Lifestyle Director

Trailwinds Retirement Community is opening in the Wildwood, Florida area this Summer- 2026!

We are beginning interviews now; training for this role will begin towards the beginning of July.

 

We're building something special and we're looking for passionate individuals to be part of it from the start. 

 

Not seeing the right fit just yet? Stay tuned, additional opportunities will be posted soon! 

About the Role 

As our Lifestyle Director, you’ll play a key role in shaping a vibrant, positive community culture and enhancing residents’ quality of life. You’ll deliver a resort-style lifestyle through thoughtfully planned social, educational, and wellness programs that support residents’ mind, body, and spirit while fostering strong relationships and a sense of community. This role is a member of the community Focus Team and reports directly to the Community Managers. 

What We’re Looking For 

• Must be at least 21 years old (25+ preferred for shuttle driving) with a valid driver’s license and clean driving record. 
• Flexibility:  Your primary schedule is a Monday-Friday hourly schedule, plus the ability to flex hours to cover evenings, weekends, and holidays as needed for events. 
• Minimum of 2 years of customer service experience and demonstrated leadership or community management skills. 
• Strong knowledge of the local community and a genuine passion for serving seniors. 
• Experience coordinating or leading events, social/recreational activities, wellness programs, or fitness classes; regular participation with ability to learn is acceptable. 
• Ability to work independently and collaboratively, with strong organizational, time management, and communication skills. 
• Experience with budget management and proficiency using technology for community content, including Microsoft Office programs and email. 
• No specific education or certifications required; fitness certification or coursework in business, gerontology, wellness, hospitality, marketing, or psychology is a plus. 

In this role, you’ll need to be comfortable with the functional aspects of the job, including:   

• Serving alcohol (must be 21+ and meet all local requirements). 
• When at least 25 years of age, you will be expected to  drive the community’s shuttle bus  for resident outings, and you must hold a valid driver’s license with a clean driving record.
• Securing appropriate  food handler permit as required by local ordinances within two (2) weeks of the first day of employment.

Key Responsibilities 

• Plan, implement, and continuously refine inclusive community events and activities aligned with resident interests and demographics by building strong relationships, gathering feedback, and evaluating success through surveys and attendance data. 
• Design and deliver  comprehensive lifestyle, wellness, and fitness programming that supports mind, body, and spirit, including leading a diverse fitness schedule and coordinating complimentary classes with partner organizations and certified residents. 
• Develop and manage the annual budget for lifestyle programming, including negotiating with vendors and securing sponsorships to enhance event offerings without exceeding budget.   
• Use online tools to create and distribute monthly event calendars, newsletters, and internal marketing materials, collaborating with the Focus Team to promote programs through social media and other communication channels to maximize participation. 
• Oversee the scheduling of community facilities used for events and activities, ensuring spaces are prepared, safe, clean, and available to meet programming needs.   

Benefits for Full-Time Employees 

• Competitive compensation and benefits 
• Access your pay anytime 
• $341 benefit stipend per pay period to apply toward: 
  • Health, Dental, Vision 
  • Life Insurance 
  • Short- & Long-Term Disability 
  • HSA, FSA, LSA 
  • Accident & Hospital Indemnity 
  • Legal & Identity Theft Protection 
• Paid Time Off 
• 401(k) with employer match 

Why RLC? 

• Fast-growing, family-owned company with 60+ communities nationwide 
• Supportive leadership in a beautiful, resort-style environment 
• A purpose-driven role where you make a difference every day 

Join Our Mission 

At Resort Lifestyle Communities (RLC), serving seniors isn’t just a job, it’s a calling. When you join our team, you become part of a close-knit, servant-hearted community guided by our Core Values: Respect, Honesty, Kindness & Compassion, and Service Excellence. 

Together, we work toward four essential goals that guide our success:

• Happy Employees 
• Happy Residents 
• Full Occupancy 
• On-Budget Operations

Ready to Engage with Heart? 

Bring your servant heart to a place that feels like family.  Apply today, and our Team will follow up soon! 

EOE/ADA

#urgent