Assistant to the Head of School

Staff / Full-Time

The Winsor School, Boston, MA

The School is currently seeking a full-time Assistant to the Head of School, starting in summer
2022. The Assistant to the Head of School acts as chief of staff of the Head’s office, providing
executive level administrative support to the Head, facilitating the smooth functioning of the
school, and strategically utilizing the resources of the Head’s office. The Assistant to the Head of
School coordinates, organizes, and performs administrative duties that require independent
judgment, discretion, and confidentiality. 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.

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. Utmost discretion, courtesy and diplomacy are essential. This
position models high standards for performance and ethical behavior.

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. State of the art computer
skills are required, including facility with Google applications and Blackbaud, or comparable
programs. 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

Job responsibilities include:

  • Manage the Head’s calendar, to ensure that her schedule reflects her priorities. Have materials prepared for each meeting; field inquiries from and arrange meetings with staff, faculty, direct reports, parents, and guests; schedule administrative meetings and retreats; organize the Head’s travel and conferences; support the Head’s service in external educational roles.
  • Manage the flow of the Head’s day, including keeping meetings on schedule, greeting visitors, knowing Head’s upcoming events and general whereabouts.
  • 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.
  • 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 the Head needs to address them.
  • 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.
  • Answer incoming calls for the Head, recording relevant information to assist her in responding to calls, or refer calls to the appropriate employee.
  • Manage the Associate Head of School’s calendar.
  • Provide support to the Board of Trustees, including preparing materials and arranging logistics for board meetings; maintaining BOT contact information and committee lists; assist with scheduling committee meetings; prepare BOT calendar.
  • 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 duties as assigned.

The Winsor School

Boston, MA
Elementary, Middle School, High School