Senior Maintenance Supervisor (Multiple South Boston, MA Sites)

Senior Maintenance Supervisor (Multiple South Boston, MA Sites) Boston, MA, USA • Dorchester, Boston, MA, USA • Job Description Posted Tuesday, April 14, 2026 at 4:00 AM WinnCompanies is searching for a Senior Maintenance Supervisor to join our team and oversee 4 commercial units and 1,500 affordable residential units across Roxbury, Dorchester, Mattapan, and Jamaica Plain, MA. In this role, you will oversee the maintenance operations of multiple properties and perform maintenance functions as a working supervisor. Ensure that the physical condition of the property satisfies ownership and management objectives. Pay range for this position is $41.00 - $47.00 per hour, depending on experience. Select candidate will work Monday through Friday, 8:00 AM to 5:00 PM. Role requires on-call availability for emergencies. Responsibilities Lead and manage a maintenance staff at the properties on a day to day basis and act as a working Supervisor when not supervising staff. Assists in hiring, developing, training and holding staff accountable to operating standards. Conduct and participate in weekly staff meetings. Assist the Property Managers in controlling maintenance expenses. Responsible for preparing work schedules for maintenance staff and vendors to complete service requests, maintain the preventive maintenance program and overall curb appeal. Complete monthly building inspections and review third party property inspections to resolve maintenance repairs. Maintain working knowledge of all maintenance programs and capital improvement projects. Solicit bids from contractors with approval from the Property Manager and Regional Maintenance Manager. Participate in on call activity during off hours, emergencies and hands on maintenance activity. Requirements High school diploma or GED equivalent. 5-8 years of residential maintenance experience. 5+ years of supervisory and management experience. General knowledge of electrical, plumbing, appliance, and HVAC. A current driver's license in good standing and ability to meet the driving records standards outlined in the Company Safe Vehicular Operations Policy. Local travel is required with mileage reimbursement. Experience with computer systems such as Microsoft Office Suite. Past knowledge in bidding capital projects and supervising work. Prior experience using outside vendors / contractors in HVAC, electric, landscaping and painting. Ability to work independently with minimal supervision. Strong leadership capabilities with ability to guide teams. Solid verbal and written communication skills. Availability for on-call activity during off-hours for urgent needs. Ability to work with a diverse group of people and personalities. Preferred Qualifications Vocational or Technical training. CAMT (Certificate for Apartment Maintenance Technicians), and HVAC (Heating, Ventilation, and Air Conditioning) certifications. Benefits Generous time off policies (including 11 paid holidays (12 for MA employees); Generous Accrued Time Off increasing with years of service; Generous paid sick time; Annual day of service; Floating Holiday) 401(k) plan options with a company match Various Comprehensive Medical, Dental, & Vision plan options Flexible Spending Account, Dependent Care Flexible Spending Account, Health Savings Account options with HSA annual employer contribution Long Term Disability and voluntary Short Term Disability; Basic Term Life Insurance and AD&D; optional supplemental life insurance Health Expense Reimbursement program (including gym memberships, equipment, and subscriptions) Tuition Reimbursement program and continuous training and development opportunities Wellbeing program (group challenges, seminars, opportunities to earn points to reduce medical premiums), Employee Assistance Program, & Commuter and Parking Reimbursement options Employee Corporate Discount Programs Flexible and/or Hybrid schedules are available for certain roles Employee Relief Program supporting employees with unexpected hardships that place undue financial stress on them and their families 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. #J-18808-Ljbffr