, even if they don't want to hear them. So how would you balance honesty and transparency when it comes to market conditions? It's kind of hard to explain to a new homeowner, especially that market conditions make up so much of how much you're going to make. So how do you handle that? I'm dishonest with them. I communicate regularly. Most owners trust me now. It takes a little bit because everybody thinks their home is a payless. Everybody thinks that they should be getting $1,000 a night. Reality is, that's not reality. So I am just honest. Honest. I show them data from the tools that I utilize. So it's factually based, it's graphical. And I try to adjust my conversations to how they listen, how they learn. You gotta be straight to the point, get to it. Because most people listen to paragraphs of information. That's true. That's true. In your experience, what helps build lasting trust between property managers and their homeowners? Other than honesty, of course that's going to build trust. But what other things do you do to help build trust? I think it's how you handle things in the tough moments. So somebody's going to make a mistake. I've made a mistake with a percentile and a payout to a specific owner. I didn't catch it. We were doing a system transformation. When they caught it, I was embarrassed, number one. But I immediately picked up the phone. I didn't email, I didn't text. I said, I'm very sorry. I will course correct this right now. You will have money in your bank once I confirm it with my accountant that it's accurate. And I did it. I did what I said I was going to do. And there's other times when there's damage done to a property by a goofy guest. It's how you handle getting the claim put in, that you handle it like you said you would in your contract. And you basically go back to, I'm going to do what I said I'm going to do. And that just continues, I think. Great trust. How proactive are you in your communication with your homeowners? Every owner is a little different. I text with them. I asked, number one, how would you like to be communicated with? Because a lot of these owners are. They're being corporate executives or they're just busy with kids, whatever they are. So I said, do you want me to text you? Do you want me to email you? Do you want me to WhatsApp you? I can go on and on about the different ways your background includes enterprise technology and like strategic business solutions. How has that experience influenced the way that you approach vacation rentals? And is there anything that you can share with property managers that might help them? Yes. So the technology stack, as they put it. And so the way I look at it is you as an owner of a property management team have got to figure out where are my challenges, why are they a challenge? And is there a piece of software that I can invest in, pay monthly subscription to in the cloud that helps me with my housekeeping, my productivity, that allows me just to make myself more efficient because in the end you're trying to make money, you're trying to be profitable as quickly as you can while also taking care of your owners and your guests. So it's about always keeping up with what's new. Like I'll go to conferences or Sky Run will bring in fabulous speakers to our own annual meetings and educate us on here's how you could do it different, here's why they're better, here's their value proposition, here's the return on the investment you can get. Those are the same tools I used in corporate America and I have to take a step back every once in a while and I try to do it monthly to say what am I doing that's not working? And if it's not, let's pivot, let's figure out something to go to versus you know the adage of keep on doing it the same way you're never going to get any better at what you're doing. So I'm very open minded about pivoting if I need to. Are you leveraging AI? Yes, we are starting to. Isn't everybody? But you got to understand what it is first and you've got to figure out what. Can you ask that AI tool that would take you hours to research? Can't you just ask it a question to derive what it is you need help with? And so instead of hiring people, I've been able to use AI tools just to help me do it better, quicker and it really works and it's accurate. Interested in a unique franchise opportunity? Itrip Vacations provides a unique business opportunity in a thriving industry. Itrip offers an executive level income potential with a work life balance in an exclusive territory. As an itrip franchisee, you'll provide a full array of short term rental property management services for the properties that you manage. Itrip offers extensive support and training requiring no previous experience. Visit us online@itripfranchise.com to learn more. What got you in the vacation rental space to start with? Well, I researched a bunch of different franchises. I won't tell you what they were because some of them were kind of goofy, but I had, literally, we had a cottage in upstate New York that I would rent out three weeks out of the year just to help us pay the taxes. And I like taking care of people. I like fixing the dock when it broke. I liked making sure those guests had the significance. Incredible experience. And it wasn't automated. It was just me. Word of mouth in a newspaper ad. But I really enjoyed it. And for me, right now, when I retired, I wasn't even 60 yet and I needed something to do. I needed something where I used my brain, use my sales skills, use my. I'm an operational girl too, with organization. And my husband was still working. I'm like, well, I'm not going to pick a ball and golf all day, so give me something else to do. That's what I've been doing. What leadership qualities do you think are most important when you're managing both your property management team and your homeowner relations, your guest relations, what leadership qualities do you think are the most important? I think I had to be very honest with myself and make a list of what am I good at, what do I love doing, what do I not want to do, and what am I not good at? And you put them into those four buckets because when you're starting out, you own this. It's your money. Every nickel counts, every move you make makes impact. And so figuring out what can you delegate and what can you delegate with trusting somebody? How do you hire people that you can trust that have your same work ethic? And then you have to ask yourself, if I find the right person, but maybe they need to be maneuvered a little bit into how you really need unmolded. How do you do that? How do you keep them? How do you compensate them? It's a lot. Are you using any of those corporate tools to choose your team members? Yes, I have. I've used a couple that I did this one assessment. I forget the name of the tool, but it showed me and it told me who I would work best with. And didn't I hire someone originally? That person was great, but it wasn't really the right fit