Assistant to the Head of School

Details

Posted: 03-Aug-26

Location: Boston, Massachusetts

Type: Full Time

Salary: $90,000- $125,000

Business Management

Assistant to the Head of School

Reports to:

Head of School

Department:
Head of School Office

Classification:
Non-Exempt, 12 month

The School is currently seeking a full-time Assistant to the Head of School. 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, supporting the smooth functioning of the school, and strategically utilizing the resources of the Head’s office. The Assistant supports the daily operation of the school, the work of the Board of Trustees, the strategic work of the administration, and the Associate Head of School’s calendar.

The Assistant to the Head of School coordinates, organizes, and performs administrative duties that require independent judgment, discretion, and confidentiality. Strong organizational and communication skills and a professional demeanor are essential to this high-profile position. Communication with trustees, faculty, administrators, parents, students, alumnae, and the public is frequent, making discretion, courtesy and diplomacy essential. This position models high standards for performance and ethical behavior, and remains calm in busy and high-pressure situations.

Detail-oriented, composed, and comfortable with multi-tasking, candidates should possess a positive outlook, collaborative work style, a high level of integrity and a strong work ethic. Candidates should possess a bachelor’s degree, and have 5+ years’ experience in relevant positions with significant responsibility. They should have the ability to assess, prioritize, and manage a range of requests, projects, and operations; to act in a supervisory role;

and to possess the personal skills to facilitate the smooth flow of work between departments. Candidates must be impeccable in their ability to handle confidential information and sensitive situations. Candidates should have facility with Google workspace and Microsoft Office applications, as well as Blackbaud or comparable programs.

This is a twelve-month position reporting to the Head of School.

• Manage the Head of School’s calendar, ensuring that her schedule reflects her priorities. Ensure that the Head is well prepared for meetings, events, travel, conferences, and external commitments.
• Prepare, organize, and manage materials for meetings, retreats, school events, and special projects connected to the Head of School Office.
• Field inquiries from 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 upcoming commitments and general whereabouts.
• Answer incoming calls for the Head, recording relevant information, responding where appropriate, or referring matters to the appropriate offices.

• Prepare and manage correspondence from the Head’s office, including information to be disseminated, announcements and correspondence for review and signature, and individual requests.
• Sort and triage correspondence to the Head and respond, where appropriate, as the representative for the Head.
• Partner with the Head in understanding the needs of the entire Winsor community, in order to solve problems, resolve conflicts, and find solutions whenever possible before matters require the Head’s attention, keeping the Head of School informed along the way.
• Maintain positive, professional, and effective working relationships with colleagues across departments to support the smooth flow of work between offices.

• Provide support to the Board of Trustees, including preparing materials and arranging logistics for board meetings; maintaining trustee contact information and committee lists; assisting with scheduling committee meetings; and preparing the BOT…