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Assistant Headmaster Jobs in Virginia (NOW HIRING)

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Assistant Headmaster information

See Virginia salary details

$12

$18

$26

How much do assistant headmaster jobs pay per hour?

As of Aug 29, 2026, the average hourly pay for assistant headmaster in Virginia is $18.87, according to ZipRecruiter salary data. Most workers in this role earn between $16.20 and $20.96 per hour, depending on experience, location, and employer.

What is an assistant headmaster?

An Assistant Headmaster supports the Headmaster in managing the daily operations of a school, ensuring that academic and disciplinary standards are maintained. Their duties often include supervising staff, assisting with curriculum development, handling student and parent concerns, and overseeing extracurricular activities. They also help implement school policies and may be involved in budgeting and staff evaluations. The Assistant Headmaster acts as a key leader within the school community, working to create a positive and effective learning environment.

How does an assistant headmaster balance administrative duties with student and staff support?

An Assistant Headmaster often splits time between handling administrative responsibilities—such as scheduling, policy enforcement, and compliance—and supporting students and faculty through mentorship, conflict resolution, and professional development. Balancing these duties requires strong organizational skills and the ability to prioritize urgent matters while maintaining approachability. Many Assistant Headmasters actively participate in school events and collaborate with teachers, counselors, and the principal to foster a positive school climate. This dual focus provides valuable experience for those interested in advancing to headmaster or district-level leadership positions.

What are the key skills and qualifications needed to thrive as an assistant headmaster?

To thrive as an Assistant Headmaster, you need strong leadership, educational management experience, and usually a relevant teaching qualification or advanced degree in education. Familiarity with school management software, student information systems, and compliance with educational standards is essential. Outstanding interpersonal communication, conflict resolution, and organizational skills set exceptional candidates apart. These skills ensure effective school operations, foster a positive learning environment, and support the overall mission and vision of the institution.

What is the difference between Assistant Headmaster vs Assistant Principal?

AspectAssistant HeadmasterAssistant Principal
CredentialsTypically requires teaching credentials and administrative experienceSimilar credentials, often with teaching certification and leadership experience
Work EnvironmentPrimarily in K-12 schools, especially private or independent schoolsCommonly in public and private schools, often in larger districts
Role FocusSupports the Headmaster in overall school management and policyFocuses on daily school operations, discipline, and student management

While both roles support school leadership, the Assistant Headmaster often has a broader strategic role, whereas the Assistant Principal handles daily operational tasks. The titles are used interchangeably in some regions, but generally, the Assistant Headmaster is more common in private schools, and the Assistant Principal in public schools.

What cities in Virginia are hiring for Assistant Headmaster jobs?

Cities in Virginia with the most Assistant Headmaster job openings:

Assistant Headmaster jobs near you

Principal Gifts Officer

Woodberry Forest, VA • On-site

Woodberry Forest School
Elementary and Secondary Schools • 201 - 500 employees
Learn more about Woodberry Forest Schoolexternal

$68K - $88K/yr

Full-time

Re-posted 14 days ago

Job description


Overview

Woodberry Forest School seeks an experienced and energetic advancement professional to identify, cultivate, and solicit major gifts supporting the school’s strategic imperatives. The Principal Gifts Officer is a senior member of the Alumni & Development Team and reports to the Assistant Headmaster for Institutional Advancement.


Woodberry Forest School is a leading independent boarding school for boys in grades nine through twelve, and one of the only all-boys, all-boarding schools in the United States. Nestled on 1,200 picturesque acres in Madison County, Virginia, and located near Charlottesville and Washington, DC. The school enrolls approximately 400 students and has been committed to shaping the lives of young men since 1889.


Key Responsibilities

  • Manage a fluid portfolio of approximately 175 prospects by qualifying new prospects, cultivating donor interest and building relationships that support the school’s mission.  

  • Plan and execute a total of 180 face-to-face visits per year. Complete contact reports and deliver timely and effective follow-ups to prospects and donors.

  • Work collaboratively to determine creative cultivation and solicitation strategies; and maintain active efforts to evaluate prospects identified through fieldwork, screening, and research.

  • Work collaboratively with the Director of Donor Relations to maintain a strong stewardship strategy for portfolio donors.

  • Maintain strong relationships with faculty, staff, and administrators to fully understand and articulate to prospects Woodberry today and its priorities for the future. 

  • Participate in major events on campus, i.e. Board meetings, Reunions, and other special events.  This will entail occasional weekend work.

  • Other duties as assigned.


Qualifications

  • Candidates must have a bachelor’s degree and direct front-line fundraising, sales, business development, or related experience.

  • Proven success in cultivating, soliciting, and closing major gifts.

  • Appreciation for, understanding of, and a strong commitment to the mission and value of Woodberry Forest School.

  • Superior interpersonal, written, and verbal communication skills.

  • Highly organized and able to manage and prioritize multiple and competing projects on an ongoing basis.

  • Self-starter with the ability to work independently as well as with a team.

  • Experience in developing and implementing strategies for achieving operating goals.

  • Ability to listen carefully and understand constituents’ needs while proactively responding to those needs in a consistent and timely manner.

  • Strong problem-solving skills combined with a collaborative approach.

  • Solid knowledge of Microsoft Office and Google Suite.

  • Able to exercise confidentiality and discretion.

  • Ability and willingness to travel extensively including overnight travel.

  • Periodic weekend and evening work is required.


Woodberry Forest School is an equal-opportunity employer.





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