Assistant to the Head of School
  • Administrative
  • Head of School

The Winsor School, Boston, MA

Accredited by NEASC

The Winsor School is an independent girls' school for academically promising and motivated students in grades five through twelve. Our diverse, vibrant community values intellectual curiosity, authentic engagement, and personal integrity and prepares young women to pursue their aspirations and contribute to the world. Winsor strives to create an environment of respect and inclusion.

The School is currently seeking a full-time Assistant to the Head of School, starting in June 2021. 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, and 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. 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 ethic. 

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. 
  • 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. 
  • Perform routine office work, including filing, record retention and maintenance, and maintain the highest standards of confidentiality in record-keeping. 
  • Manage the Head’s budget and reimbursements; manage office budget and order supplies.
  • As needed, assist other administrative offices with occasional projects and larger events involving many constituents, including support during summer projects, the hiring season, commencement, and the opening of school.
  • Other duties as assigned. 

Please visit the Winsor Careers page to apply and submit your resume, and a cover letter: