Faculty Guidebook 2025

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Faculty

What makes teaching and living at Woodberry Forest special?

Three things: our people, our place, and our culture.

Our student body is all-boarding, and more than 95 percent of faculty live on campus, creating an intimate, tight-knit community. We’re an allboys school, focused on developing young men who are lifelong learners with strong moral character.

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 intellectual thoroughness, moral integrity, good sportsmanship, and a reverence for things sacred. One of the school’s defining characteristics is our student-run honor system. Living and learning at Woodberry don’t just take place inside our classrooms. We seek faculty who are passionate about and trained in their discipline — but who are equally committed to connecting with boys on stage, on the athletic fields, and on dorm.

Classroom Life

At the heart of Woodberry’s academic culture is the idea that everyone on campus, from new students to the most experienced faculty, should be a lifelong learner. Woodberry teachers set high standards for their students, and our approach to academics is rooted in a belief that questions are more important than answers. We don’t tell boys what to think; we teach them how to think.

Courses in each department begin by helping students master the basics of a subject before moving on to a more critical, in-depth examination of each field. All classes meet four times per week: on Mondays for forty-five minutes, and then three times between Tuesday and Saturday for fifty-five minutes. Classes for all students are held on Saturday mornings to allow for shorter days on Tuesdays and Fridays, when most athletic contests are scheduled. 6:1

“What’s special about a boarding school is the level of relationship that you develop with the boys in so many venues, whether you’re working with them on the baseball field or you have them at the dining room table or you work with them on dorm. That allows the boys to feel more comfortable in your classroom. You’re learning to work with each other and let your guard down, and I think that allows the boys to be more vulnerable and open and not as intimidated in the classroom as they might be. These boys are very willing to try new things.”

Community Life

Coaching & Extracurriculars

Responsibilities for boarding school faculty don’t stop when the school day ends. Faculty serve as coaches, drama directors, or program advisors during two of our three trimesters. If you’ve never coached before, we’ll pair you with an experienced mentor who will help you develop new skills.

Duty

All faculty are on duty slightly less than once a week. During duty days you will spend time on dorm, particularly to ensure study hall is used well. This time on dorm is a great way to get to know students outside of the classroom, whether you’re stopping to chat before lights out, helping with homework, or watching TV with boys in the common room.

The Honor System

A pillar of Woodberry’s community is the honor system. Each spring the headmaster, after a student vote and faculty discussion, selects a group of seniors to serve as prefects. The prefects collectively administer the honor system. They take this responsibility extraordinarily seriously. Students promise not to lie, cheat, or steal. If found guilty of doing so, they can be dismissed from Woodberry by the headmaster at the recommendation of the prefects. The honor system creates an unusual and priceless sense of trust and respect between the students and faculty. As a teacher, you won’t need to worry about watching over their shoulders during exam periods or worrying that answers are passed around before homework is due.

Terry Dining Hall & Seated Meals

The Terry Dining Hall is the center of campus life for Woodberry boys, faculty members, and families. It serves three meals a day — all of which are open to faculty and their families — during the school year. Two of the dinners and one lunch each week are called “seated meals” and served family style. The rest are buffet. Stop by the dining hall and you’ll find families lingering together over a Tuesday night dinner or Sunday brunch. At lunch, faculty catch up on news or discuss the boys they’re teaching.

Community & Belonging

Woodberry’s commitment to community and belonging strives to center inclusiveness and affirmations of difference in every part of school life. Whether it is a Monday night chapel service or an all-school assembly, these moments provide an opportunity for every student and faculty member to come together under one roof. A sermon in chapel might focus on what it means to be a part of something bigger than yourself, while a sixth former at assembly might talk about the challenges he’s faced and offer advice to younger students. This is all tied to the core of the school’s mission, which seeks to shape our boys into young men who respect, embrace, and empathize with the differences of everyone in our community.

Advising

All Woodberry faculty serve as advisors to a small group of students and serve as the first point of contact for parents and students when a boy is facing a personal or academic challenge. Advisors eat a family-style, coat-and-tie dinner with these students once a week before chapel. You’ll get to know these students very well and will find these relationships to be some of the most important you form at Woodberry.

WFSPN

WFSPN, Woodberry’s student-run production network, allows students to pursue their interests in sports broadcasting and journalism. Broadcasts give parents an opportunity to watch their boys compete or perform from miles away and allow alumni and friends to be a part of our community, even when they aren’t on campus.

“My job as an advisor is to partner with parents to help my advisees in any way I can. Whether it’s an academic concern, trouble on dorm, or a challenge at home, my hope is that boys and parents see me as the first advocate and source of support on campus.

