Career Opportunities

Careers Opportunities at Woodberry

List of 6 items.

  • Assistant Headmaster for Enrollment Management

    The assistant headmaster for enrollment management is responsible for all matters pertaining to the school’s enrollment management program, including strategic oversight of the admission, tuition assistance, and retention efforts.  Leading a nine member admission team, the assistant headmaster for enrollment management will work closely with the director of admission & tuition assistance and the associate director of admission operations to refine and implement the school’s strategic enrollment management plan.  Reporting to the headmaster and serving on the school’s executive leadership team, the assistant headmaster for enrollment management will provide critical insights and perspective on the strategic direction of the school community. The assistant headmaster for enrollment management will work closely with the director of strategic communications to define and market the school’s value proposition.  Additionally, the assistant headmaster for enrollment management will partner with the dean of students to formalize and implement retention initiatives and efforts.

    Profile characteristics of the most compelling candidates include:
    • Bachelor’s degree required, Master’s degree preferred
    • Substantive admission and financial aid experience/leadership in an independent school and/or college
    • Demonstrated proficiency with research and data analytics
    • Strong background in communication strategies (print, web, social media)
    • Superior communication and public relation skills
    • Significant experience leading a team
    • Understanding of recruitment trends.  Experience recruiting domestically and overseas.
    • Proven record of building relationships with various constituents and stakeholders (school placement officers, educational consultants, alumni, past/current parents)
    The assistant headmaster for enrollment management must be willing to travel seasonally both within the United States and internationally.  The assistant headmaster for enrollment management is expected to represent Woodberry more broadly as a school ambassador while traveling. Most of all, the assistant headmaster for enrollment management at Woodberry Forest must believe deeply in the mission and purpose of the school and be able to communicate that passion effectively. The assistant headmaster for enrollment management will live on campus and be expected to participate fully in the life of the school.

    Woodberry Forest School is one of the nation’s premier independent boarding schools for boys.  Located on 1,200 beautiful acres in Madison County, Virginia, near Charlottesville and Washington, DC, Woodberry is an all-residential school.  Woodberry enrolls approximately 400 students from the United States and abroad.   Since its founding in 1889, Woodberry Forest has become recognized internationally as a leader in the education of boys.  Students are carefully selected from an outstanding group of strong applicants.

    Woodberry maintains a generous financial aid program with forty-five percent of students receiving aid, an investment each year of over $6.5 million. The school is committed to enrolling the best possible students regardless of a family’s ability to pay and is in the midst of a substantive and longstanding effort to build the endowment for tuition assistance in the current campaign. The faculty includes men and women of significant educational background and experience. All students and most faculty and their families live on campus. 

    Woodberry Forest School is an equal opportunity employer.
    Interested applicants should send a cover letter, résumé and references by February 15, 2020, to or by mail to Debbie Lloyd, director of personnel, at Woodberry Forest School, 10 Woodberry Station, Woodberry Forest, Virginia 22989.
  • Assistant Director of the Amici Fund

    The Assistant Director of the Amici Fund is a two year fellowship within the External Affairs Office at Woodberry Forest School. You will be part of a highly productive team primarily responsible for helping ensure the success of the Amici Fund (Woodberry’s annual fund), which consistently garners a nationally leading 60%+ participation rate among alumni donors. In addition, you will work extensively with members of the Alumni Relations, Donor Relations, and Communications teams in crafting strategies and messaging to reach, inspire, and steward Woodberry alumni to support the school. Over 400 loyal Woodberry alumni serve as class volunteers, and your assistance in organizing and coordinating their efforts will help to drive the success of the Amici Fund.
    Living in a faculty apartment within a Woodberry dormitory, you will have the opportunity and responsibility to serve as a member of the rotating duty team for that dorm, and as a mentor to Woodberry students -- boys in the 9th-12th grades hailing from 23 states and 25 countries.  
    The Assistant Director reports to the Director of the Amici Fund & Alumni Relations and is a member of the advancement team.

