Assistant Headmaster for Enrollment Management, Woodberry Forest School

Creative Independents; Danville (VA); Presencial; USD 150.000 - 210.000; Jornada completa

Descripción de la vacante

Woodberry Forest School seeks an innovative Assistant Headmaster for Enrollment Management to serve as a strategic partner to the Head of School and lead the Enrollment Division.

The role involves setting enrollment strategy, forecasting, and managing a multi-million dollar financial aid budget, while collaborating with trustees and other senior leaders to advance the school's mission and access goals.

Formación

• Bachelor’s degree required; Master’s degree preferred in education or related field.
• 5–10 years of enrollment, admission, and financial aid leadership experience.
• Strong analytical skills with multi-year enrollment modeling and forecasting.
• Familiarity with CRM platforms and executive dashboards.

Responsabilidades

• Formulate multi-year enrollment strategies aligned with school priorities.
• Forecast demographic trends and manage yield modeling across decision cycles.
• Set Net Tuition Revenue (NTR) goals and allocate financial aid strategically.
• Lead Enrollment Leadership Team and oversee division staffing and budget.
• Direct domestic and international recruitment and partner with external networks.
• Oversee summer programs, re-enrollment, and international study programs.

Conocimientos

Strategic enrollment

Forecasting

Budgeting

Data analysis

Educación

Bachelor’s degree

Master’s degree in education

Herramientas

Admissions CRM platforms

Data dashboards

Descripción del empleo

See the link for the complete position description:

Creative Independents: Assistant Headmaster for Enrollment Management, Woodberry Forest School

POSITION & STRATEGIC OPPORTUNITY

At an important moment in its evolution, Woodberry Forest School seeks an innovative, strategic, and collaborative enrollment leader to serve as Assistant Headmaster for Enrollment Management. Serving as a close strategic partner to the Head of School, a member of the Senior Leadership Team, and the leader of the Enrollment Division, the Assistant Headmaster holds the \"long view\" for the institution, answering the vital question: \"Where is the school going, and how do we build an enrollment strategy that gets us there?\"

ENROLLMENT DIVISION OPERATING PREMISE

The Enrollment Division exists to find and enroll the \"right boy\" for Woodberry. The right boy is one who wants to be at Woodberry and is open to being known, challenged, and loved—a young man willing to be seen as he actually is, pushed past his perceived limits, and shaped by a caring community. Where a boy comes from and what his family can pay tell us nothing about whether he belongs at Woodberry.

KEY RESPONSIBILITIES

1. Strategic Enrollment Management Formulate, articulate, and evaluate multi-year, data-informed enrollment strategies aligned with school-wide priorities. Conduct long-term enrollment forecasting, demographic analysis, and yield modeling across decision cycles. Serve as the primary guardian of the \"mission line\", protecting the \"right-boy standard\" when budget pressures, yield targets, or convenience conflict with institutional values.




2. Net Tuition Revenue (NTR) & Financial Aid Strategy Partner with the Head of School and Chief Financial/Business Officer to set annual Net Tuition Revenue (NTR) goals and tuition assistance budget strategies. Strategically deploy the $8.975M+ financial aid budget to maximize access for mission-appropriate applicants while avoiding \"barbell\" distribution, preserving financial sustainability, and managing discount rates. Oversee allocation policies to maintain Woodberry’s commitment to need-blind admission.




3. Division Supervision & Leadership Lead, coach, and develop the Enrollment Leadership Team, including the Director of Admission & Tuition Assistance, Director of Recruitment, and Associate Director of Enrollment. Oversee division staffing, organizational alignment, professional development, and budget administration. Cultivate a culture of accountability and high professional standards across all touchpoints.




4. Global Recruitment & Brand Positioning Direct high-level domestic and international recruitment strategies to expand Woodberry’s brand footprint in key and emerging markets. Cultivate strategic external partnerships with educational consultants, feeder schools, community-based organizations, and international referral networks. Partner closely with Marketing and Communications on brand positioning and digital campaigns.




5. Board & Leadership Relationships Serve as the senior enrollment advisor to the Headmaster and Board of Trustees, delivering regular, data-rich dashboards and funnel metrics. Partner with the Board’s Admission and Finance Committees on long‑term sustainability, financial aid strategy, and enrollment trends. Collaborate across campus with Academic Affairs, Athletics, and Student Life.




6. Auxiliary & Special Program Oversight Oversee summer program and camp management, including registration, payment structures, and marketing integration. Direct annual student re-enrollment processes and retention tracking. Manage contractual oversight for international study abroad programs.

CANDIDATE PROFILE & QUALIFICATIONS

Required Qualifications & Experience

• Education: Bachelor’s degree required; Master’s degree in education, business, executive leadership, or a related field strongly preferred.




• Leadership Experience: Minimum of 5–10 years of progressive enrollment, admission, and financial aid leadership experience, preferably within independent boarding schools or higher education.




• Financial & Analytical Acumen: Demonstrated expertise in multi-year enrollment modeling, financial aid leverage (discount rate management, packaging, NTR optimization), and data-driven forecasting.




• Systems Proficiency: Comfort and familiarity with admissions CRM platforms and analyzing data dashboards for executive leadership and trustees.

Personal & Leadership Characteristics

• Mission Alignment: Deep appreciation for all-boys, all-boarding residential education, single-gender developmental pedagogy, and Woodberry's Honor System.




• Executive Presence & Communication: Exceptional written, verbal, and presentation skills, with the ability to serve as an inspiring ambassador.




• Decisive & Empathetic Leadership: A balanced leadership style combining warmth, humility, and humor with the ability to make tough, mission-centered decisions.




• Collaborative Spirit: A commitment to a collaborative approach to enrollment management and to building an inclusive working environment that empowers direct reports while holding high standards of accountability.

ABOUT WOODBERRY FOREST SCHOOL

Woodberry Forest School is a premier, historic all-boys, 100% boarding school (grades 9–12), situated on a 1,200-acre campus in Central Virginia. Offering a transformative 24/7 educational and mentorship environment, the abiding concern of Woodberry Forest School is the personal growth of its students. The school provides a broad experience with balanced emphasis on academic, artistic, physical, and spiritual development, instilling self-confidence and a striving for continuing excellence throughout life.

School at a Glance

• Type & Location: All-boys, 100% boarding school (Grades 9–12) on a 1,200-acre historic campus in Central Virginia; 45 minutes from Charlottesville, 90 minutes from Washington, D.C., and Richmond.




• Student Body & Faculty: Approximately 400 boys from across the nation and around the world; 95% of faculty live on campus.




• Governance: Governed by a 126-year-old student‑run Honor System.




• Tuition & Financial Aid: Comprehensive tuition of $72,300. Need‑blind admission policy meeting 100% of demonstrated need. Over $8.9 million awarded annually; 46% of the student body receives financial aid, with an average grant of $50,140.

SCHOOL MISSION & COMMUNITY IDEALS

The purpose of the school is to develop in its students, under Christian principles, a high sense of honor and moral integrity, a deep respect for sound scholarship, a full acceptance of responsibility, a love of excellence, and a will toward personal sacrifice in service to others. It is likewise its mission, based on these ideals, to develop its students into leaders and to train them toward a useful contribution to the democratic society in which they live, and to give them thorough preparation for the best colleges and universities.

As a community, the school fosters an atmosphere of civility and cooperation. The underpinning of that effort is the honor system, which is not so much a rigid code as it is a way of life that is fundamental to the decency of the Woodberry community.

For more information about Woodberry Forest School, visit www.woodberry.org.