Engagement Specialist, Assisted Living

Why You’ll Love Working at Milestone

Milestone is one of the fastest-growing senior living operators, with 100+ years of combined industry and hospitality experience. We focus on teamwork, creativity, and making a real impact for our residents and staff.

Perks & Benefits

• Medical, Dental, Vision (full-time employees)


• 401(k) with employer match


• Generous PTO


• Pet insurance


• Perks at Work


• Employee Assistance Program


• Voluntary benefits options

About the Role
We’re seeking an Engagement Specialist – Independent & Assisted Living (AL/IL) to oversee resident engagement programs and implement Milestone’s 6 Principles of Well-Being. In this role, you’ll design and manage the monthly calendar, coordinate internal and external events, develop community partnerships, oversee volunteers, and ensure residents enjoy meaningful and enriching experiences.

What You’ll Do

• Interview all new residents within 7 days of move-in to assess interests using the Resident Interest Worksheet


• Provide new resident orientation to available programs and opportunities


• Continuously assess residents’ preferences and recommend programs to meet their needs


• Utilize “Get to Know Me,” Resident Interest Worksheets, and “25 Things” tools to guide engagement


• Develop a monthly calendar designed to stimulate residents intellectually, physically, socially, and spiritually


• Coordinate and manage daily activities while staying within budget


• Secure and coordinate internal and external entertainment aligned with resident interests


• Collaborate with leadership in interdisciplinary meetings


• Plan and execute quarterly marketing events with Sales & Marketing and Culinary leadership, including planning, set-up, clean-up, and promotion


• Coordinate transportation for off-site activities, including sightseeing, medical visits, and destination outings


• Ensure safe work practices and compliance with Safety Committee standards


• Support the Executive Director with investigation and follow-up of workplace injuries as needed


• Foster teamwork, take initiative, and support coworkers, residents, and visitors


• Perform other duties as assigned

What We’re Looking For

• High School Diploma or equivalent required; Associate or Bachelor’s degree strongly preferred in Social Service, Business, Recreation, or a related field


• Minimum three years of experience in assisted living preferred


• Proven ability to lead and manage staff


• Strong written and verbal communication skills


• Excellent interpersonal, relationship-building, and mediation abilities


• Strong organizational skills with the ability to prioritize, plan, and follow through


• Ability to work independently, make decisions, and remain calm under pressure


• Proficiency with Microsoft Word and Excel preferred


• Pleasant, professional, and personable demeanor


• CDL preferred

Join Milestone to help residents stay engaged, active, and connected every day.

Milestone is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.