Executive Assistant to the Head of School
Reports to: Head of School
Classification: Full-Time, Exempt, 12-Month Position
About Vermont Academy
Founded in 1876, Vermont Academy is an all-gender boarding and day school serving students in grades 9–12 and postgraduate. Nestled on 450 acres in the foothills of the Green Mountains in Saxtons River, Vermont, Vermont Academy is a community defined by opportunity, belonging, and transformation.
At Vermont Academy, students are challenged to discover who they are, who they want to become, and how they will contribute to the world around them. Through rigorous academics, exceptional athletic and arts programs, experiential learning, and a deep connection to the natural environment, Vermont Academy prepares students to lead lives of purpose and impact.
Our work is guided by four pillars: Community, Independence, Ingenuity, and Land. We believe that students thrive when they are known, challenged, supported, and inspired. We are equally committed to fostering a workplace where adults experience the same sense of belonging, purpose, and growth.
Diversity is a core value at Vermont Academy. We are passionate about building and sustaining an inclusive and equitable learning and working environment where all members of our community feel valued, respected, and empowered to contribute.
The Opportunity: What Will You Do & How Will We Partner?
Vermont Academy seeks an Executive Assistant to the Head of School to serve as a trusted operational partner and central coordinator for the Head’s Office. This is a highly relational, fast-paced role for someone who thrives on bringing order, clarity, and warmth to complex and dynamic work.
The Executive Assistant plays a central role in ensuring that the Head of School’s office operates with efficiency, responsiveness, and excellence. This role requires exceptional organizational skills, sound judgment, discretion, and the ability to manage multiple priorities with professionalism and grace.
At Vermont Academy, some of our most important work happens in the spaces between meetings, conversations, events, and decisions. The Executive Assistant helps ensure that this work is thoughtfully coordinated and effectively executed. From managing communications and scheduling to overseeing major institutional events and Board of Trustees meetings, this role helps create the conditions for strong leadership and healthy organizational functioning.
This position is ideal for someone who combines outstanding administrative ability with strong project management skills. The successful candidate will be equally comfortable managing calendars, coordinating complex events, communicating with diverse constituencies, and ensuring that important commitments move forward.
Your Core Responsibilities
This is a 12-month administrative position responsible for supporting the daily operations of the Head of School’s Office and coordinating key institutional meetings and events.
Support the Daily Work of the Head of School
Manage the Head of School’s calendar, meetings, travel, and correspondence.
Help prioritize commitments and protect time for high-impact work.
Prepare materials, background information, and logistics for meetings and engagements.
Manage communications entering and leaving the Head’s Office and help ensure timely, thoughtful follow-up.
Handle sensitive and confidential matters with professionalism and discretion.
Coordinate Board of Trustees Governance
Serve as the primary administrative liaison between the Head of School’s Office and the Board of Trustees.
Coordinate Board and Board Committee meetings, including scheduling, agendas, logistics, materials, and follow-up.
Prepare and distribute Board packets and supporting materials.
Maintain Trustee communications and governance records.
Support Board retreats and special governance initiatives.
Lead Major Institutional Events
Coordinate planning and execution for major institutional events, including:
Opening of School and Convocation
Board of Trustees Meetings and Retreats
Commencement / Graduation
Major donor and community events
Other special events as assigned
Develop event timelines, coordinate logistics, manage communications, and ensure strong execution
Support Project Management and Institutional Follow-Through
Track important deadlines, deliverables, and action items related to the Head’s priorities.
Help coordinate projects involving multiple departments and stakeholders.
Create systems that improve organization, communication, and follow-through across the Head’s Office
Support special initiatives and institutional priorities as assigned.
Qualifications
Bachelor's degree
Three or more years of progressively responsible experience in administration, project management, operations, communications, education, nonprofit leadership, or related fields.
Demonstrated success supporting senior leaders and managing complex projects.
Exceptional organizational, project management, and problem-solving skills.
Outstanding written and verbal communication abilities.
Strong technology skills, including Google Workspace and project management platforms.
Ability to manage multiple priorities simultaneously while maintaining attention to detail.
Experience working with boards, executive leaders, or governance structures preferred.
Independent school experience preferred but not required.
Personal Characteristics
The ideal candidate will be:
Strategic and solutions-oriented.
Highly organized and exceptionally reliable.
Warm, approachable, and relationship-centered.
Calm under pressure and adaptable in a fast-paced environment.
Trustworthy and capable of handling highly confidential matters.
Skilled at leading through relationships, influence, and trust rather than formal authority.
Committed to accountability, follow-through, and continuous improvement.
Intellectually curious and eager to learn.
Energized by the mission of independent school education and boarding school life.
Why Vermont Academy?
This is a unique opportunity to work alongside the Head of School, Senior Leadership Team, and Board of Trustees during a period of significant institutional momentum. Vermont Academy is investing in its future through enrollment growth, program innovation, campus improvements, strategic planning, and philanthropic engagement. The Executive Assistant to the Head of School will play a meaningful role in helping the Academy realize its ambitions while strengthening a community where students and adults alike have the room to become their best selves.
Vermont Academy is a school that values both ambition and humanity. We believe in healthy excellence, meaningful relationships, and the power of community to help young people become their best selves. The Executive Assistant to the Head of School will join a leadership team committed to strengthening a thriving school while honoring the traditions, values, and sense of belonging that have defined Vermont Academy for 150 years.
Salary Range
$45,000–$65,000, commensurate with experience.
To Apply
Please submit one PDF including:
Letter of interest, addressed to Head of School, Michael Peller
Current résumé
A list of three or more professional references with contact information (phone and email)
Send materials to mpeller@vermontacademy.org.