Senior Maintenance Supervisor (Village at Brookline)

WinnCompanies; Boston (MA); On-site; USD 52,000 - 65,000; Full time

Benefits offered by this job

Generous paid time off

Medical, dental, and vision coverage

401(k) with company match

Tuition reimbursement

Wellness programs

Flexible work options

Job summary

WinnCompanies is seeking a Senior Maintenance Supervisor to oversee maintenance across Village at Brookline and associated properties in Boston, MA. You will lead maintenance teams, perform hands-on tasks, and ensure safety, appearance, and maintenance standards meet ownership and Winn requirements.

Responsibilities include staffing, scheduling, inspections, budgeting, and coordinating with Property Managers. A strong background in electrical, plumbing, HVAC, and certificates is essential.

Qualifications

• High school diploma or GED equivalent.
• 5-8 years of experience in apartment, property, facilities, or building maintenance.
• 5+ years of supervisory and management experience.
• General knowledge of electrical, plumbing, appliance, and HVAC maintenance.
• Current driver's license in good standing and ability to meet driving standards.
• EPA certification.
• HVAC certification.
• Basic computer skills with web-based applications.
• Strong customer service, verbal and written communication skills.
• Strong supervisory and leadership skills.
• Availability for on-call activity during off-hours.

Responsibilities

• Lead and manage maintenance staff across assigned properties while serving as a hands-on working supervisor as needed.
• Assist with hiring, training, developing, and holding maintenance staff accountable to operating standards.
• Prepare maintenance staff and vendor schedules to complete service requests, preventive maintenance, unit upkeep, and curb appeal requirements.
• Conduct monthly building inspections, review third-party property inspections, and coordinate necessary maintenance repairs.
• Maintain working knowledge of maintenance programs and capital improvement projects, and assist Property Managers in controlling maintenance expenses.
• Solicit contractor bids with approval from the Property Manager and Regional Maintenance Manager.
• Participate in on-call and emergency maintenance during off-hours and perform hands-on maintenance activities as needed.

Skills

Supervisory experience

Leadership

Verbal and written communication

Customer service

Diversity and teamwork

Education

High school diploma or GED

Tools

Property management software

Job description

At WinnCompanies, our work starts with people — the residents who call our communities home, the neighborhoods we help strengthen, and the 4,600+ team members across 30 states, Washington, D.C., and Puerto Rico who make it all possible. As an award-winning owner, developer, and manager of high-impact, mixed‑income apartment communities, we are proud to be one of the nation’s leading managers of multifamily housing and one of the largest operators of affordable housing communities.

We bring together people who care about quality housing, meaningful service, and making a difference every day. Through our innovative resident services platform and commitment to exceptional communities, we offer career opportunities for individuals who want their work to create lasting impact.

Interested in learning more? Visit WinnCompanies to explore our benefits, mission, communities, and career opportunities.

About The Opportunity

WinnCompanies is searching for a Senior Maintenance Supervisor to join our team at Village at Brookline, a 193-unit affordable housing community located in Brookline, MA; The Residences at Brighton Marine, a 102-unit affordable housing community; and Oliver Lofts II, a 19-unit affordable housing community, where both properties are located in Boston, MA.

In this role, you will oversee maintenance operations across multiple properties while performing hands‑on maintenance functions as a working supervisor. You will lead maintenance teams and help ensure the physical condition, safety, appearance, and overall maintenance of the properties meet ownership, management, and Winn standards.

The pay range for this role is $38.00-$47.00 per hour. The selected candidate will adhere to the following schedule: Monday through Friday from 8:00AM to 5:00PM with the ability to work on‑call duty for emergencies.

Responsibilities

• Lead and manage maintenance staff across assigned properties while serving as a hands‑on working supervisor as needed.
• Assist with hiring, training, developing, and holding maintenance staff accountable to operating standards, and participate in weekly staff meetings.
• Prepare maintenance staff and vendor schedules to complete service requests, preventive maintenance, unit upkeep, and curb appeal requirements.
• Conduct monthly building inspections, review third‑party property inspections, and coordinate necessary maintenance repairs.
• Maintain working knowledge of maintenance programs and capital improvement projects, and assist Property Managers in controlling maintenance expenses.
• Solicit contractor bids with approval from the Property Manager and Regional Maintenance Manager.
• Participate in on‑call and emergency maintenance during off‑hours and perform hands‑on maintenance activities as needed.

Requirements

• High school diploma or GED equivalent.
• 5-8 years of experience in apartment, property, facilities, or building maintenance.
• 5+ years of supervisory and management experience.
• General knowledge of electrical, plumbing, appliance, and HVAC maintenance.
• Current driver's license in good standing and ability to meet the driving record standards outlined in the Company Safe Vehicular Operations Policy.
• Previous experience with REAC / NSPIRE inspections.
• Previous experience with capital improvement projects.
• EPA certification.
• HVAC certification.
• Basic computer skills with the ability to navigate web‑based applications.
• Strong customer service, verbal and written communication skills, with the ability to work effectively with diverse groups of people and personalities.
• Strong supervisory and leadership skills.
• Availability for on‑call activity during off‑hours to address urgent maintenance needs.

Preferred Qualifications

• Vocational or technical training.
• Certified Apartment Maintenance Technician (CAMT) and Heating, Ventilation, and Air Conditioning (HVAC) certifications.
• Previous experience with property management software.

Benefits & Perks

Eligible full‑time U.S. employees enjoy a competitive benefits package, including:

• Generous paid time off, paid holidays, sick time, a floating holiday, and a day of service
• Medical, dental, and vision coverage, plus HSA, FSA, and dependent care savings options
• 401(k) with company match and company‑paid life, AD&D, and long‑term disability insurance
• Tuition reimbursement, professional development opportunities, and career growth resources
• Wellness programs, employee assistance resources, commuter benefits, and employee discount programs
• Flexible work options for eligible positions

Learn more about our benefits at https://www.winnbenefits.com.

If you are a California Resident, please see our Notice of Collection here.

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors.