Lisa Lilly of SkyRun Vacation Rentals - Aspen Real Life


Lisa Lilly of SkyRun Vacation Rentals

SkyRun Vacation Rentals is a rapidly growing multi-location organization with over seven hundred properties in twenty-five locations. We have created the sweet spot in vacation rental management by combining the advantages of local ownership and management with the efficiencies, power, and support of a national brand. We also never forget that guests don’t just want to stay like a local, they want to play like a local and SkyRun ensures that happens. The owners use the properties regularly for themselves and friends and family, and have chosen to share their home with travelers like you!


Hi everyone, it’s Jillian Livingston, and I’m here with my Real Profiles Interview. Today I’m introducing you to Aspen Business Connect member, Lisa Lily. She is the Director of Client Growth and Happiness for SkyRun Rentals in the Aspen Snowmass territory.


SkyRun Vacation Rentals is a full-service Property Management Company. We kind of have found a sweet spot in that we are locally owned but we have the national brand backing, which can be very powerful so that we can do the marketing of your property. We have a whole Marketing team in corporate that can market your property for you and back our local team up. The differentiator with the local touch is that you have my cell phone number. Skippy Mesirow is our General Manager, whom almost everybody knows. He’s a force to be reckoned with, and it’s just great to work with him. The previous said, provides a lot of value to SkyRun, to have local people that can be there in 20 minutes, should something go wrong. Just being able to have those one-on-one connections, where today we can all get so disconnected, is really powerful. As well as the rental projection, we can save realtors a lot of time and be a present for them. None of us on the team are licensed agents, we have no desire to take away their clients. Their clients will always be their clients, so let us help you look a little better or save you time, which we could all use.  


We push out to about 65 different channels. We are one of the first proprietary software to have connected with VRBO and AirBnb way back in the day. We have 36 locations across the country, many of which are mountain-based. Now we have all sorts of properties, from condos to very nice luxury homes in Aspen and Snowmass. We do a lot with the real estate Community in the area. Because we can be a trusted advisor to them by creating rental projections, I can bring those projections to an open house and show up with them, and just have them in there. It looks really nice, and it’s a big time saver for realtors to lean on me to do that, and I can send it via PDF drop by your office. That’s part of my job, and I’m happy to do it. If you have a property that needs a rental projection and you need it quickly or if you think it would be beneficial for somebody from a vacation rental company to show up to an Open House, that’s what I’m here for. The other thing I want to mention, Jillian, is if maybe you have somebody that you know who wants to put their property on the vacation rental market, to make some extra money. You know, we pay very generous referrals to anyone in the community that wants to spread the SkyRun love.

DIRECTOR OF CLIENT GROWTH & HAPPINESS, yeah I was an Agent with them for about 15 years. The ski industry is in my blood, I’m the fourth generation in the valley. My grandfather ran the Breckenridge Ski area for a long time. It’s something that I love, the fact that I got to raise my children here, my twin girls, you know, it’s such a gift. It’s true when they say there’s no place on Earth like Aspen. For me to really have a good understanding of what that means and be able to help people kind of maneuver, that is where I can really come in and be effective. 

I started at and I stayed in the Vacation Rental Industry. I have very different capacities, I’m selling a lot of digital marketing. I went more to the tech side but always doing some sort of sales and being out with people. It’s been a long, longer than I’d like to admit really, fun career in this industry. I feel like this position really brings it full circle for me. I know the area and the ins and outs of the industry. So let me be a resource because people don’t know what they don’t know, so let me help.

What does my title mean? Well, you have to make it fun and personable. I think that right now, in general, that’s what’s lacking in life, those true connections. My goal is to make them more money, to know that SkyRun will take care of their property and that we will communicate to you; what is going on in the home. We have a Dashboard, so they have access to see what reservations are in. They know exactly how much money they’re making at any given time. So for me being the Director of Client Growth and Happiness, what can I do to make this easier for you? When people think of investing or putting their large investment in a property management pool, that can be really scary. If they can’t trust what I bring to the table and what SkyRun brings to the table, it’s not going to be a fit. By design, we don’t have a one to five-year agreement. Because if it’s not working for you, it’s not working for us. SkyRun is very much about building a true partnership, as opposed to just working for you. 

Communication: we will do the emails, we will do the text, and a lot of the communication before the arrival so that there are no surprises when somebody checks in. They have it all digital; they don’t have to call anybody if they don’t want to. We all know that most people don’t really like picking up the phone anymore. 


We do realistic rental projections that will tell you exactly within a range of five to ten thousand dollars what we think your property is going to earn that year. You know there are a lot of things that go into that but making our customers more cash is obviously top of mind. Then there’s the care for their property, making sure that they trust that it is being inspected, it is being cleaned. That if something breaks we are there to go fix it. Let me also be a trusted advisor for all these crazy new regulations that are going on everywhere. They’re crazy, they’re changing all of the time. I’ve put together some really informative one-sheets that I’m happy to send out for you to send to your clients if they can’t understand it. You know it’s hard for all of us to understand because it’s ever-changing. That’s one of my biggest jobs, to keep up with those changes so if there’s ever any question, I’m happy to answer questions around the regulations that are quickly happening in the Aspen Snowmass area along with all of the other mountain and Resort towns. We all know it’s very expensive to come to the Aspen Snowmass area therefore we have properties that range from the off-season at six or seven hundred dollars a night to the High season at ten thousand dollars a night. We are able to work with our owners to kind of let them guide that as well, we do a lot of dynamic pricing. We also have a lot of software around it, however, if somebody feels like, e.g. “ I never want my condo to rent for less than 500 a night,” that’s great we can set those parameters. We do cater to maybe a couple that’s coming in or a couple with two small children that have been saving for two years to bring them to Aspen Snowmass and also to those high-end clients that just want to come to have the luxury experience that Aspen provides.


How does it compare to getting a hotel room? I mean it seems like, if you have a whole family of five it’s going to be less expensive to rent.


You’re absolutely correct. If you have a couple of families, instead of getting two connecting hotel rooms at 500 a night each. Let’s look into a four bedroom, where we can share common space and food and cook and maybe not have to go out every night unless we want to, especially when traveling with families that can make life a lot easier, rather than having to order room service every time a child wants a pancake. 


Lisa thank you so much for sharing what you do, this gives us such a better idea of what Skyrun Vacation Rentals is all about. What is the best way that people can find you and find rentals?


Our website. Email: [email protected], it doesn’t get much easier than that. I would love for you to meet up for coffee, if you have any further questions regarding what SkyRun does or how maybe I can help you in any way, I’m always happy to be available for those conversations.


Well, thank you, Lisa. I’m so proud to have you as an Aspen Business Connect Member. I think it really shows the quality of the people we’re bringing in and you’ve been so helpful and involved with other people within the network. You just always come in with this smile and I’m really glad to have you on board thank you for this time. 


Thanks, Jillian, I appreciate you.

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