I know that my advisees will develop strong relationships with multiple adults on campus, but I also expect that their relationship with me will be one of the most important and formative they’ll develop in their time here.

Probably the greatest joy of advising at Woodberry is getting a front-row seat to a boy’s growth throughout this exciting, wonderful (and occasionally turbulent) time of their lives. Boys don’t always mature as fast as we’d like! But helping them take advantage of opportunities, grow through setbacks, and take steps toward adulthood has been one of the most fulfilling aspects of my work here.”

EXPEDITION WEEK

We believe that boys are hardwired to connect — to each other, to adult role models, and to lives of purpose and integrity. During Expedition Week, Woodberry focuses on these connections, creating time and space for the whole school to break out of our routine. The expeditions are unique to each form, but bound together by a common experience of brotherhood and engagement with faculty.

What is it like to live here?

Whether you live on dorm or elsewhere on campus, working at Woodberry is a demanding job. Between teaching, coaching, and regular dorm duty, long days are the norm. But this is also a place where you’ll develop deep friendships with colleagues and students. Housing and meals for you and your family are part of your compensation.

Woodberry Forest School

Charlottesville

Richmond

The campus is truly idyllic. Faculty and their families enjoy access to a pool, two gymnasiums, squash and tennis courts, and a nine-hole golf course. Faculty children roam free with their friends, wandering from the athletic fields to the river and back to the dining hall without their parents worrying about their safety. If you have children, they’re sure to find close friends among the other forty-five school-age children on campus.

Washington, DC

Woodberry is in a rural location. The town of Orange, about ten minutes away, has a pharmacy, grocery store, and a few restaurants. Culpeper, a larger town, is twenty minutes away and has a small hospital and more extensive shopping and dining options. Charlottesville, home to the University of Virginia, is forty-five minutes from campus. Washington, DC, is between ninety minutes and two hours away, depending on traffic and where in the DC area you’re headed.

“We moved to Woodberry in the midst of the pandemic in 2020. We had been living in Minneapolis, where I was teaching at the University of Minnesota and my husband, Trevor, was an English teacher at the Breck School. Trevor graduated from Woodberry in 2004, and for many years I was adamant that I didn’t want to live here. I had misgivings about being at a place that was so clearly “his school,” and I was uncertain about what an all-boarding environment would be like. But as the years went on and we were just starting to grow our family, my opinion changed and the thought of raising our kids on a boarding school campus seemed wonderful. So we took the plunge and arrived in Virginia during peak Covid. The community could not have been more welcoming, and people went out of their way to say hello. We felt very lucky to be here during such a stressful time.

After our first year at Woodberry, I started teaching English on a part-time basis. Because we were living off-dorm, being in the classroom gave me an opportunity to really get to know a group of boys. It’s been fun to see them in the dining hall, at their sporting events, or just around campus. There is such a big difference between teaching college students and teenagers in high school. At Woodberry, I feel like we are focused on the long game and building relationships with the boys, which is something I didn’t experience at the university level.

Beyond the classroom, one of my favorite aspects is the campus itself. It’s hard to imagine a more beautiful place to live. We look out over the Blue Ridge Mountains, with the Rapidan River and all the trails to explore, but we also have Charlottesville and Washington, DC, not very far away, so we get the best of rural life with access to some really fun, urban opportunities.

I am grateful to live in a community where I can know everyone’s name and where people support each other in many different ways, big and small. For our kids, it’s such an incredible place for them to grow up. There are lots of faculty kids on campus, and you’ll see them out playing together. I’m confident that if I ever need anything, people will be there to help, which feels really special. We are very happy here, and we plan on staying for a long time.”

How will Woodberry support you?

Woodberry seeks lifelong learners. Faculty can apply for financial support from the school if they wish to pursue graduate degrees or professional development. Woodberry also pairs new teachers with experienced mentors, with additional support provided by the department chair and the assistant headmaster for academic affairs.

The Walter William Craigie Teaching Endowment

Established in 1983 by Helen and Walter W. Craigie, Sr. ’22, and supported by their son, the late trustee Walter W. Craigie, Jr. ’48, this program supports the pursuit of graduate degrees by members of the faculty. Current and recent Craigie Scholars include:

 Chad Bullock, History: MA in history at Gettysburg College

 SaraGrace Kimball, Math: MEd in curriculum and instruction at the University of Virginia

 Chase Spong, Admission: MEd in independent school leadership at Vanderbilt University

 Taylor Tucker, Computer

Science: MS in data science at the University of Virginia

What New Faculty Think You Should Know

“I discovered early on that working at Woodberry demands an all-hands-ondeck mentality. It wasn’t until the wildly challenging third-form expedition in the fall of my first year that I truly grasped this culture of faculty and staff going above and beyond expectations to ensure the best possible experience for our boys.”

