Dining Room Supervisor

Trailwinds Retirement Community is a new, upscale senior living community opening in Wildwood, Florida, in the summer of 2026. As part of Resort Lifestyle Communities (RLC), a fast-growing, family-owned company with over 60 communities nationwide, Trailwinds represents the next chapter in our mission to serve seniors in a beautiful, resort-style environment. At RLC, we emphasize a purpose-driven role where every team member makes a difference daily, fostering a culture centered on respect, honesty, kindness, compassion, and service excellence. Our company prioritizes happy employees, happy residents, full occupancy, and on-budget operations as the pillars of our success. Joining Trailwinds means becoming part of a close-knit, servant-hearted community focused on providing an exceptional lifestyle experience for our residents.

The Dining Room Supervisor role at Trailwinds Retirement Community is a critical leadership position within the community's dining services. This full-time role offers a competitive compensation package and an enriching opportunity to be part of a dynamic leadership team shaping the dining experience for residents and guests alike. The position involves acting not only as a lead server during meal periods but also as a proactive supervisor committed to maintaining high standards of service, cleanliness, and operational efficiency.

The Dining Room Supervisor will oversee the dining service quality, ensuring that every meal is more than just food on a plate – it’s a moment of meaningful connection for the residents. You will have a hands-on role that includes hiring and onboarding servers, providing essential training, coaching, and development support, as well as aligning team schedules with the RLC labor model. In addition, maintaining the dining room’s cleanliness, organization, and system adherence per RLC’s Operations Guide is essential, including overseeing the Chef's Pantry and Bistro areas to uphold excellent presentation and sanitation standards.

As a community leadership team member, you will participate in leadership meetings, collaborate in planning events, and contribute to overall business objectives to enhance the resident experience continuously. The primary schedule is Monday through Friday from 11:00 am to 7:30 pm, with occasional additional hours required for special events and holidays. Successful candidates must be at least 21 years old, possess basic Microsoft Office skills, have previous service leadership experience, and meet food safety requirements including ServSafe Manager certification and a Food Handlers permit. This is an exciting opportunity for passionate individuals eager to build something special from the ground up and lead with heart in a welcoming, supportive environment.