Assistant to the Head of School

Location: Boston, Massachusetts | Type: Full Time | Salary: $90,000 - $125,000

About the Role

The Assistant to the Head of School provides executive-level administrative support to the Head, serving as the welcoming presence in the Head of School’s office and supporting the smooth functioning of the school. This role strategically utilizes the resources of the Head’s office to support the daily operation of the school, the work of the Board of Trustees, the strategic initiatives of the administration, and the Associate Head of School’s calendar. The Assistant coordinates, organizes, and performs administrative duties requiring independent judgment, discretion, and confidentiality. Strong organizational and communication skills, along with a professional demeanor, are essential for this high-profile position.

Frequent communication with trustees, faculty, administrators, parents, students, alumnae, and the public demands discretion, courtesy, and diplomacy. This position models high standards for performance and ethical behavior while remaining calm in busy and high-pressure situations.

Responsibilities

• Executive Support and Office Coordination
  • Manage the Head of School’s calendar, ensuring alignment with her priorities.
  • Prepare the Head for meetings, events, travel, conferences, and external commitments.
  • Organize and manage materials for meetings, retreats, school events, and special projects.
  • Field inquiries and arrange meetings with staff, faculty, direct reports, parents, trustees, guests, and external partners, using sound judgment to determine appropriate next steps.
  • Manage the flow of the Head’s day, including keeping meetings on schedule, greeting visitors, anticipating needs, and maintaining awareness of the Head’s commitments.
  • Answer incoming calls for the Head, recording relevant information, responding where appropriate, or referring matters to the appropriate offices.
• Communications
  • Prepare and manage correspondence from the Head’s office, including announcements, information dissemination, and individual requests for review and signature.
  • Sort and triage correspondence to the Head, responding as the representative where appropriate.
  • Partner with the Head to address community needs, resolve conflicts, and find solutions before matters require the Head’s attention.
  • Maintain positive, professional, and effective working relationships with colleagues across departments.
• Board, Administrative, and Project Support
  • Provide support to the Board of Trustees, including preparing materials and arranging logistics for board meetings, maintaining trustee contact information, and assisting with committee meetings.
  • Collaborate with the Advancement office on Board of Trustees support.
  • Support the strategic work of the Administrative Council and other leadership groups by preparing materials, coordinating logistics, and tracking follow-up items.
  • Manage the Associate Head of School’s calendar and coordinate scheduling as needed.
  • Assist with or lead occasional projects and larger events, including summer projects, hiring season, commencement, and the opening of school.
  • Manage the Head’s budget and reimbursements, as well as the office budget and supply orders.
  • Perform routine office work, including filing, record retention, and maintaining confidentiality in record-keeping.
• Other Responsibilities
  • Attend mandatory meetings, including opening and closing meetings, faculty/staff meetings, assemblies, and Operations Committee meetings.
  • Support and attend board, advancement, and school events as requested by the Head of School.
  • Engage in the daily life, community, and programs of the school.
  • Perform other duties as assigned by the Head of School.

Requirements

• Bachelor’s degree.
• Five or more years of experience in relevant administrative positions supporting senior leadership.
• Excellent written and verbal communication skills, with the ability to represent the Head of School Office with professionalism, warmth, and discretion.
• Demonstrated ability to assess, prioritize, and manage a range of requests, projects, and operations in a fast-paced environment.
• Impeccable judgment in handling confidential information and sensitive situations.
• Strong proficiency with Google Workspace, Microsoft Office, Blackbaud or comparable school databases, and calendar and project-management tools.
• Appropriate personal and professional boundaries.
• A demonstrated commitment to community and inclusion work.

Work Environment and Physical Demands

• Frequent talking, listening, walking, sitting, and standing.
• Ability to perform multiple concurrent tasks and function in a fast-paced working environment.
• Occasional evening or weekend commitments may be required for board meetings, school events, or other institutional priorities.

Preferred Qualifications and Skills

• Experience supporting a head of school, chief executive, board, or senior leadership team in an independent school, nonprofit, or similarly complex organization.
• Experience coordinating board or committee materials, calendars, minutes, and logistics.
• Excellent planning, organization, problem-solving, and attention to detail, with the ability to multitask, prioritize, and meet deadlines.
• Proactive, self-directed, and reliable, demonstrating initiative and following tasks through to completion.
• Effective collaborator and relationship builder who maintains positive working relationships and resolves issues with care and professionalism.
• Innovative and adaptable, using technology and creative thinking to improve processes and support successful project completion.
• Ability to project calm in busy and stressful times, setting a positive tone for the community.

About The Winsor School

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, Winsor benefits from a longstanding commitment to providing a superior education for girls, inspirational and dedicated faculty, and a diverse and talented community. Winsor strives to create an environment of respect and inclusion, supporting ethnic, racial, religious, and socio-economic diversity among all constituencies. This commitment is reflected in the inclusive curriculum, efforts to address a range of learning styles, and participation in the greater Boston community.