Four seasoned VR pros share how they have survived and thrived in the industry. 

In this series of VRM Careerists, VRM Intel is diving into the lives of the careerists among us, those managers who have made it over the river and through the woods of vacation rental life, and yet have still chosen to persevere in a business that is as rigorous as it is unglamorous, as challenging as it is heartwarming. 

The last story we have to share with you in this series of VRM Careerists is that of Cort Roussel.

Stepping Away with Full-Cort Advantage 

Perhaps the most relatable part of Cort Roussel’s story is how he stepped back from the vacation rental industry, as opposed to how he stepped into it. 

“The quality of life was gone,” he said quietly, as he reflected. “The dream was gone. At the end of the winter, my guests were skiing more than I was.” 

Overwhelm in the vacation rental management world is a common condition. But these days, Roussel, who is still owner of Franconia Notch Vacations (he sold his interest in the short-term rental part of his business to Vacasa), has dialed back his workload to include only long-term rentals of 90 nights or more. 

“It’s still an ongoing business cycle, but less stressed,” he said. “When things go wrong, you have more time to get it right. And I’m not having to manage both short-term and long-term rentals at the same time.” 

Roussel had always planned a life in hospitality. A self-described “well-educated resort rat,” he earned a bachelor’s degree in business, focusing on hotel and restaurant management. But his first position working in the timeshare arena left him frustrated. He was not always able to please his customers, whether they were owners or guests, because they didn’t always understand what they had purchased. 

“Most folks don’t get a lot of vacation time; maybe they go away four times per year,” he noted. “They dedicate a lot of time figuring out how they want to spend that time. The time someone gives you for vacation is inordinately valuable.” 

Roussel had been moonlighting for Loon Reservation Service, where he met then-company owners Jim and Barbara Collier, whom he credits as his greatest mentors in the industry. 

Within a year after being hired in 2000, he obtained his real estate license in New Hampshire and attended his first VRMA (Vacation Rental Management Association) conference as a result of their support. Roussell would later serve as a member of the board of directors at both VRMA and the Franconia Notch Chamber of Commerce. 

“I never had an employer invest that much,” he said. “And I had health care! They took care of their staff and treated us like family.” 

Roussel marvels at how the Colliers, then in their late 60s, were early adopters of everything the internet had to offer. He said they were already accepting reservations online in 2000 and had a T1 data line running through their office. 

“They snatched up all the dot-coms in the surrounding areas,” he said of the Colliers’ foresight in purchasing domain names. “No one even knew what a dot-com was.” 

By 2002, the Colliers had moved him into the management of Franconia Notch Vacations, and by 2005, they offered to sell that business to him, and he accepted. But the building itself was leased, not owned. Although the option to buy it was on the table from the landlord, Roussel could not afford to buy both the business and the building. 

“But are you interested?” Collier asked Roussel at the time. 

“He bought the building,” Roussel recalled, emotion rising in his voice. “I now own the building. They’re like parents.” 

He purchased the building from the Colliers over time and developed the business into a success that drew the interest of Vacasa. Along the way, he realized he was overworked by doing everything himself, and it was time to make a shift. 

He is happy to have more time on the slopes these days. 

“I’m semi-retired now,” he said. 

After more than 25 years dedicated to others, this careerist finally made time for his own vacations. 

Read More about Other VRM Careerists Below

Four seasoned VR pros share how they have survived and thrived in the industry. 

In this series of VRM Careerists, VRM Intel is diving into the lives of the careerists among us, those managers who have made it over the river and through the woods of vacation rental life, and yet have still chosen to persevere in a business that is as rigorous as it is unglamorous, as challenging as it is heartwarming. 

The next story we have to share with you is that of Kelly Keys Wilson.

Friendship Inspires Kelly Keys Wilson 

Kelly Keys Wilson started her career in vacation rentals in 1992 with Outer Beaches Realty in North Carolina right out of college as a bookkeeper. With a degree in finance, she was a good fit for what was then a small brokerage on Hatteras Island. 

“It was pretty neat because back then we were using computers, but we were still taking reservations on cards,” she said. “We posted payments in the computer, but we hand-wrote them on little ledger cards. It was so old school. We would use a highlighter and mark things off in a book. It was just the start of things becoming computerized.” 

