Executive Assistant to the President & Head of School

Job Overview
Massanutten Military Academy, a private, nonprofit, college preparatory boarding school, seeks a highly professional and mission-driven Executive Assistant to support the President & Head of School.

Operating within a structured, boarding school environment, this position serves as a key member of the Head of School’s command support staff. The Executive Assistant ensures efficient execution of leadership priorities, maintains strict confidentiality, assists with planning, and supports communications across the Academy’s chain of command.

The ideal candidate demonstrates exceptional organizational ability, discretion, adaptability, and respect for the Academy’s traditions, discipline, and leadership model.

Responsibilities

Executive & Command-Level Support

• Manage and prioritize the President & Head of School’s calendar in alignment with institutional priorities
• Coordinate meetings, travel, and official engagements
• Prepare executive briefings, reports, correspondence, and presentations
• Serve as gatekeeper for incoming communications, exercising sound judgment and discretion
• Ensure timely follow-up on directives issued by the President through the chain of command

Board of Trustees & Governance Support

• Coordinate all Board of Trustees meetings, committees, and official functions
• Prepare Board packets, agendas, and maintain official minutes and records
• Ensure governance documentation aligns with nonprofit best practices
• Maintain secure and confidential Board records

School Operations & Communication

• Serve as liaison between the President and Academy leadership, including academics, admissions, advancement, athletics, student affairs, and other administrative departments
• Support communication flow consistent with school structure, protocol, and chain of command
• Assist in drafting official Academy communications, orders, and announcements
• Maintain awareness of Academy schedules, formations, ceremonies, and command activities

Event & Institutional Coordination

• Coordinate high-level events including parades, ceremonies, VIP visits, graduations, and alumni functions
• Assist with logistics for command staff meetings and Academy-wide events
• Represent the President’s Office with professionalism during official functions

Administrative & Office Management

• Maintain confidential records, files, and sensitive personnel or student information
• Oversee daily operations of the President’s Office
• Track strategic initiatives, deadlines, and institutional priorities
• Ensure efficient administrative processes and workflow

Skills

• Extensive experience in executive administrative support with strong organizational skills.
• Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint), Google Workspace (Gmail, Docs, Sheets), and office management software such as DocuSign, Zoom, Microsoft Teams.
• Exceptional typing speed combined with transcription and proofreading abilities to produce accurate documents swiftly.
• Demonstrated ability to manage multiple projects simultaneously while maintaining attention to detail.
• Excellent communication skills—both verbal and written—with professional phone etiquette across multi-line phone systems.
• Professional judgement and discretion
• Experience with calendar management tools like Microsoft Outlook Calendar; familiarity with office technology including multi-line phones and data entry systems. This role is perfect for an energetic individual eager to support leadership in a vibrant educational setting while advancing their administrative career through meaningful responsibilities. Join us in creating an organized environment that empowers our school community to thrive!

Qualifications

Required

• Bachelor’s degree preferred. Equivalent experience considered
• Minimum of two (2) years of executive administrative support experience
• Exceptional organizational, time management, and multitasking abilities
• Strong written and verbal communication skills
• Demonstrated ability to maintain strict confidentiality
• Proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint)

Preferred

• Experience in a military, boarding school, or structured educational environment
• Familiarity with chain-of-command operations or uniformed services culture
• Experience supporting executive leadership and/or governing boards
• Event planning and coordination experience

Pay: $45,000.00 - $55,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Retirement plan
• Vision insurance

Work Location: In person