for me at that moment. In the time of the building of the business, I wasn't ready to have an employee is basically what I was saying. I thought I was, but I wasn't. That first part of team building is always the hardest. It really is. Looking ahead, what trends do you think are going to shape property management most? That's a big question. So I see that some of the OTAs, meaning the VRBOs, the Airbnbs, everybody, everybody wants to own the guest, everybody wants to own the experiences, everybody wants to own the pricing, the merchandising, marketing to get there. And the hardest piece for me is the property manager. That's visions and who I use to market through still needs to remain what I control because I'm the one with the contract with the owner. So I'm trying to figure out how do you navigate that you need all these different OTAs but still remain in control of the trust with your owner, the trust with the guest and make money because it seems like everybody's just piling on with taking the money down to the bottom of the barrel and that's not sustainable for the industry. Yeah. And the reasons, I mean we all know why the OTAs want to own the guest. The thing that I find so, so egregious in many ways is the fact that you have to own the guest. Because in property management, the pieces that we need to be very profitable, they are dependent upon owning the guest. For instance, any type of upsell, any type of thing that you want to do for them, like you're talking experiences as well. When you do something from your office, you get 100% of that profit. You're not having to split that with an owner. So any type of add ons and that type of thing that you can do that give you 100% of the profit, those are really where a lot of your ancillary income can come from. And that's really a part, I think of balancing your revenue and your portfolio as a property manager. So I agree with you. I think the future lies in trying to take back as much as we can of our own guest data, even though we're using third parties. And I mean everybody's talking about that today. Yeah. I will say this as an example, when the people we're marketing through control the guests information or the ability for us to talk to them during the reservation process, the negotiating process many times, and this is a trend is it's moving from short term rentals to 30 night minimums and that's driven by the HOA or the Golf community development. And so there's a lot of paperwork that needs to transpire between the guest and something I don't control, which is the hoa, they rule. So if I can't communicate effectively, share all those data points, give them the application links because I'm being restricted. It's not good for the guest. So I've been fighting back on that. Not a lot I can do to control it, but I find whatever way I can to get to the guests, say, listen, I'm just trying to be transparent. There's a couple hundred bucks extra. You got to pay an application fee, you got to get this evaluation filled out. But it's hard. I got to just tell you, as a leader and with your experience, you sound like you would be very good in joining some of the advocacy efforts that the vacation rental space has open right now, especially since you understand so much the fiduciary duty that you have to your guests. That's what I hear you talking about. So I would encourage you to become involved and I would encourage everyone to become involved with advocacy that's local to your area, because you're the one on the ground fighting for this and you're the one who is responsible to your guest. Ultimately, what has been the most rewarding part of your journey from enterprise technology into property management? I am proud that I'm doing this. And I always knew in my career that I always see things a year ahead. It happened to me, every piece of my career, every step, every company I was at, but I can never get people to listen to me or believe that I should be leading this stuff. And now I'm like, this is my baby. I do what I want to do. I can choose to go to sleep at 6pm or stay awake till 2, working on things. And I know there's a direct correlation to success and the fact that I just ran a business valuation for where I was at the moment about a week ago, and I'm pretty darn proud of the success we've had. And it just makes me feel good, like I can do this. I love that. I love that you're an encouragement to other people that are wanting to come into the industry or have thought about coming into the industry simply because they had a property rental themselves and they were like, hey, this will be something I might want to do and I might, as a leader, be able to do that. So if there are other people who are considering getting into property management or other people that are considering franchises, would you be willing to talk to them and give them advice from the trenches you've been in? Absolutely. I actually do it for new Sky Run franchise potentials. I love talking to them because I'm. It's just like this. It's real. Here's the things you gotta have your eyes wide open about and here's the easy stuff. But yeah, happy to. I would encourage you guys, if you're interested in anything that Kimberly has talked about, that you would get in touch with her. How would they reach you? North Napleskyrun.com and are you on LinkedIn? I am. All right. So you can always find her. It's Kimberly Layton. L A Y T O N guys, if you want to get in touch with her. So, Kimberly, outside of work, what keeps you recharged and stay inspired as a leader of your organization? I love that fun. I'm a huge pickleball advocate. I'm trying to work myself to be in the United States Pickleball Championships on an amateur basis next year. And then I love to golf. My husband's a scratch golfer. And we get out there and we just go and have a lot of fun. And then being with my family, just my family's. It's my world, so. And that should have been the first thing I said. Well, the fact that you're able to make your family your work is incredibly important. And that's the reason that so many other property managers have a job doing what they do, owning a company so they can do that. You create your own lifestyle, you truly do, based on what you love. So congratulations on being able to do that and being so successful. And thank you so much for being willing to share and being willing to share your knowledge to people if they reach out to you. You're very welcome. Thank you for having me. I enjoyed it very much. I really did. Thank you again. This episode of the Vacation Rental show was brought to you by itrip Vacations. To find out more more about how itrip vacations can help to grow your vacation rental business, visit itripfranchise.com make sure to search for the vacation rental show in Apple podcasts, Spotify and YouTube or anywhere else podcasts are found and hit subscribe so you never miss an episode. On behalf of the team here at Inhabit, thanks for listening.