How Bennett Built a Career From Disney Vacation Club Opening Team Member to Guest Experience Manager
What can a career in Disney resort operations look like over more than three decades? For cast member Bennett, it's included helping launch the first Disney Vacation Club Resort and the first ship in the Disney Cruise Line fleet. His career has also included opening resort hotels at Hong Kong Disneyland Resort, Shanghai Disneyland Resort and Walt Disney World Resort. Each experience has deepened Bennett's connection to Disney and appreciation for creating memorable guest experiences.
Today, he serves as a Guest Experience Manager at The Cabins at Disney’s Fort Wilderness Resort, where he draws on the leadership skills, operational experience and attention to detail he has developed throughout his Disney career.
As Disney Vacation Club celebrates its 35th anniversary, Bennett reflects on the experiences that shaped his career and the lessons candidates can take from his journey in resort operations and leadership.
Opening the First Disney Vacation Club Resort
Bennett’s DVC story began in 1991, when he helped open “Disney Vacation Club Resort,” the flagship resort known today as Disney’s Old Key West Resort. Thirty-five years ago, this Florida Keys-inspired destination was the first to invite guests to “own a piece of the magic.” Bennett, part of a proud group of opening-team cast members still making magic at The Walt Disney Company, now serves as Guest Experience Manager at The Cabins at Disney’s Fort Wilderness Resort, the 17th Disney Vacation Club Resort.
“If I could put my Disney career into a bottle, there isn’t a single thing I would change,” Bennett said, reflecting on a career still going strong after 36 years, fueled by the philosophy of our company’s founder. “Whatever you do, do it well,” Walt Disney once said. “Do it so well that when people see you do it they will want to come back and see you do it again and they will want to bring others and show them how well you do what you do.”
With Walt’s words guiding him to uphold what cast members know as “The Disney Difference,” Bennett approaches each day with an attention to detail and a relentless drive to turn “good” into “unforgettable.”
Creating memorable experiences for Disney guests
One of Bennett’s favorite magic-making moments, for example, came while arranging, for a young fan of Walt Disney Animation Studios’ The Little Mermaid, a surprise meet-and-greet with Disney Legend Jodi Benson, a Disney Vacation Club Member Cruise mainstay best known for her role as the voice of Ariel in the film. The moment materialized during the inaugural sailing of the Disney Wonder ship (another ship that Bennett helped launch), on which Benson appeared as a featured guest. More than a quick “hello,” the private meet-and-greet culminated with the Disney Legend serenading the young guest with the Ariel anthem “Part of Your World,” creating a core memory that the fan and her family would treasure for years to come.
“It was an incredible experience for the family, and Jodi was gracious enough to make it happen. I just love what I do and want to make sure each guest experience is as memorable as possible,” Bennett said, adding that moments like these are what make Disney, well, “Disney.”
That same sense of creating happiness is what drew Bennett to Disney Vacation Club 35 years ago. More than the opening of a new resort, the introduction of Disney Vacation Club marked the beginning of a new way for families to experience the magic, transforming Disney Resorts into places they could truly call “home.”
At the time, Bennett had been with The Walt Disney Company for only a year, working the front office at Disney’s Grand Floridian Resort & Spa (now “home” to Disney Vacation Club villas). Being approached by his leader with an opportunity to work overnight shifts as a leader at the new “Disney Vacation Club Resort” was, according to Bennett, “an offer I couldn’t refuse.”
Bennett's early years in Guest Services
This multifaceted role touched nearly every aspect of the Member and guest experience. Throughout the night, Bennett helped keep resort operations running smoothly, supporting everything from the front office to bell services to housekeeping. And he loved every minute.
Although working third shift meant missing the morning’s ribbon-cutting ceremony and the first chorus of “Welcome home, Members,” Bennett said the nighttime gig was equally rewarding because he was doing what he loved most – enhancing the guest experience while also developing leadership skills that would shape his career.
“It was interesting because all of us were learning as we were going,” Bennett recalled of those early days in the Disney Vacation Club neighborhood. “I remember our leaders telling us that this place was as much ours as it was our Members’ and to make it our own.”
Those words have stayed with Bennett ever since, reinforcing the role every cast member plays in creating that sense of belonging, something that has defined Disney Vacation Club since day one.
Bringing his Disney Vacation Club career full circle
While Bennett’s career has taken him around the world and to many areas of the company, Disney Vacation Club has always felt like “home.” Today, as a Guest Experience Manager at The Cabins at Disney’s Fort Wilderness Resort and as a Disney Vacation Club Member himself, his journey feels “full circle.”
“Disney's Old Key West Resort is still our favorite place to stay,” Bennett said. “It’s not a time capsule of 1991, of course. We’ve made enhancements and redesigns over the years, but the nostalgia is there. Every time we stay, it feels just as exciting as it did the first time. That’s what makes being a Member so special. It keeps growing and changing, but somehow still feels like coming home.”
