What are the responsibilities and job description for the Lifestyles Director position at The Mayflower at Winter Park?
Lifestyles Director
Reports to: Director of Marketing & Brand Engagement
Location: The Mayflower at Winter Park
Status: Full-Time | Exempt
Make Community Connections. Create Meaningful Experiences. Have Fun Doing It.
At The Mayflower, life doesn’t slow down—it evolves. Our residents are accomplished, curious, wellness-focused individuals who have led robust professional and personal lives. We’re looking for a dynamic, relationship-driven Lifestyles Director who is excited to curate experiences that continue to enrich, inspire, and connect them to the world around them.
This is not a “corporate” role. The Mayflower is a single-site, not-for-profit community, which means real-time decision making, and the opportunity to see your ideas come to life—quickly. If you love building partnerships, designing engaging programming, and creating joyful moments that truly matter, this role is for you.
As the Lifestyles Director, you’ll lead and oversee the Lifestyles Department, Concierge, and Transportation, ensuring a seamless, vibrant experience for our independent living residents.
You’ll be the connector—the person who brings the greater Winter Park and Orlando community into The Mayflower, creating programming that is:
- Stimulating
- Entertaining
- Educational
- Wellness-centered
From cultural outings and guest speakers to fitness, lifelong learning, and social experiences, you’ll design programming that reflects the intellect, curiosity, and sophistication of our residents.
Key Responsibilities Include:
- Building and nurturing meaningful relationships with local organizations, cultural institutions, universities, wellness professionals, and community partners
- Curating innovative, high-quality lifestyle programming that supports social, intellectual, physical, and emotional wellness
- Leading and mentoring a passionate team across lifestyles, concierge, and transportation
- Collaborating closely with Marketing & Brand Engagement to align programming with The Mayflower’s brand and community presence
- Ensuring exceptional customer service at every touchpoint—this role is highly resident-facing
- Managing vendors, entertainers, educators, and speakers with a focus on quality and creativity
- Making thoughtful, resident-centered decisions quickly and independently
Who You Are
- A people-person who thrives on connection, creativity, and collaboration
- Naturally customer service–driven with a warm, professional presence
- Equally comfortable planning big-picture strategy and executing day-to-day details
- Energized by working with intelligent, engaged seniors who value purpose and wellness
- Excited by autonomy and ownership.
Qualifications
- Minimum of 5 years of experience in lifestyles, hospitality, programming, community engagement, or a related field
- Proven experience leading teams and managing multiple departments or service areas
- Strong organizational, communication, and relationship-building skills
- Passion for wellness, lifelong learning, and community engagement
- Bachelor’s degree preferred
Why The Mayflower?
- Single-site, not-for-profit community—your ideas matter and move fast
- A culture of trust, collaboration, and creativity
- Residents who are intellectually curious, accomplished, and deeply engaged
- The opportunity to make a real impact on people’s daily lives
What Employee Benefits You'll Receive
Our Excellent Benefits Program includes:
- Medical Insurance Company Paid Plan available to cover premium for employee, spouse and dependent(s). Additional plans are available at a reduced premium.
- Dental and Vision Insurance Company Paid Plan to cover premium for employee, spouse and dependent(s).
- Company Paid Life and AD&D Insurance
- Company Paid Long Term Disability (LTD) Insurance
- Cell Phone Reimbursement
- Supplemental Voluntary Life Insurance for Employee, Spouse and Children; supplemental benefit options available at employee cost
- Paid Time Off and Paid Holidays
- 403(b) Retirement Plan with Company Match*
- Free Freshly Prepared Meals for You to Enjoy Daily
*See HR for details.
At The Mayflower, you’re not just planning activities—you’re shaping experiences, building community, and enhancing lives.
All job applicants are required to successfully complete an AHCA Level 2 Criminal Background Check. More information and education on this requirement may be located at https://info.flclearinghouse.com.
The Mayflower, an Equal Opportunity Employer, values the diversity of our team in delivering a world class resident experience.
Job description available upon request.
Apply today and bring your passion for life to The Mayflower!