Assistant to the Head of 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, 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.

Assistant to the Head of School

Reports to: Head of School 

Department: Head of School Office

Classification: Non-Exempt, 12 month

Position Summary

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. 

Essential Functions 

Executive Support and Office Coordination 

• 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.

Communications

• 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.

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 committee lists; assisting with scheduling committee meetings; and preparing the BOT calendar. Collaborate with the Advancement office on BOT support where necessary.

• Support the strategic work of the Administrative Council and other leadership groups by preparing materials, coordinating logistics, tracking follow-up items, and helping organize meetings and retreats. 

• Manage the Associate Head of School’s calendar and coordinate scheduling as needed to support the work of the Head of School Office.

• Assist with and/or lead occasional projects and larger events involving many constituents, including support during summer projects, the hiring season, commencement, and the opening of school.

• Manage the Head’s budget and reimbursements; manage office budget and order supplies.

• Perform routine office work, including filing, record retention and maintenance, and maintain the highest standards of confidentiality in record-keeping.

Other Responsibilities

• Attends mandatory meetings, including, but not limited to, opening and closing meetings, faculty/staff meetings, assemblies, and Operations Committee meetings, as required.

• Supports and attends board, advancement, and school events as requested by the Head of School.

• Is involved in the daily life, community, and programs of the school.

• Performs other duties as assigned by the Head of School.

Required Qualifications

• Bachelor’s degree.

• Five or more years of experience in relevant administrative positions supporting senior leadership.

• Excellent written and verbal communication skills and 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

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 established deadlines.

• Proactive, self-directed, and reliable, demonstrating initiative and following tasks and assignments 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 and calm tone for the community.

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.

Nothing in this Job Description restricts Winsor’s right to assign or reassign duties and responsibilities to this position at any time.

Compensation and Benefits

1. This is a full-time, benefits-eligible position with an anticipated salary range of $90,000 to $125,000 , commensurate with experience and qualifications. The role also offers the opportunity to work in a mission-driven school environment and make a meaningful impact.