Assistant Headmaster for Enrollment and Residential Life

The mission and proud tradition of St. Johnsbury Academy is to challenge our rising generation to become deep thinkers, bold creators, and responsible, compassionate members of society—always learning, and believing in their readiness and capacity to face the world and make it better. The PositionThe 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 ResponsibilitiesEnrollment LeadershipDevelop 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 & RecruitmentOversee 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 & RetentionDevelop 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 StrategyCollaborate 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 CommunicationsPartner 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 SystemsUse 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 ManagementLead, 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.Required QualificationsEducationBachelor’s degree required; Master’s degree preferred.Experience7–10+ 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 & CompetenciesStrategic 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 AttributesSomeone who thrives on teamwork, building connections, and enjoys a little laughterAble to juggle multiple priorities without dropping the ballAlways looking for ways to stay ahead in a competitive landscapeSomeone who manages sensitive situations gracefully