Executive Assistant to Head of School; Leave Coverage Temporary Position

Position: Executive Assistant to the Head of School (Leave Coverage) Full-Time Temporary Position | July - November 2026
Location: Pomfret

Job Type

Temporary

Description

We are seeking a highly organized, proactive, and detail-oriented Executive Assistant to provide maternity leave coverage for the Head of School office in a fast-paced independent school environment. This temporary full-time position will run from July through approximately November 2026 and plays a critical role in supporting senior leadership, coordinating board and committee operations, managing communications, and overseeing a wide range of administrative projects and events.

The ideal candidate enjoys working in a community that requires adaptability, professionalism, and is comfortable managing multiple priorities while maintaining exceptional attention to detail and discretion. Temporary employees are given serious consideration for full-time roles when they become available.

About the Role

This position serves as a trusted partner to senior leadership, managing daily operations, board and committee coordination, communications, and a range of administrative projects and events. No two days look the same, and that is part of what makes this work engaging. For the right person, this temporary role is a meaningful opportunity to contribute at the highest level of an exceptional school community.

Requirements

Executive & Administrative Support

• Manage complex calendars for senior leadership, including frequent scheduling changes and competing priorities
• Coordinate and schedule internal and external meetings
• Monitor executive schedules and ensure leadership remains on track throughout the day
• Arrange travel, lodging, conference registrations, and itineraries for executive leadership

Meeting & Committee Coordination

• Coordinate leadership group meetings
• Prepare agendas in collaboration with leadership team members
• Send weekly agenda surveys and collect meeting materials
• Take detailed meeting minutes and distribute action items
• Maintain records and supporting documentation for meetings

Board of Trustees Support

• Serve as the primary administrative contact for Board of Trustees matters
• Coordinate board meeting logistics including meeting space, food service, Zoom setup, and materials
• Organize presentations, pre-read documents, and board packets
• Upload and maintain materials within the OnBoard platform
• Communicate regularly with board members regarding attendance, logistics, and questions
• Take and publish formal board meeting minutes

Communications & Publications

• Produce and distribute weekly employee newsletters
• Create and distribute monthly summer newsletters
• Coordinate newsletter submissions and executive messaging
• Assist with holiday card artwork/photo coordination and mailing list management
• Manage communications related to events, faculty meetings, and evaluations

Event & Operations Coordination

• Support planning and execution of Arrival/Opening Days activities
• Coordinate late arrival processes, key management, and required documentation tracking
• Submit event holds and coordinate scheduling through Events Manager
• Organize faculty treats, exam week snacks, and other hospitality items
• Coordinate recurring food orders and meeting refreshments
• Assist with faculty/staff name tag ordering and employee updates

Employee & Faculty Support

• Schedule and coordinate Stay Meetings
• Manage onboarding-related administrative tasks for new employees
• Coordinate faculty evaluation communications
• Support school scheduling updates and reminders

Qualifications

• Prior executive assistant, administrative, or operations experience required
• Exceptional organizational and time-management skills
• Ability to manage confidential information with discretion
• Strong written and verbal communication skills
• Experience supporting senior leadership and/or boards preferred
• Ability to multitask and adapt quickly in a dynamic environment
• Proficiency with Microsoft Office, Google Workspace, and virtual meeting platforms
• Experience with scheduling software and document management systems preferred

Preferred Qualifications

• Independent school or nonprofit experience preferred
• Experience coordinating events and board meetings
• Strong attention to detail and follow-through
• Ability to work collaboratively across multiple departments and stakeholders

Schedule & Term

• F…