Now president of the company, Wilson never left family-owned Outer Beaches Realty, which now manages approximately 400 properties. Over the past 29 years, she had the rare opportunity to “grow up” within the company and witnessed firsthand the evolution of the vacation rental industry. 

“I take pride in the hard work that has gotten me here,” she said. “I started in the proverbial mailroom and worked my way up to the position I have now.” 

Wilson has worked all sides of the vacation rental business but has stayed substantially focused on the financial side with special attention to property owners. She has to get her hands dirty, too, but does so most often in issues of real estate commission compliance, trust accounting, and, of course, expenses. 

“There are definitely two sides to it,” Wilson said of the vacation rental business. “Guests are important, but we work for the homeowner, too. They need to understand their statements. The financial side, the numbers side, is extremely valuable and important in evaluating your marketing and performance.” 

She notes that the Outer Banks area is highly competitive, and there is little room for error as managers are all trying to secure the best properties—and the best guests. But there was a break in that mentality when her company suffered a devastating fire in November 2014 at their main location, where their computer servers and phone systems were based. 

“The fire occurred in the wee hours of the night, but by the morning, we had (our competitors) offering us computers, asking ‘How can we help you?’ and ‘Can we bring you lunch?’” Wilson said. “A lot of places out there are so cutthroat. You would hate to think they would delight in your misfortune.” 

Wilson said her office was lucky in that they had a disaster recovery plan and, in the end, lost very little information. They were very fortunate, but what stays with her is the response from industry colleagues. 

“On a normal day, we want the most reservations and the nicest properties, but on a day like that, you put that aside and do what’s right,” she continued. “It’s very nice to know you have friends at these other companies.” 

Read More about Other VRM Careerists Below

Four seasoned VR pros share how they have survived and thrived in the industry. 

In this series of VRM Careerists, VRM Intel is continuing to dive into the lives of the careerists among us, those managers who have made it over the river and through the woods of vacation rental life, and yet have still chosen to persevere in a business that is as rigorous as it is unglamorous, as challenging as it is heartwarming. 

Next on our list is the story of Ryan Christopher.

Ryan Christopher Is Happy to Be Lazy, Finally 

Ryan Christopher was in college in 1995 doing a summer internship as a manager-in-training with Abbott Resorts in Florida when he learned firsthand that working in hospitality was not for everyone. 

“Eighty percent of the interns decided they didn’t want to do it and changed their degree by the end of the summer,” he said. “They never had worked, never had practical experience. You know, cleaning toilets, throw-up, all that stuff that happens. But you have to do it hands-on to be successful.” 

By the time he was 25, he was a general manager in the Fort Walton Beach area with the same resort company he interned for, hired right out of college by one of his mentors, Joann Saucier. He credits Saucier with demonstrating to him how to treat and appreciate employees, particularly the ones servicing the homes. 

“She was good about helping me understand what the real business was,” Christopher said. “It’s hard to get people to want to do some of that stuff. But she had empathy for employees. I learned how to manage people by watching her. I imitated what I saw her doing.” 

Even while managing hundreds of properties, in the early years Christopher stayed close to the guest experience. One guest called after checking in, saying there had been a homicide in his unit. But after further inspection—and a period of panic—it turned out the “blood” was only tomato sauce. 

“Another guest covered an entire unit with Saran Wrap,” he said. “It was just crazy. He was a germaphobe.” 

Christopher had the unique experience of working exclusively for large, publicly-traded vacation rental companies over the years, which offered advantages and disadvantages. While it was a luxury to have the funding to implement new technologies and have entire departments for marketing and human resources, there were restrictions and frustrations in effecting change. 

“The best analogy is you operate like an aircraft carrier when you try to change direction, rather than a speedboat,” he said. 

In 2020, he took his 22 years of vacation rental industry experience and pivoted to a new venture as the owner of Lazy Days Beach Services. Christopher is now a service provider for the vacation rental industry. He said that over his years of working in Florida, he saw a sizable gap in the vacation rental guest experience. 

“If we were able to do everything perfectly (at the vacation rental), but guests went to the beach and had a horrible experience, they felt like that was an extension of what we were,” he said. “I saw an opportunity to use what I learned in vacation rentals and leverage it.” 

