Executive Assistant to the Head of School

The Executive Assistant to the Head of School provides high-level executive, administrative, and operational support and serves as a trusted partner and key extension of the Head of School. This highly visible role requires exceptional discretion, sound judgment, initiative, professionalism, and organizational skill in managing complex priorities, confidential matters, executive logistics, and institutional relationships.

The Executive Assistant plays a central role in the effective operation of the Office of the Head of School and works closely with the Board of Trustees, Senior Leadership Team, faculty, staff, students, families, alumni, and external partners. In Taft's dynamic boarding school environment, the Executive Assistant manages the Head of School's calendar and travel, supports Board and governance activities, coordinates communications and events, oversees office operations and hospitality, and facilitates cross-functional collaboration.

The successful candidate will anticipate needs, exercise sound judgment, build trusted relationships, and ensure thoughtful communication and follow-through. The position supports the Head of School in carrying out established institutional priorities and facilitates effective coordination and communication across the Office of the Head of School and the broader School community.

Key Responsibilities

Responsibilities include, but are not limited to:

• Serve as a trusted partner and key extension of the Head of School, providing high-level administrative and operational support to facilitate the Head of School's priorities while exercising discretion and sound judgment in handling sensitive and confidential matters.
• Manage the Head of School's complex calendar, correspondence, appointments, commitments, and related logistics, ensuring the Head of School's time is thoughtfully aligned with institutional priorities. Coordinate professional and personal appointments and logistical needs for the Head of School and spouse, as appropriate.
• Coordinate executive travel arrangements for the Head of School, including flights, accommodations, ground transportation, itineraries, and related logistics.
• Oversee the day-to-day operations, budget, and resource management of the Office of the Head of School, including the procurement of books, supplies, materials, and other resources necessary for its effective operation.
• Prepare, draft, edit, and coordinate communications, speeches, presentations, recommendation letters, and correspondence on behalf of the Head of School, maintaining consistency of voice and alignment with the School's mission and values.
• Partner with the Head of School and Board Chair to support effective Board governance, including the preparation and distribution of agendas, meeting materials, minutes, and related communications; maintenance of governance records; and coordination of bylaw updates and other governance requirements.
• Partner with the Alumni Office and other colleagues, as appropriate, to plan and execute governance activities and leadership engagements, including Trustees' Weekends, Board retreats, committee meetings, and other events involving the Head of School.
• Coordinate meeting and event logistics for the Head of School, including reserving and preparing appropriate spaces, arranging facilities and resources, and ensuring logistical details are addressed in advance.
• Oversee hospitality and the guest experience for the Office of the Head of School, including coordinating appropriate gifts and expressions of appreciation for visiting speakers, Trustees, special guests, and other key stakeholders.
• Support the planning and execution of Commencement, graduation-related activities, and school-wide awards and recognition programs in collaboration with appropriate departments and stakeholders.
• In collaboration with the Senior Advisor to the Head of School, support continuity within the Office of the Head of School during the Head of School's absence by coordinating communications, meetings, materials, and appropriate follow-through.
• Provide high-level administrative and organizational support to the Senior Leadership Team, coordinating meetings, materials, communications, and follow-up in support of established school-wide priorities and initiatives.
• Facilitate the effective flow of information across the School by coordinating documents, communications, and information-sharing among the Business Office, Registrar, Advancement, Admissions, Human Resources, Information Technology, and other departments.
• Anticipate the information, materials, and resources needed by the Head of School, ensuring timely access to relevant updates, data, and context to support informed decision-making.
• Collaborate with colleagues across the School on complex and confidential institutional processes, including communications, scheduling, admissions-related activities, travel, database management, and other initiatives involving the Office of the Head of School.
• Partner with the Advancement Office and Director of Special Events to plan and execute events and engagements hosted by the Head of School, ensuring thoughtful and seamless coordination.
• Serve as a primary point of coordination with accreditation and membership organizations, including NEASC, CAIS, TABS, and NAIS, as well as other external organizations, professional associations, vendors, and partners.
• Support the onboarding, orientation, scheduling, and ongoing administrative needs of new Trustees and ACMs, providing a thoughtful introduction to the School's leadership structure, governance practices, and institutional priorities.
• Build and maintain trusted relationships with faculty, staff, students, parents and guardians, alumni, Trustees, and external stakeholders, serving as a professional and welcoming representative of the Office of the Head of School.
• Anticipate emerging needs and challenges, proactively addressing administrative and operational issues and facilitating timely follow-through on behalf of the Head of School.

Qualifications

• Bachelor's degree preferred; an equivalent combination of education and relevant professional experience will be considered.
• Five or more years of relevant experience providing executive-level administrative support or working in institutional governance, preferably in an educational, nonprofit, or similarly complex organization.
• Demonstrated ability to manage confidential and sensitive information with discretion, integrity, and sound judgment.
• Proven ability to independently manage complex calendars, projects, logistics, and competing priorities.
• Exceptional written, verbal, and interpersonal communication skills and the ability to communicate effectively with a wide range of constituencies.
• Strong technology skills, including proficiency with Google Workspace and Microsoft Office. Experience with platforms such as BoardEffect, Veracross, Blackbaud, Doodle, and SurveyMonkey is preferred.
• Experience supporting a Board of Trustees, senior leadership team, or executive leader strongly preferred.
• Demonstrated ability to collaborate effectively in a dynamic environment where priorities may shift quickly.