Executive Assistant to the Head of School (Leave Coverage) Full-Time Temporary Position | July – November 2026 in Pomfret, Connecticut at Pomfret School Incorporated

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.

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.

• 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

• 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

• 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

• 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

• 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

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

• 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

• 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

• Full-time temporary position
• Coverage period: July through approximately November 2026
• Occasional early mornings and event support may be required

You are organized and proactive, but you lead with warmth. You handle shifting priorities without losing your footing, and you understand that in a school community, how you make people feel matters as much as what you accomplish. You bring sound judgment, a collaborative spirit, genuine appreciation for the rhythms of independent school life, and the discretion that senior leadership work requires.

Work Conditions:

• Works in an in-person environment dealing with a wide variety of challenges, deadlines, and a varied and diverse array of contacts
• May work at a desk and computer for extended periods of time

Even in a temporary capacity, you will be welcomed as a full member of our team, supported throughout your time here, and part of a community that takes genuine care of its people and recognizes what each one brings. Pomfret School is a close-knit boarding and day school community in northeastern Connecticut where relationships are at the center of everything we do. We believe in recognizing the unique gifts of every individual, and we are seeking an Executive Assistant who embodies that same spirit: someone who will keep the Head of School’s office running smoothly while showing up as a genuine member of our community.