Tropical Escape Vacation Homes Supercharges Growth & Guest Services With Extenteam

Founded in 2006, Orlando-based Tropical Escape Vacation Homes operates in an area that was hit particularly hard by COVID travel restrictions. But when those restrictions started to lift, the company found itself facing a totally different challenge: filling staffing gaps in the wake of the pandemic, as the vacation-rental market roared back to life. Then, company founder Matthew Daniel discovered Exenteam’s remote staffing solutions through an industry masterclass. And everything changed.

As Orlando-area destinations Walt Disney World and Universal Studios started to welcome visitors again, Tropical Escape was poised for its own resurgence. So much so, that after nearly 20 years in business, the company opened up two additional locations, bringing their portfolio to 215 properties. There was just one problem: “Price changes, inflation, labor shortages–all of these things that we didn’t have pre-COVID really changed the look and feel of the workforce here,” notes general manager KellyAnn Beach. 


And while Tropical Escape attempted to bring back staff they had furloughed during the pandemic, “We realized pretty quickly there was a lot of work, and not enough of… us,” Beach says.

florida vacation rental resort guest services Extenteam

Reservations weren’t able to be optimized. Guest experience and reviews were at potential risk. Staff was overworked and overwhelmed. Out of desperation, Tropical Escape tried out a call center, “but it wasn’t what we were hoping it was going to be,” Beach says.

Then one day, “Matthew came to me and said, ‘We heard about this company called Extenteam, we want to see what you think.’ I was like, ‘Yeah, let’s go!

Tropical Escape onboarded its first Extenteam team member, in a guest services role, in 2021. Two additional Extenteam team members quickly joined the company’s expanding remote team, which now totals four dedicated team members, serving in guest services and accounting positions.

Beach is quick to point out that getting the best out of her Extenteam pros requires a team effort. That means equipping her team members not just with comprehensive information on Tropical Escape’s properties, and the same SOPs utilized by her internal staff members, but with a communication infrastructure that encourages inclusion, and the freedom to interact as both integral workforce members and human beings.

“We work in Microsoft Teams, so our Extenteam members are in our daily chat with us. We try to learn more about them as people, not just staff. They are not just remote assistants answering our phones and helping our guests. Each one is a Tropical Escape team member. We’ll talk to them all day long. We’ll crack jokes. We’ll send GIFs. We’ll ask about their families, what they’re doing for vacation. If they’re not feeling well, we want to know, and we want them to know we’re here to help.”

In addition to full-time team members, Tropical Escape has recently added another layer of Extenteam coverage to her guest-services operation: Extenteam’s Tailwind 24/7 guest communications service.

Realizing that her rapidly growing property management operation needed extra help on nights and weekends, when full-time staff was off the clock, Beach turned to Extenteam’s Partner Success managers for an answer. “They mentioned a beta test they were doing with a new shared guest communications service, and I thought, THIS sounds delightful!”

That beta program, Tailwind, is now one of Extenteam’s most popular solutions for growing property-management companies seeking a scalable professional guest-services solution that doesn’t just pass along questions and problems, but solves them.

“Since we already had dedicated Extenteam team members, we knew the caliber of individuals the company was able to bring in. We thought, ‘They’ve given us great dedicated team members in the past. If Tailwind is pulling from the same pool, there’s no reason it wouldn’t be the same type of service.’”

And sure enough, Beach says, it was.

“Our Tailwind guest services staff are great. They really give guests that empathy piece. They go out of their way to assist guests,” Beach notes, explaining that Tropical Escape now uses Tailwind shared-service coverage for after-hours support across multiple properties in multiple locations.”
- KellyAnn Beach
Tropical Escape Vacation Homes

Beach says Extenteam has helped Tropical Escape scale without growing pains, while keeping guests happy, and return business robust. 

And she wants vacation-rental property managers in other parts of the country to know there’s a solution for their staffing challenges, too.

“It’s really important, whether you’re looking for a remote staffing company or you just know you have a problem that needs to be solved, that you find a company that puts effort and dedication into the team members they’re recommending to you,” Beach advises. “Extenteam doesn’t just say, ‘Here’s someone for your account, good luck.’ It truly is a partnership,” she says. “They’re going to find good talent, talent that can provide what you need. And if it’s ever not a good fit, they’ll continue to search until they find the best fit for your account.”

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