Assistant Headmaster for Enrollment and Residential Life

Job Description

Position Summary:
The Assistant Headmaster for Enrollment and Residential Life provides strategic leadership for all aspects of the school's enrollment and residential life programs, including recruitment, admissions, retention, financial aid strategy, and enrollment marketing. This role is responsible for developing and implementing a comprehensive enrollment strategy that supports the school's mission, community, and long-term financial sustainability.
Strategic enrollment management in independent schools extends across the entire student lifecycle. Successful implementation requires alignment of market research and strategy, educational program and school brand, recruitment and selection of new students, tuition and financial aid strategy, school culture and community, retention of current students, and student educational outcomes. The Assistant Headmaster ensures that these interconnected elements are thoughtfully coordinated to create a cohesive and sustainable enrollment strategy.
Working closely with the Headmaster and senior leadership team, the Assistant Headmaster leads the admissions team and partners across departments to attract, enroll, and retain a diverse, mission-aligned student body. The role combines relationship-driven admissions leadership with modern data-informed strategy, ensuring that enrollment practices are responsive to changing demographics, market conditions, and family expectations.
A deep understanding of independent boarding school culture and operations is essential, including expertise in residential life leadership, student support structures, and the full student experience beyond the classroom. The Assistant Headmaster must possess strong knowledge of the boarding school market and the factors that influence family decision-making domestically and internationally. The Assistant Headmaster must be able to authentically communicate how the school delivers on its mission and ensure that the expectations set during the admissions process align with the lived experience of students and families.
Key Responsibilities:
Enrollment Leadership
•Develop and implement a comprehensive multi-year strategic enrollment plan aligned with the school's mission and institutional priorities.
•Ensure that strategic enrollment planning integrates market research, educational program positioning, school brand, recruitment strategy, financial aid strategy, student retention, and student outcomes.
•Establish and monitor annual enrollment targets, yield goals, and retention benchmarks.
•Analyze enrollment data, demographic trends, and market conditions to inform recruitment, selection, and retention strategies.
•Lead ongoing research and assessment of the independent school and boarding school marketplace to identify emerging opportunities and competitive positioning.
•Provide regular reports, projections, and insights to the Headmaster and senior leadership team.
•Serve as a key member of the school's administrative team contributing to institutional planning and strategic initiatives.
•Ensure enrollment messaging and practices accurately reflect the school's academic and boarding programs so that the promises made during recruitment align with the actual student and family experience.
Admissions & Recruitment
•Oversee the full admissions process from inquiry through enrollment and onboarding.
•Lead recruitment initiatives including open houses, regional, international, and on-campus admissions events, school visits, interviews, and outreach to feeder schools and community partners.
•Develop recruitment strategies informed by market research and aligned with the school's mission, program strengths, and long-term enrollment goals.
•Manage international student recruitment and admissions, including compliance with student visa requirements, travel to international recruitment events, and coordination with families abroad.
•Cultivate relationships with educational consultants, agents, and community organizations.
•Ensure a welcoming, personalized, and mission-aligned experience for prospective families.
•Evaluate and refine admissions policies, procedures, and timelines to support thoughtful selection of students who will thrive academically, socially, and within the residential community.
Enrollment Strategy & Retention
•Develop and implement strategies to strengthen student retention and family satisfaction, recognizing retention as a critical component of enrollment stability and long-term school health.
•Work collaboratively with residential life leadership to ensure the boarding program supports student engagement, belonging, and long-term retention.
•Partner closely with academic leadership, residential life, advising programs, and student support services to ensure students are successfully integrated into both the academic and residential community.
•Lead cross-departmental collaboration to ensure the school delivers on the expectations and commitments communicated to families during the admissions process.
•Identify and address factors that influence student engagement, persistence, and re-enrollment.
•Evaluate the student experience from enrollment through graduation to ensure alignment between institutional promises and educational outcomes,
•Monitor and analyze the enrollment funnel, including inquiry, application, acceptance, and yield rates.
•Identify opportunities to expand recruitment markets locally, nationally, and internationally.
Financial Aid & Tuition Strategy
•Collaborate with the Headmaster and finance leadership to align tuition and financial aid strategy with enrollment goals and net tuition revenue targets.
•Oversee tuition assistance policies and processes.
•Use financial aid strategically to support accessibility, mission alignment, and enrollment objectives.
•Evaluate financial aid allocation and tuition strategy in relation to market positioning, family affordability, and long-term sustainability.
Marketing & Enrollment Communications
•Partner with the communications and marketing team to develop enrollment marketing strategies and messaging.
•Ensure consistent and compelling storytelling across admissions materials, digital platforms, and events.
•Ensure marketing and admissions messaging reflects an authentic portrayal of the academic program, residential life, student culture, expectations, and overall boarding school experience.
•Collaborate with academic and residential leadership to ensure the school's educational program and student experience are clearly communicated as central components of the school's brand and value proposition.
•Support digital outreach strategies including website engagement, social media, virtual programming, and targeted marketing campaigns.
Data & Enrollment Systems
•Use enrollment management systems and CRM tools to track inquiries, applications, and enrollment trends.
•Monitor key metrics and use data to inform strategy and decision-making.
•Develop forecasting models to support long-term enrollment planning.
•Evaluate enrollment performance across recruitment, retention, financial aid utilization, and market engagement.
Leadership & Team Management
•Lead, mentor, and supervise the admissions and residential life teams.
•Manage the retention task force.
•Establish clear goals and performance expectations for the departments.
•Encourage collaboration and professional growth within and across teams.
•Engage faculty, staff, students, parents, and alumni as ambassadors in the admissions process and beyond.

