After more than two decades at Chevy Chase Club, Luke O’Boyle is settling into a new role at Windsor in Vero Beach, Fla. The move represents both a change in scenery and a shift in governance structure, but it is also the continuation of a career built on thoughtful leadership and mentorship.
“I wanted something totally different,” says O’Boyle. “I had the privilege of being at a large, full-service metropolitan area country club for over 20 years and enjoyed it immensely. But as we wrapped up $33 million in construction at Chevy Chase and my kids went off to college, I knew there was never going to be a better time to step away and leave the club in as good a place as I possibly could.”
Family ties to Florida helped guide the decision, but Windsor quickly became more than just an appealing option. “When I visited, I felt a sense of intent in everything that had been done here,” he says. “The architecture, the landscaping, the feel of the place; it was all very distinct. It did not feel like any other Florida community. That intentionality reminded me of what I had experienced at Chevy Chase and convinced me this could be the perfect transition.”
A Community by Design
Windsor is a 472-acre community with 350 homes and an equal number of memberships. Members and residents enjoy a beach club with oceanfront dining, a cabana bar and a pool, along with 18 holes of golf, eight tennis courts, an equestrian center, croquet, and fitness. Pickleball and padel are being added this season.
“It is considered a sporting club in a private residential community,” explains O’Boyle. “Most members are here November through May, but we do have year-round residents. We employ about 250 people in season and 145 in the summer months. With that many touchpoints for food and beverage, golf, racquets, and equestrian, it is a much bigger operation than the membership numbers might suggest.”
Windsor also features amenities rarely found in similar communities, such as a post office and a town hall that doubles as a chapel. “It was designed by a very well-known architect and is considered one of his signature buildings,” O’Boyle says. “It adds another layer of distinction to the community.”
Governance in Transition
Unlike his previous clubs, Windsor is still under private ownership. The community and club are owned by a Canadian family that intends to turn governance over to the membership within five years.
“For me, governance is a big piece of this role,” says O’Boyle. “At Chevy Chase, we had strong committees that functioned in a truly advisory capacity. They were a resource for the senior management team. Here, we are just beginning to establish committees. To be part of that from the outset and to help provide structure so that the experience is productive and collaborative is exciting.”
His experience with national associations also adds value. “Between my 20 years at Chevy Chase, my time on the NCA board, and my time on the CMAA board—both of which required bylaw revisions—I feel well prepared to help Windsor refine its documents and prepare for a smooth transition,” he says.
Setting the Pace
Starting fresh after two decades in one place is not without its challenges. O’Boyle is approaching the first year with deliberate patience.
“I want my actions to be intentional,” he says. “I do not want to come in with the mindset of, this is how I did it before so this is how it has to be done here. I have to learn the culture first. I have to understand the staff and listen to members. Then I can prioritize changes that are going to have the biggest impact.”
The foundation is strong. His predecessor, Bob Gallagher, served Windsor for 12 years. “[Gallagher] left a great culture,” says O’Boyle. “I need to build on that, especially as we prepare for turnover and the transition from private ownership to member ownership. That will require more financial responsibility and a different approach than having the benefit of a family who has invested in the community as a passion project.”
Mentorship as a Legacy
If there is a through line in O’Boyle’s career, it is mentorship. He left Chevy Chase with a scholarship established in his name for employees pursuing professional development. “That was always what I hoped my time there would be known for,” he says. “Helping people reach their potential, whether that meant advancement within the club or moving on to become a general manager elsewhere.”
At Windsor, he plans to continue creating those opportunities. “First, I want to make sure staff are connected to professional development,” he says. “Second, I want to spend time with people and help them see the bigger picture. I want the golf course superintendent to understand how his decisions impact food and beverage and how that impacts our ability to sell real estate. The more well-rounded the team becomes, the stronger the experience for members.”
That focus extends to the club’s newest expansion, the North Village. The development includes 34 home sites and six row homes, with more than half the acreage devoted to green space, parks, and lakes. “It was designed with a focus on sustainability and native plant material,” O’Boyle says. “It is intended to complement the wildlife refuge that borders the community. Even within Windsor, it will have its own distinct feel.”
Building Connections
Though new to the area, O’Boyle has already found a supportive network of peers. “The Vero Beach club managers have been very receptive,” he says. “They hosted a dinner with 10 or 11 of my peers, and when my spouse moves here in September, they are planning something with spouses as well. There is a lot of camaraderie in this community.”
For O’Boyle, Windsor is both a new chapter and a natural continuation of his leadership philosophy. “It feels intentional and thoughtful,” he says. “That is the kind of environment I wanted to be part of, and I see a lot of opportunity here.”
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