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Executive Assistant to Head of School

Job in Litchfield, Litchfield County, Connecticut, 06759, USA
Listing for: National Association of Independent Schools
Full Time position
Listed on 2026-01-04
Job specializations:
  • Administrative/Clerical
    Education Administration, Administrative Management
  • Education / Teaching
    Education Administration
Salary/Wage Range or Industry Benchmark: 55000 - 75000 USD Yearly USD 55000.00 75000.00 YEAR
Job Description & How to Apply Below
Position: Executive Assistant to the Head of School

Executive Assistant to the Head of School

Immediate Opening

Reports To:

Head of School, 12-month position

Position Overview

The Executive Assistant to the Head of School plays a vital role in the smooth and effective functioning of the Head’s Office. This individual is responsible for a wide range of administrative and operational support duties and serves as a key point of contact for internal and external stakeholders. The Executive Assistant also provides essential support to the Board of Trustees and the Associate Head of School.

The ideal candidate will be highly organized, proactive, diplomatic, and able to manage multiple priorities with discretion and professionalism.

Forman’s Mission, Promise, and Core Values

Forman School is an independent, coeducational, college preparatory school for boarding and day students with identified learning differences. Forman develops the whole student, based on each individual’s learning profile, so that all graduates become educated, confident self‑advocates throughout life.

Forman is committed to sustaining an inclusive environment that fosters a deeper understanding of differences in race, gender, sexual orientation, age, ethnicity, religion, socioeconomic status, geographical origin, physical ability, and family structure.

We believe society is bettered when we learn from and embrace those with different experiences and perspectives from our own. Our community values truth, respect, and kindness.

Key Responsibilities
  • Head of School Support
    • Manage the Head of School’s calendar, appointments, travel arrangements, and correspondence.
    • Act as the primary liaison between the Head of School and faculty, staff, parents, students, and external partners.
    • Prepare and edit reports, presentations, communications, and other documents on behalf of the Head of School.
    • Organize and coordinate logistics for school events hosted by or involving the Head of School.
    • Maintain confidential files and sensitive information with discretion and integrity.
  • Board of Trustees Support
    • Coordinate all logistics for Board of Trustees meetings, retreats, and events, including scheduling, room setup, materials preparation, and catering.
    • Record, transcribe, and distribute meeting minutes and other official documentation.
    • Serve as the point of contact for Board members, ensuring timely communication and follow‑up on action items.
    • Maintain the Board portal and ensure accurate record‑keeping of Board policies, minutes, and governance documents.
  • Support to the Associate Head of School
    • Provide administrative and logistical support to the Associate Head, including scheduling, project management, and communications.
    • Serve as a liaison to faculty and staff on matters requiring input or attention from the Associate Head.
  • Administrator on Duty (AOD) Responsibilities
    • Serve as Administrator on Duty on a rotating basis, including evenings and weekends as scheduled.
    • Ensure campus safety and respond to incidents, emergencies, or student issues in collaboration with residential life and security staff.
    • Communicate effectively with students, faculty, staff, and parents during AOD shifts, documenting any notable occurrences.
    • Support a positive, safe, and inclusive campus environment during all AOD responsibilities.
Community Support
  • Serve as a central hub for internal communication by managing daily school‑wide messaging, calendars, and logistical planning tools to ensure clarity and alignment across all departments.
  • Oversee the development, communication, and maintenance of institutional calendars, including the academic and events calendar, faculty and student planners, and conference room scheduling.
  • Lead the planning and execution of major school events such as Commencement, student registration, and Family Weekends, in collaboration with school leadership and key departments.
  • Coordinate logistical and operational support for school-wide initiatives and events, including academic programs and Advancement‑related engagements.
  • Maintain oversight of institutional documentation, including internal drives and handbooks, ensuring timely updates and consistent communication of policies.
  • Partner with colleagues across departments to…
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