Lazy Days Beach Services provides beach concierge services to large companies like Marriott and condo associations, but also to nearly 1,000 individual vacation rental homeowners who see the value in ensuring that their guests have the ultimate beach vacation experience from start to finish, so they’ll return year after year. 

And now, with Lazy Days, he also has time to serve as manager of his own three vacation rentals. He finally has the power to effect the change he wants, whenever he wants. 

“I can’t tell you how exciting it is to immediately affect that guest experience as an owner,” he said. “I love it.” 

Read More about Other VRM Careerists Below

Four seasoned VR pros share how they have survived and thrived in the industry. 

If there is one universal truth about vacation rental managers, it’s that they did not tell their parents they wanted to be one when they grew up. Unlike that of an astronaut or veterinarian, the road into the vacation rental industry is not paved or even clearly marked. 

Some might say it’s muddy, and you better be wearing boots. 

In this series of VRM Careerists, VRM Intel is diving into the lives of the careerists among us, those managers who have made it over the river and through the woods of vacation rental life, and yet have still chosen to persevere in a business that is as rigorous as it is unglamorous, as challenging as it is heartwarming. 

They remember when marketing meant mailing out print catalogs. They rattle off long lists of reservation software, tried and long abandoned. They have stories straight out of reality television. 

And they know way too much about toilet paper. 

These are their stories, just as personal as the vacation memories they create for guests. The first story we have for you is Kathleen Homes.

Kathleen Homes Gets Down and Dirty 

Kathleen Holmes was looking for health insurance when she stumbled upon a front desk position with Great Beach Vacations in Charleston, South Carolina, in the mid-1990s. With a master’s degree in urban anthropology, it might not have seemed like an obvious fit. 

“It was like answering phones at the DMV,” she remembers. “It was just insane with requests. ‘I just checked in and there’s no toilet paper!’ And you would have thought it was the end of the world. You’d have to talk guests off the ledge, use your active listening skills, and validate concerns.” 

Within six months of deftly juggling phone calls from guests, vendors, and homeowners, Holmes was promoted to a property manager position and was one of five owner relations managers handling more than 400 vacation rental properties between them. 

Now with 20 years of industry experience, and currently working as director of marketing and acquisitions for Seabrook Exclusives, Holmes knows she found her calling. She and her team pride themselves on staying focused on personal connections in this age of automated everything. 

“We really still want to get on the phone with people and stay in front of them throughout their journey,” Holmes said. “Our best attribute is our relationship with our guests.” 

The proof? Seabrook Exclusives has a 67 percent returning guest rate. 

“We sell service, experiences, and we help our guests craft memories,” she said. “The human factor is always going to be the most important thing we can offer.” 

Holmes enjoys getting her hands dirty in all aspects of the business and is known by her team to wield a pretty mean vacuum cleaner. By her admission, she’s also a little heavy handed with the Tilex spray. 

“You only become a good vacation rental manager by being in the trenches,” she said. “Taking reservations, cleaning, fixing things-being a MacGyver. 

“My husband is blown away. I’ve gone outside and fixed our A/C, looked at our water heater, and said, ‘Yeah, we’ve got an upper element out.’ And he’s like, ‘Whaaaat?’” 

Holmes has a special touch when it comes to air conditioning, demonstrated by one of her favorite stories. Guests at an oceanfront property called in one day saying the living room wasn’t cooling properly, and despite a technician telling Holmes the system was cooling within range, she remained skeptical. 

She decided to call two other contractors and bring them with her into the dark crawl space under the house to check the ductwork. As she guessed, the duct under the living area had a large hole in it, and cool air was pouring into the crawl space—likely the work of rodents. 

But then one of the technicians pointed his flashlight into the sand near their feet. Large paw prints. 

“Hmmm. Bobcat,” he whispered to Holmes. 

“We all lean down and start to see this outline of a mummified bobcat in the sand and the contractors are on either side of me,” Holmes recalled. “And I can’t scream because there are guests in the house right above me, so I dug my nails into them. They both started laughing. They thought it was cool!” 

Vacation rental management requires being ready for everything. 

“I will never say I’ve seen it all,” she said. “Because in this business, there’s always something new.” 

Read More about Other VRM Careerists Below