“One of the reasons I wholeheartedly wanted to accept this job is because I felt very supported even from the beginning. What I love even more is that the support hasn’t stopped since being hired. The faculty, both in and not in your department, are always willing to help you, and the Woodberry community shows a lot of care and love for each other.”

“Seek balance. Professional responsibilities of a boarding school can often overtake personal lives. Honor your work-related commitments, but be sure to make time for personal plans as well.”

“Teaching at Woodberry is an experience of intellectual freedom. I’m consistently impressed with the trust each department bestows upon its faculty members. If you’re passionate about a certain topic related to your field, Woodberry is willing to let you pursue your interests.”

Kenan-Lewis Fellowship

The Kenan-Lewis Fellowship Program at Woodberry Forest School gives recent college graduates a short-term, two- to three-year appointment to the school’s faculty. The program provides a guided, hands-on apprenticeship designed to create a solid foundation in independent school teaching. In addition to classroom experience, fellows have the opportunity to pursue a master’s degree related to their academic discipline or a master’s degree in teaching and learning from the University of Virginia. By the end of the fellowship, they are qualified to seek full-time teaching positions at top schools anywhere in the country.

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DIFFERENT DEGREE PROGRAMS BEING PURSUED BY OUR 4 CURRENT FELLOWS

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CURRENT FULL-TIME FACULTY MEMBERS WHO STARTED AS KENAN-LEWIS FELLOWS

Mentorship

Fellows are assigned to an academic department, where they work with experienced mentors, observe master teachers, and learn to design lessons and teach classes. As they spend time at Woodberry, fellows gain more responsibility and independence in their work. Outside the classroom, they serve as assistants in extracurricular programs ranging from athletics to the arts, where again they work with mentors to gain practical experience, from running practices to coaching a game or directing a scene. Living on campus, they work alongside the full-time faculty in the school’s residential life program and experience fully the life of the community.

Most important, fellows cultivate the art of building substantial, enduring relationships with their students and guiding them as they navigate the challenges of boarding school and adolescence. During the length of their fellowship, they have what amounts to a supported and mentored full-time faculty position. The guidance Woodberry’s fellows receive at this early stage in their careers pays off: Since the launch of the Kenan-Lewis Fellowship in 2007–2008, more than two-thirds of the fellows are still teaching at an independent school.

How to Apply

We accept applications for the Kenan-Lewis Fellowship from college seniors and very recent graduates for the upcoming academic year until January 15. In order to be considered for the fellowship, candidates must have a college major in an academic subject taught at Woodberry: English, history, Spanish, Latin, biology, chemistry, physics, mathematics, and computer science. 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) College transcript

(4) Two letters of recommendation

All application materials should be submitted to kenan_lewis@ woodberry.org. Questions should be directed to the director of the fellowship, Matt Boesen (matt_boesen@woodberry.org). To learn more, visit woodberry.org/KLF.

“I decided to become a Kenan-Lewis Fellow simply because it was too good of an opportunity to pass up. I was nervous to start, but I’ve realized that being a fellow invites support from all aspects of the school. When it comes to teaching, I’ve got a great faculty mentor who sits in on my classes and gives me tips and we get to discuss teaching philosophy. And then there’s also the coaching side of it, which is really fun. I’ve been coaching varsity and JV football, and it’s a great opportunity to take a chunk of your afternoon and go have fun with the student-athletes. The experience as a whole has been a great balance between academics and athletics. All of it has been incredibly fulfilling. Spending your time with these boys and the energy they bring, as well as the intellect and the curiosity, is really invigorating.”

Contact Information

Matthew C. Boesen

Matt Boesen is chair of the history department, director of faculty recruitment, and faculty advisor to the headmaster. He served as Woodberry’s dean of faculty for eight years from 2015 to 2023. Matt designed and currently teaches two upperclass honors courses: The Constitution and Democracy and Dictatorship between the World Wars, as well as Woodberry’s third-form history course, Stories and Histories. Matt earned an AB from Yale University and an MA and PhD from the University of Virginia.

E matt_boesen@woodberry.org

Abigail C. Mills

Abbie Mills is the assistant headmaster for academic affairs and teaches ECLIPSE, a problem-solving class for third formers. She came to Woodberry in 2016 to teach engineering following a career at NASA’s Johnson Space Center where she was a senior project engineer and project manager specializing in fuel cell systems. Abbie holds a degree in mechanical engineering from Rice University.

Byron C. Hulsey

Byron Hulsey became the school’s ninth headmaster in 2014. He also teaches in the history department. He graduated from Woodberry in 1986 and was senior prefect. He was a Jefferson Scholar at the University of Virginia, where he 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 returning to Woodberry.

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