Assistant to Head of School and Board of Trustees

Assistant to the Head of School and Board of Trustees

• Position Type:
  Administration/ Assistant to the Head of School & Board of Trustees
• Date Posted: 5/6/2026
• Location:
  
  Winchester Thurston – City Campus
• Job Classification:
  Administrative, Non‑exempt, Salary
• FT/PT Status:
  Full‑Time
• Work Schedule:
  
  Monday-Friday, 8a-4p, occasional evenings and weekends required
• Department:
  Administrative, Head of School

Winchester Thurston School seeks an experienced executive assistant who will provide comprehensive, confidential, and professional administrative support to the Head of School and the School’s Board of Trustees, and is responsible for the overall management of the Office of the Head of School.

The Assistant to the Head of School reports directly to the Head of School and works collaboratively with trustees, administrators, faculty, staff, students, and families to advance the School’s Mission.

• Serve as the office manager for the Head of School’s Office and manage the Head of School’s daily schedule and arrange meetings, as required
• Serve as the assistant to the Board of Trustees by taking minutes at Board meetings, arranging committee meetings, and serving as the communication link among Trustees, sending reminders, and coordinating materials for Board meetings and the annual Board of Trustees bio book
• Be present at the start of meetings to ensure that food, beverages, copies of appropriate documents, and technology are prepared
• Serve as the Head of School’s representative when visitors or prospective employees arrive; arrange transportation, schedules and guide them through transitions throughout the day
• Anticipate upcoming meetings of the Head and prepare appropriate documents or files
• Initiate and schedule a weekly meeting with the Head of School to arrange priorities
• Communicate with the Head prior to communicating with Trustees or other important constituents
• Draft and/or edit, as requested, written communication from the Head to ensure there are no typos, misspellings, grammatical or content errors
• Coordinate vacation schedule with the Head to ensure consistent coverage of the Head’s Office
• Analyze practices such as record‑keeping systems, forms control, and office layout, creating new systems or revising established procedures to maximize efficiency
• Locate and compile information and format reports, graphs, tables, records and other sources of information using various software applications
• Use various software applications, such as spreadsheets, relational databases, statistical packages and graphics packages to assemble, manipulate and/or format data and/or reports
• Arrange travel for the Head of School and other administrators, as requested
• Manage all expenses for the Head of School’s budget as well as the office budget and reconcile monthly charges on the Head of School’s credit card account
• Reserve rooms and make food service, room set‑up and audiovisual arrangements for all meetings
• Other duties as assigned

• Experience in an executive assistant role, preferably in an educational or nonprofit setting
• Excellent organizational, interpersonal, and communication skills
• Proficiency in Microsoft Word and Google Suite applications as well as general aptitude for learning new applications and software
• Ability to manage multiple priorities and adapt to changing situations and schedules
• Ability to maintain professionalism and confidentiality
• Experience liaising with multiple stakeholder groups such as Trustees, students, parents, employees, vendors, etc.

• Robust and low‑cost health, dental, vision benefits
• Ample PTO and sick‑time offered to support work‑life balance
• Professional development
• Retirement plan with generous employer contribution
• Other benefits include: discounted lunch, free parking, life insurance, EAP, FSA, dependent‑care FSA, summer camp discounts

Winchester Thurston School is an equal opportunity employer. WT is dedicated to the goal of building a culturally diverse and pluralistic community and strongly encourages applications from people of color, LGBTQ+ candidates, and women.