    Specific Responsibilities:

    • Assist in developing marketing plans for alumni in an effort to educate alumni about the Annual Fund and secure gifts.
    • Collaborate with the Director of the Amici Fund to set annual giving goals for all constituent groups and assist in developing strategic plans for achieving these goals.
    • Work closely with donor relations to formulate and execute a communications and stewardship program.
    • Conduct prospect research, development, relationship-building, cultivation, and solicitation.
    • Plan and coordinate off-campus alumni gatherings targeted to alumni.
    • Work with the Director of the Amici Fund using Google’s G Suite and Microsoft Office products to conduct analysis of giving trends and alumni demographics in order to improve annual fund performance
    • Solicit reunion attendance and promote reunion-year giving.    
    • Work closely with the young alumni members of each regional association to promote participation and increase membership.
    • Maintain and promote the use of Woodberry Connect and develop a communications strategy for reaching young alumni.
    • Network and communicate with peer-school annual giving professionals to compare best practices.  In addition, pursue professional development opportunities on an annual basis.
    • Attend on-campus events to foster positive relationships with relevant constituents.
    • Work with graduating senior class to familiarize them with Woodberry’s alumni office resources and the school’s culture of giving.
    • Take on other special projects and responsibilities as assigned.
    Bachelor’s degree required.

    • Demonstrated success in motivating and directing volunteers.
    • Knowledge of the independent school and/or university environment preferred.
    Skills and Abilities:

    • Understanding of and strong commitment to the mission of Woodberry Forest School.
    • Superior interpersonal, written, and verbal communications skills.
    • Highly organized and able to manage multiple and competing projects on an ongoing basis.
    • Flexible with the ability to work independently.
    • Ability to work cooperatively to achieve common goals.
    • Ability to provide direction and motivation to others through communication, modeling appropriate behavior, optimism, and high achievement.
    • Openness to new ideas and their implementation.
    • Ability to react and adapt to changing environments appropriately.
    • Ability to listen carefully and understand constituents’ needs while proactively responding to those needs in a consistent and timely manner.
    • Demonstrated analytical and fund-raising skills with the ability to recognize opportunities, identify high-capacity activities, and prioritize to attain goals.

    • High professional and ethical standards for handling confidential information.
    • Weekend work required.
    • Travel required.
    To apply for this position, please send your cover letter, résumé, and the names of three references to Ed Stone at
  • Staff and Administrative Faculty Positions

    Thank you for your interest in applying to Woodberry Forest School. Please click on the following link for all available openings at this time. 

    Woodberry Jobs Board
  • Learn More About Faculty Careers at Woodberry

    What makes teaching and living at Woodberry Forest School special? Three things: Our people, our culture, and our place. Our student body is all-boarding, and more than 90 percent of faculty live on campus, creating an intimate, tight-knit community. We’re an all-boys school, focused on developing young men who are lifelong learners with a strong moral character. One of the school’s defining characteristics is a nearly 120-year-old honor system that is entirely student run. 
    Our campus is set on 1,200 acres in the foothills of the Blue Ridge Mountains. This is a place where we can focus on teaching and learning without distractions. Students, faculty, and faculty families take full advantage of our safe and beautiful campus, enjoying hiking and biking trails in the woods or the natural beauty of the Rapidan River, which borders our land. 
    Our culture is based on moral integrity, intellectual thoroughness, a reverence for things sacred, and good sportsmanship. We seek faculty who are passionate about and trained in their discipline  but who are equally committed to working with boys on stage, on the athletic fields, and on dorm. Living and learning at Woodberry doesn’t just take place inside our classrooms. View the faculty guidebook
    Biography/contact info
    Matthew C. Boesen is Woodberry’s dean of faculty. Before beginning that role in 2015, he was a member of the history department for fourteen years. He previously taught for three years at Phillips Exeter Academy. Matt earned an AB from Yale University and a MA and PhD from the University of Virginia. Please direct any questions about professional opportunities to Matt.
    Phone: 540-672-6021
    Byron C. Hulsey became the school’s ninth headmaster in 2014. He graduated from Woodberry in 1986 and was senior prefect. He was a Jefferson Scholar at the University of Virginia and studied history. He taught for two years at Bryanston School, a boarding school in Blandford, England, before returning to his native Texas to earn MA and PhD degrees from the University of Texas at Austin as a Patterson-Banister Fellow in American History. Byron served on the Woodberry faculty from 1998 to 2000 as assistant director of college counseling and in the history department. He was assistant headmaster at Norfolk Academy and was head of school at Randolph School in Huntsville, Alabama for eight years before coming to Woodberry. 
  • Kenan-Lewis Fellowship Program

    The Kenan-Lewis Fellowship Program at Woodberry Forest School gives recent college graduates a two-year appointment to the school’s faculty. Established by the William R. Kenan Jr. Charitable Trust in honor of alumni Frank Hawkins Kenan ’31 and Lawrence Lewis, Jr. ’37, the program provides a guided, hands-on teaching and coaching apprenticeship designed to create a solid foundation in the profession. As the two years unfold, fellows gain independence, and by the end, they are qualified to seek full-time positions at top independent schools and will have attained a masters degree in education from the Curry School at the University of Virginia. 

