Executive Director

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

The Executive Director leads the overall operations of the community, ensuring resident needs are met, regulatory compliance is maintained, and financial goals are achieved. This role oversees all departments, including resident care, dining, housekeeping, maintenance, and marketing, while providing strong leadership to the team.

What You’ll Do

• Lead and oversee all community operations, serving as the main point of contact for staff, residents, families, and community partners


• Supervise, coach, and mentor department leaders and team members


• Maintain high resident satisfaction and retention through quality service and proactive problem-solving


• Ensure compliance with local, state, and federal regulations


• Drive community occupancy and revenue through effective marketing and sales strategies


• Develop and manage annual operating and capital budgets


• Support staff hiring, training, performance management, and retention


• Oversee resident admissions, service plans, and healthcare management


• Foster a positive community culture aligned with Milestone’s values

What We’re Looking For

• Bachelor’s degree in Healthcare, Gerontology, Business, or related field preferred


• Minimum of 2–4 years of leadership experience in senior living or healthcare management


• Strong knowledge of regulatory requirements, budgeting, and operational management


• Excellent communication, interpersonal, and leadership skills


• Ability to manage multiple priorities and motivate a diverse team


• Passion for improving the lives of older adults and creating a thriving community

Join Milestone
Lead a dedicated team, make a meaningful impact in residents’ lives, and be part of a company that values care, community, and continuous growth.

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