Director of Maintenance

Milestone Retirement; Stillwater (OK); On-site; USD 75,000 - 110,000; Full time

Benefits offered by this job

Medical, Dental, Vision (full-time)

401(k) with employer match

Generous PTO

Pet insurance

Perks at Work

Employee Assistance Program

Voluntary benefits options

Job summary

Milestone Retirement is seeking a Director of Maintenance to lead all maintenance, repair, and upkeep across our senior living communities. You’ll supervise maintenance and housekeeping staff, coordinate with vendors, and ensure safety, building, and regulatory compliance to provide safe, comfortable living spaces for residents.

Responsibilities include developing preventative maintenance programs, conducting quarterly walks, prioritizing work orders, and managing budgets.

Qualifications

• Experience leading maintenance teams in a senior living or multi-site setting.
• Ability to manage preventative maintenance programs and budgets.
• Strong knowledge of safety, building codes, and regulatory standards.

Responsibilities

• Develop and oversee preventative maintenance programs for HVAC, alarms, generators, and utilities.
• Supervise maintenance and housekeeping staff, plus vendor coordination.
• prioritize and close work orders while ensuring regulatory compliance.
• Inspect units for move-in readiness and oversee building exterior upkeep.
• Maintain inventory and supervise safety protocols for hazardous materials.
• Provide leadership, training, and performance feedback to staff.
• Respond to emergencies and maintain safe work environments.

Skills

Maintenance management

Supervisory experience

HVAC knowledge

Safety compliance

Communication skills

Education

High School Diploma or equivalent

Associate or Bachelor’s Degree in Business or related field

Tools

Microsoft Word

Microsoft Excel

Job description

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 experienced Director of Maintenance to lead all maintenance, repair, and upkeep activities across our communities. You’ll oversee maintenance and housekeeping staff, coordinate with vendors and contractors, and ensure compliance with safety, building, and regulatory standards. This role is essential to providing safe, well-maintained living spaces for our residents.

What You’ll Do

• Develop and maintain a preventative maintenance program for all community systems, including HVAC, fire alarms, generators, kitchen equipment, irrigation, and sprinklers


• Conduct quarterly property walk-throughs and coordinate with contractors and vendors to address maintenance needs


• Prioritize and complete work orders in compliance with company standards, resident satisfaction, and regulatory requirements


• Ensure compliance with local, state, and federal building codes, OSHA, EPA, SDS, and fire regulations


• Hire, coach, train, evaluate, and, if necessary, terminate maintenance and housekeeping staff


• Schedule and monitor staff labor within budget parameters


• Inspect apartments for move-in/move-out readiness, including patching, painting, and carpet cleaning


• Maintain the property exterior, landscaping, snow removal, and waste management


• Manage inventory of supplies, parts, and equipment


• Assess and repair plumbing, electrical, and other property issues within legal and safety standards


• Review safety data sheets (SDS) and implement precautions for hazardous chemicals


• Respond to resident or community emergencies as needed


• Maintain offices, shops, and mechanical areas according to company standards


• Promote a safe work environment and address unsafe actions


• Foster teamwork, assist beyond job responsibilities, and positively impact 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 in Business or related field strongly preferred


• Minimum three years of experience as maintenance staff; proven management experience required


• Valid State Driver’s License for vehicle travel


• Strong verbal and written communication skills


• Ability to evaluate staff performance, resolve conflicts, prioritize tasks, and work under pressure


• Experience with Microsoft Word and Excel preferred


• Compassion for and desire to work with older adults


• Knowledge of employment laws and company regulations


• Ability to perform physical tasks such as painting, vacuuming, climbing ladders, and accessing attics

Physical Requirements

• Ability to stand, walk, sit, use hands, reach, stoop, kneel, crouch, climb, and balance


• Ability to talk, hear, and use vision effectively


• Occasional weekend, evening, or night work and on-call as needed


• Possible exposure to chemicals, infectious hazards, and potential injury risks


• Ability to lift and move up to 50–100 lbs occasionally


• Frequent interaction with coworkers, residents, and vendors

Join Milestone to lead a skilled maintenance team, ensure safe and well-maintained living environments, and make a meaningful impact every day.

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