    Fellows are assigned to an academic department, where they work with experienced mentors, observe master teachers, and learn to design lessons and teach classes. Outside the classroom, they serve as assistant coaches in one of our extra-curricular programs such as athletics or the arts, where again they work with mentors to gain practical experience, from running practices and teaching skills to coaching a game or directing a scene. 

    Living on campus — supervising dormitories and extra-curricular activities — they experience fully the work of the school and the life of the community, and they learn the art of guiding students in daily life and building substantial relationships. 

    Each fellowship carries a salary of $26,000 plus living quarters, meals in the school dining room, and health care benefits.

    We accept applications from college seniors and very recent graduates for the upcoming academic year until January 15.

    Candidates chosen to interview will be notified by February 15. Applicants should submit the following: (1) a cover letter; (2) a résumé indicating previous education, employment, athletic and extracurricular experience, and special interests and skills; (3) their college transcript; and (4) two letters of recommendation.

    If you have filed an application with one of the major faculty placement agencies, such as Carney Sandoe & Associates, Southern Teachers Agency, or Educator's Ally, the only submission required is a letter of application and an email to Matt Boesen to ensure your information on file has been downloaded from the agency for consideration. 

    To discuss this opportunity further please contact, Matt Boesen, director of the Kenan-Lewis Fellowship Program. 

    Phone: 540-672-6021 

    Please submit all application matierials to
  • Meet Two Recent Kenan-Lewis Fellows

    Meet Kristyn Wilson
    2016-18 Teaching Fellow, now a full-time member of the English faculty

    Huntsville, AL
    Randolph School, BA in English and Global Studies from UNC-Chapel Hill
    Teaching and coaching assignments:
    English 300, English 500 JV Cross Country, varsity swimming

    Observations about teaching boys in a boarding school setting:
    The rate at which boys cultivate relationships with both peers and teachers is exciting and astonishing. After only a few weeks, my students have crossed the threshold of familiarity and are willing to be vulnerable and take academic and personal risks in class, on the field, and on dorm, knowing already that their classmates will encourage them. Given the high level of access we as teachers have to the boys throughout the day, I am able to more fully support and challenge my students in these risks, which is an awesome opportunity for
    all of us.

    Meet Ty Adams
    2016-18 Teaching Fellow, now a full-time member of the history faculty

    West Hartford, CT
    Kingswood Oxford School, BS History from Appalachian State University
    Teaching and coaching assignments:
    US History, Stories & Histories: An Introduction to Historical Analysis
    varsity soccer, varsity baseball
    Memorable Woodberry moment:
    My first seated meal and chapel night was pretty noteworthy. Watching the old and new boys interact with one another and their teachers made it clear this place was special. There was a palpable feeling in the air; everyone was finally home again. Following dinner, watching the procession of 400 boys fill in the beautiful St. Andrew's Chapel was a humbling experience. 
    On teaching boys in a boarding school setting:
    I have seen the impact a residential community has on these boys from the start. The boarding school environment makes teachers so accessible to the boys and allows us to know each student and their needs.  We can effectively impact their lives in the classroom and as a whole. Whether it’s in class, on the playing fields, or just on dorm, the boys are extremely willing to learn how to be the best versions of themselves. 
Woodberry Forest admits students of any race, color, sexual orientation, disability, religious belief, and national or ethnic origin to all of the rights, privileges, programs, and activities generally accorded or made available to students at the school. It does not discriminate on the basis of race, color, sexual orientation, disability, religious belief, or national or ethnic origin in the administration of its educational policies, admissions policies, scholarship and loan programs, and athletic or other school-administered programs. The school is authorized under federal law to enroll nonimmigrant students.