Assistant Head of School Jobs

The Executive Assistant to the Head of School is a confidential partner to the Head and the day-to-day liaison to the Board of Trustees. The role keeps the Head's office running smoothly, manages the cycle of board work, leads events hosted by the Head of School and other key all-school events, and assists in advancing all-school initiatives. The Executive Assistant is often the first point of contact between the Head and trustees, faculty, staff, parents, alumnae, and students, and represents the mission and values of RPCS in every interaction.

Head of School

• Manages and prioritizes the Head of School's daily schedule, resolving conflicts and aligning the Head's time with institutional priorities.
• Serves as the Head's primary point of contact by handling mail, screening calls and email, answering inquiries when appropriate, and routes items to the appropriate administrator.
• Assists with the functioning of the Senior Leadership Team by scheduling meetings, taking notes, and other administrative and operational tasks needed for the team to function effectively.
• Prepares briefing materials before meetings and appointments, and maintains a system for tracking follow-up items, commitments, and deadlines for the Head's office.
• Oversees the Head's visiting calendar and coordinates campus tours, food service, and other details.
• Works with the Advancement Office to coordinate donor and other donor-centric visits with the Head of School.
• Schedules the Head's business travel and manages the Head's expense reports and office budget.
• Coordinates with the Advancement and Human Resources departments to provide the Head with appropriate materials for correspondence around birthdays, condolences, and other major life events, and ensures that such communications are timely.
• Compiles data and conducts preliminary research as needed for the Head when appropriate.
• Works on other projects, reports, and assignments to assist the Head or as delegated by the Head.

Trustees

Assists and supports the Head of School with trustee matters, including:

• Scheduling and facilitating board and committee meetings, including drafting agendas with the Head and Board Chair, and assembling and distributing board packets and other board information and mailings.
• Attending designated board meetings to take minutes, assisting the Head with follow-up, and maintaining official board minutes, resolutions, and corporate records.
• Facilitating the organization of and materials for new trustee orientation program and the annual trustee retreat.
• Maintaining, updating, and distributing the trustee directory and Trustee Orientation Handbook each year.
• Serving as the day-to-day contact for trustees and handling of board logistics, set-up, food, travel, and purchasing, etc.

All-School support

• Communicates with faculty and staff by email on behalf of the Head of School.
• Schedules standing appointments and meetings between employees and the Head.
• Prepares beginning-of-year materials for new and returning faculty and staff, and helps organize new employee orientation.
• Serves as a key member of the Calendar Committee to build the All-School Calendar and resolve operational issues; assists with calendar and room reservations, checking for conflicts.
• Coordinates with the leads for all-school teams and committees on status updates for larger initiatives.
• Assists with major projects such as planning, implementing, and scheduling for major initiatives such as accreditation and strategic planning, and tracks progress on initiatives designated by the Head.
• Attends and facilitates events for the Head of School, including some evenings and during accreditation visits.
• Assists the Human Resources team with tasks as appropriate.
• Supports the Director of Academics and Curriculum and the Chief Institutional Advancement Officer with employee hires that run through their offices.
• Manages the school's association memberships (NAIS, AIMS, and others).

Events

• Coordinates all events hosted by the Head of School and designated all-school events.
  • Duties for Head of School events include, but are not limited to:
    • Arranging all event details including work orders, menu planning, ensuring appropriate staffing, ordering flowers and other items.
    • Attending events to ensure they run smoothly.
    • Sending appropriate invites and facilitating thank you notes in a timely manner.
    • Collaborating closely with our facilities and dining services using established request protocols.
    • Ensuring the processing of invoices.
  • Duties for Commencement include, but are not limited to:
    • Collaborating with Upper School office in planning and execution o
    • Coordinating with the Head of School and Upper School Head on Commencement, Orders diplomas, invitations, faculty robes, stage, chairs, flowers, and greens.
    • Arranging the reception following Commencement.
    • Supervising the smooth execution of Commencement Day, and serves as liaison for trustees attending.
  • Duties for Convocations include, but are not limited to, scheduling event room usage and any other necessary set-ups.
• Arranges set-up and food for faculty/staff breakfasts, faculty professional days, and other events involving the Head.
• Coordinates event details for Opening Week and end-of-year employee work days.
• Supports other offices with high-impact events, including those led by Admissions and Advancement.

Additional projects and tasks

• Oversees the common spaces on the first floor of the Ward House, and makes any necessary requests for housekeeping, etc.
• Completes Event Set-up, Purchase Order, and Check Request forms.
• Prepares the Head's summer mailings to new and departing students and the Cum Laude mailing.
• Orders supplies for the Main Office and Head's Office and orders badges for new employees.
• Other duties as assigned.

Working conditions:

• The Executive Assistant to the Head of School position is a full-time, exempt 12 month position.

• The individual in this position is expected to work during all hours as may be assigned by the School and during other hours for events and activities including regular evening and weekend hours for meetings and events.
• The Executive Assistant to the Head of School is expected to perform their job duties on campus, unless otherwise permitted by the Head of School.

COMPENSATION DISCLOSURE: In accordance with Maryland's Equal Pay for Equal Work Act, we are committed to providing transparent wage information for all posted job opportunities. The salary range for this position is $70,000-$85,000 annually. Compensation is determined based on factors such as Experience, Qualifications, and Internal equity.

BENEFITS AND ADDITIONAL COMPENSATION: Additionally, this position includes a comprehensive benefits package and other forms of compensation, including:

• Employer-provided health benefits: medical insurance, dental and vision insurance, disability insurance, life insurance, mental health support services, wellness program, free access to fitness center onsite, and free lunch daily.
• Paid time off for full time and full time reduced employees: vacation days, sick leave, personal days, winter break & spring break based on school calendar schedule.
• Retirement plan: 403(b) retirement plan with employer match contribution (required minimum hours worked after 1 year of service.)

EOE STATEMENT: RPCS is an Equal Opportunity Employer. We provide equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, veteran status, or any other legally protected characteristic. We are committed to ensuring a diverse and inclusive workplace, and all employment decisions are based on merit, qualifications, and organizational needs. If you require accommodations during the application process, please contact Human Resources.

To Apply:

For best consideration, please attach your resume and cover letter by November 23, 2026.

Qualifications

Education

Bachelor's degree preferred; equivalent work experience considered.

Experience

Minimum of 3 years of executive or administrative support experience, ideally supporting a senior leader, head of school, or board. Experience in an independent school or nonprofit preferred.

Skills and abilities

• Dependable professional with excellent organizational skills, enthusiasm, and a positive attitude.
• Absolute discretion with confidential and sensitive information, including personnel and board matters.
• Strong oral and written communication skills, including minute-taking and drafting on the Head's behalf.
• Strong computer skills: Microsoft Word and Excel, Google Workspace, and Zoom; familiarity with Blackbaud or Veracross is a plus.
• Sound judgment; able to act independently and to know when to escalate concerns to appropriate individuals or offices.
• Ability to manage many projects and deadlines at once in a busy, open, and active environment.
• Takes initiative and is able to work independently to move projects forward.
• Eagerness to learn, adaptability, and commitment to one's own professional growth.
• Ability to work collaboratively with colleagues and all members of the RPCS community.
• A warm, welcoming presence who stays calm under pressure.