Job Requirements

Education
•Bachelor's degree required; Master's degree preferred.
Experience
•7-10+ years of experience in admissions, enrollment management, or related leadership roles.
•Direct experience working in an independent boarding school environment strongly preferred, with a clear understanding of how residential life, student support systems, and community culture influence enrollment and retention.
•Demonstrated expertise in the boarding school marketplace, including knowledge of domestic and international recruitment trends and family decision-making factors.
•Experience collaborating with student life, boarding programs, advising systems, or other aspects of the residential student experience.
•Demonstrated success in recruitment, relationship building, and enrollment strategy.
•Experience developing and implementing strategies to support student retention, re-enrollment, and long-term family engagement.
Skills & Competencies
•Strategic thinker with the ability to connect enrollment goals with institutional mission and sustainability.
•Strong analytical and data interpretation skills.
•Exceptional interpersonal and communication abilities.
•Experience with CRM systems and other enrollment and admissions management tools. Blackbaud Enrollment Management a plus.
•Ability to build strong relationships with prospective families, faculty, and external partners.
•Commitment to diversity, equity, and inclusion in enrollment practices.
•Travel required.
Personal Attributes
•Someone who thrives on teamwork, building connections, and enjoys a little laughter
•Able to juggle multiple priorities without dropping the ball
•Always looking for ways to stay ahead in a competitive landscape
•Someone who manages sensitive situations gracefully
•Someone who can inspire others

Physical Requirements:
The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodation may be made to enable individuals with disabilities to perform essential functions.
•Must have the ability to sit and stand for extended periods of time.
•Must exhibit manual dexterity to use classroom, shop and lab tools, telephone, computer, tablet or other learning device.
•Must be able to see and read a computer screen and printed material with or without vision aids.
•Must be able to hear and understand speech at normal classroom or office levels, and on the telephone.
•Must speak in audible tones so that others may understand clearly in normal classrooms, and on the telephone.
•Physical agility to lift up to 25 pounds to shoulder height and 50 pounds to waist height and to bend, stoop, sit on the floor, climb stairs, walk and reach overhead.

Working Environment:
The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions.
•Duties are normally performed in a school classroom, lab or CTE shop or classroom.
•The instructor may occasionally work in outside weather conditions and be exposed to wet and/or humid conditions, temperature fluctuations, fumes or airborne particles, chemicals commonly used in instruction and /or cleaning.
•It may be expected that the individual could be exposed to blood or other potentially infectious materials during the course of their duties.
•The teacher may be exposed to infectious disease as carried by students.
•The noise level in the work environment is usually moderate to loud on occasion.

Background Check and Fingerprinting

The Academy conducts criminal record checks on all candidates. We reserve the right to investigate fully any criminal or motor vehicle offense prior to consideration for employment. Job offer is contingent upon satisfactory maintenance or completion of our background and Child Abuse Registry reporting, and acceptance of our Sexual Harassment Policy.

St. Johnsbury Academy is an equal opportunity employer. SJA prohibits discrimination and harassment of any type and affords equal employment opportunities to employees and applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other characteristic protected by law.