Assistant Director of Facilities

The Winsor School
Boston, MA

Founded in 1886, The Winsor School is an independent girls’ school for academically promising and motivated students in grades five through twelve. Located in the heart of Boston’s Longwood Medical and Academic Research area, our students benefit from the school's longstanding commitment to providing a superior education for girls, inspirational and dedicated faculty, and diverse and talented community. Winsor strives to consciously create an environment of respect and inclusion and to support ethnic, racial, religious and socio-economic diversity among all the constituencies of the school. Winsor supports this commitment through its inclusive curriculum, success addressing a range of learning styles, availability of a wide array of diversity efforts and programs, and participating in the greater Boston community.





The Winsor School is an independent girls' school for academically promising and motivated students in grades five through twelve , located in Boston’s Longwood/Fenway area. Founded in 1886 by Mary Pickard Winsor, it began as a small school of eight girls and has grown over more than a century into a vibrant, city-centered institution drawing students from throughout the Greater Boston region.

Job Description : Assistant Director of Facilities
Reports to : Director of Facilities
Department : Business Office
Classification : Exempt,12 month

Position Summary
The Assistant Director of Facilities reports to the Director of Facilities and assists in the oversight of the school’s facilities operations, construction, physical plant, janitorial, fleet vehicles, and event operations, including maintenance of all buildings and grounds, athletic fields, vehicles, and other areas. This position, when assigned, will assume the responsibility of the Director of Facilities in the Director’s absence.

This is a twelve-month exempt position reporting to the Director of Facilities.
Essential Functions
  • Supervise and confer with facilities personnel regarding proper methods, procedures and equipment requirements. Ensure appropriate response to users requests and needs
  • Supervise procurement and usage of supplies
  • Participate in the development and administration of annual operating budgets and be responsible for maintaining limitations
  • Review construction project and maintenance cost estimates and scope
  • Ensure that carpentry, plumbing, HVAC and electrical work is accomplished in a timely manner. Inspect completed work
  • Ensure that all preventive maintenance is performed as scheduled
In Conjunction with the Director of Facilities
Coordinate with staff as necessary to comply with state and federal regulations
  • Assist in the evaluation and selection of new equipment and building/energy management systems and other campus improvement efforts
  • Assist in planning for present and future use of existing facilities
    • Review architectural/mechanical drawings for errors, omissions, problems, and design changes to correct and improve
  • Inspect buildings and utility distribution systems
  • Identify maintenance and repair requirements, and prepare work requests to accomplish work
  • Design, or redesign, assigned projects to improve quality of work and meet the needs of instructional or administrative staff
  • Manage all aspects of snow and ice removal operations, including pre-storm planning, vendor coordination, equipment readiness, and post-storm cleanup to maintain safe campus access and minimize operational disruption.
Other Responsibilities
  • Recommend policy, personnel, and procedural changes
  • Attends mandatory meetings, including, but not limited to, opening and closing meetings, faculty/staff meetings, division meetings, and department meetings as required by Chief Operating Officer
  • Attends assemblies and community time meetings as required by Chief Operating Officer
  • Perform related duties as assigned by the Director of Facilities
Required Qualifications
  • High School degree required.
  • Strong mechanical acumen and a minimum of seven (7) years of trades experience which may include HVAC, Electrical, Plumbing and Carpentry
  • Minimum of seven years of facilities maintenance and operations experience, including project and program budget administration, contract administration, and employee supervision.
  • Engineering or Construction Management degree preferred; equivalent combination of education, training, and experience will be considered.
  • Demonstrated success working with individuals from diverse backgrounds and cultures.
  • Comprehensive knowledge of maintenance and preventive methods for buildings, utility systems, and physical structures; building construction methods and materials; budgeting and fiscal management; program planning and scheduling; estimating practices; bid specification development; contract negotiation and administration; and generally accepted construction principles and safety regulations ideally within a school environment.
  • Working knowledge of Uniform Building Code (UBC), ADA, OSHA, Workers’ Compensation, hazardous materials control, and other applicable city, state, and federal regulations.
  • Strong leadership and supervisory skills, including the ability to train, assign, evaluate, and develop staff.
  • Excellent organizational, communication (oral and written), and problem-solving skills, including the ability to write complex proposals, manage sensitive issues, resolve conflicts, and work effectively with students, staff, faculty, and administrators.
  • Handles confidential information in accordance with school policies, HIPPA-related considerations and employment law.
  • Appropriate personal and professional boundaries
  • A demonstrated commitment to community and inclusion work
  • Must be willing and able to work a flexible schedule based on weather conditions and school event needs, including morning, afternoon, evening, weekend, and holiday hours; work during inclement weather; and serve in an on-call capacity as required, up to 24 hours per day.
  • Must have a valid state driver’s license
Preferred Qualifications and Skills
  • Massachusetts Unrestricted Construction Supervisor’s License
  • Proficiency in construction and maintenance management software and strong computer literacy, including Microsoft Office and facilities/project management systems (e.g., SchoolDude).
  • Demonstrated project management expertise, including preparing and interpreting plans and specifications; accurately estimating project and maintenance costs; assisting in managing major construction and renovation projects; and developing short- and long-range strategic plans.
Work Environment and Physical Demands
The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
  • While performing the duties of this job, the employee is frequently required to walk, stand, sit and talk or hear. The employee is occasionally required to use hands to handle, feel or operate objects, tools, or controls; and reach with hands and arms. The employee is occasionally required to climb or balance; stoop, kneel, crouch, or crawl.
  • Ability to perform multiple concurrent tasks and function in a fast-paced working environment
  • The employee must frequently lift and/or move up to 50 pounds. Specific vision abilities required by this job include close vision, color vision, and the ability to adjust focus.
Nothing in this Job Description restricts Winsor’s right to assign or reassign duties and responsibilities to this position at any time.

Salary Range: $85,000 - $120,000
Posted 2026-04-07

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