Director of Recreation and Resident Life

Director of Resident Life

The Greens at Cannondale | Wilton, Connecticut

Help residents thrive through connection, purpose, and belonging.

The Greens at Cannondale is an award-winning, privately owned assisted living and memory care community in Wilton, Connecticut. We are seeking an experienced, compassionate leader to serve as our Director of Resident Life, overseeing programs and services that support residents’ mind, body, and spirit.

This leadership position encompasses resident activities, entertainment, enrichment, exercise, religious services, transportation, and concierge services. The Director manages a 10-person team delivering services seven days a week and helps new residents feel welcomed and connected to community life.

Our Evergreen Memory Care community includes 51 apartments, making expertise in Alzheimer’s disease and other dementias essential to this role.

Responsibilities

• Lead, coach, schedule, and support a 10-person team, ensuring consistent service and programming throughout the week.
• Develop a varied, meaningful resident life program for assisted living and memory care, reflecting residents’ interests, histories, preferences, and abilities.
• Oversee activities, entertainment, educational and cultural enrichment, exercise, spiritual programming, and religious services.
• Create individualized and group engagement opportunities for residents with Alzheimer’s disease and other dementias, adapting approaches as needs change.
• Train and guide staff in dementia communication, meaningful engagement, and approaches that support dignity, comfort, and choice.
• Oversee transportation scheduling and coordination for appointments, outings, and community programs.
• Supervise concierge services to ensure a welcoming, responsive experience for residents, families, and visitors.
• Welcome new residents, learn their interests and preferences, and help them develop relationships and a sense of belonging.
• Collaborate with nursing, dining, sales, and other departments to coordinate resident services, events, and transitions.
• Maintain strong relationships with families, entertainers, instructors, clergy, volunteers, and community partners.
• Manage departmental resources, purchasing, and expenses responsibly.
• Evaluate resident participation and feedback to continually improve programs and services.
• Communicate proactively with the Executive Director and follow through on departmental priorities.

Qualifications

• Demonstrated leadership experience in senior living, recreation, life enrichment, resident services, or a related field.
• Strong knowledge of Alzheimer’s disease and other dementias, with practical experience developing and adapting memory care programming.
• Proven ability to supervise staff, manage schedules, set expectations, and build an accountable, supportive team.
• Excellent organizational, communication, and problem-solving skills.
• Ability to balance creative programming with the operational demands of transportation, concierge services, and departmental management.
• A warm, professional manner and a commitment to residents’ dignity, independence, and quality of life.
• Relevant education in therapeutic recreation, gerontology, human services, or a related field preferred.
• Therapeutic Recreation Director, Certified Dementia Practitioner designation, or related credentials preferred.
• Availability to support a department operating seven days a week, including occasional evening, weekend, and holiday events.

Why The Greens?

At The Greens at Cannondale, resident life is central to our community. This is an opportunity to lead an established team, work closely with community leadership, and shape experiences that help residents feel known, valued, and engaged.

At The Greens at Cannondale, you'll find more than a job—you'll find a team that truly cares. Our mission is to create a warm, engaging community where residents thrive, and that starts with supporting the people who care for them every day.

As a member of our team, you'll enjoy:

A welcoming, respectful workplace where your contributions are valued.
Meaningful relationships with residents, families, and coworkers.
Opportunities for professional growth, training, and career advancement.
Leadership that listens, supports, and recognizes great work.
Competitive pay and comprehensive benefits for eligible employees.
A commitment to teamwork, innovation, and creating an exceptional resident experience.
We're proud to be a Great Place To Work® CertifiedTM community, based on feedback from our own employees. That recognition reflects the culture we've built together—one where people feel respected, supported, and empowered to make a difference.

Whether you're just beginning your career or bringing years of experience, if you're passionate about serving older adults and want to be part of a team that values compassion, excellence, and connection, we'd love to meet you.

Come grow your career where your work truly matters. Join The Greens at Cannondale.