Career Opportunities

Careers Opportunities at Woodberry

List of 5 items.

  • 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
  • Executive Assistant to the Headmaster

    The Executive Assistant to the Headmaster reports directly to the headmaster, serves as the liaison between all members of the school’s community and the headmaster, and works closely with the school’s senior administrators. The Executive Assistant to the Headmaster is an essential, strategic, and loyal confidante for the headmaster and a partner in his responsibility to oversee, interact with, and ensure the highest levels of quality for the school’s programs and initiatives. The Executive Assistant to the Headmaster is charged with using keen judgment to make decisions to facilitate the headmaster’s executive responsibilities.

    In this capacity, the Executive Assistant to the Headmaster takes responsibility for:
    ●     Assisting in the management of the headmaster’s daily and weekly schedule and coordinating travel arrangements with a keen eye to anticipating conflicts and inefficiencies

    ●     Preparing and editing correspondence, communications, and PowerPoint presentations for the headmaster’s use

    ●     Maintaining and accessing electronic and hard copy filing systems

    ●     Arranging and coordinating meetings and events

    ●     Engaging with faculty, staff, students, parents, prospective parents, and guests in ways that promote the positive and relational culture of the school

    ●     Providing confidential, consistent and professional support to the headmaster, and also support the dean of faculty, dean of students, and board secretary as requested

    ●     Fulfilling all other associated duties requested by the headmaster
    Essential Competencies/Qualities

         Organizational and planning skills and capacities, with the instinct to anticipate upcoming conflicts, challenges, and opportunities

         Communication skills

         Analyzing and solving problems

         Discretion, judgment, and decision-making

         Initiative and proactive instincts


         Attention to detail and accuracy

         Flexibility and adaptability

         Ability to work independently or with minimal supervision

         Sense of humor

    ●     Bachelor’s Degree required; graduate study/degree preferred
  • 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.