Richmond, Virginia
Stamford, Connecticut
Posted: 19-May-26
Location: Annapolis, Maryland
Type: Full Time
Categories:
Overview
St. Anne’s School of Annapolis seeks a dynamic, mission-driven leader to serve as its Director of Enrollment and Community. This newly named role reflects the School’s intentional commitment to not only recruiting mission-aligned families, but to deepening the bonds that make the St. Anne’s community one of Annapolis’s most distinctive and enduring.
Drawing from St. Anne’s School’s Episcopal tradition and its core values of dignity, belonging, and whole-child development, the Director of Enrollment and Community will serve as both the primary steward of the admissions pipeline and a key architect of parent engagement and family retention. The Director reports directly to the Head of School and serves as a member of the Leadership Team, partnering closely with Program Heads, Advancement team, and the CFO.
What Makes This Role Distinctive
At St. Anne’s School, admissions is understood as the beginning of a relationship—not a transaction. The addition ‘Community’ to this title signals a genuine organizational commitment: the Director will be charged with cultivating the loyalty, belonging, and advocacy of current families with the same care and intentionality they bring to attracting new ones. Specifically, this means:
- Serving as a proactive partner to the Parents Association and school
leadership on family engagement initiatives throughout the year - Building systems for listening to and acting on family feedback, transforming
insight into institutional improvement - Identifying at-risk attrition early and working collaboratively with Program
Heads to address family concerns before they result in departure - Mobilizing current families as authentic ambassadors and word-of-mouth
advocates for the School
Mission
St. Anne’s School of Annapolis invests in the intellectual and spiritual promise of each student in
a community that celebrates diversity and upholds the dignity of every human being. We challenge students to think critically and creatively, to know themselves as learners, and to govern their lives with confidence, compassion, and integrity.
About St. Anne’s School
Founded in the spirit of its Episcopal tradition, St. Anne’s School of Annapolis is an independent, co-educational school serving students from age two through Grade 8. Nestled on the waterfront shores of the Chesapeake Bay at 3112 Arundel on the Bay Road, St. Anne’s occupies a unique place in the fabric of Annapolis: small enough that every child is known, ambitious enough that every child is challenged, and rooted deeply enough that its graduates carry the
School’s values with them for a lifetime. Director of Enrollment and Community
St. Annes School is guided by a mission to invest in the spiritual promise of each student in a community that celebrates diversity and upholds the dignity of every person. That mission is lived out every day in classrooms led by extraordinary educators, on athletic fields where character is built alongside competition, and in the hallways where a culture of belonging is cultivated intentionally and joyfully.
The School’s academic programs span three divisions: a Program for Young Children (Twos–PreK), a Lower School (K–Grade 4), and an Upper School (Grades 5–8). Signature programs, a Center for Learning, robust athletics, and extended day offerings round out an experience that prepares students not just for high school, but for life. St. Anne’s graduates attend some of the most selective independent high schools in the region and beyond.
The current school theme, Growing in Gratitude, reflects a community that pauses to appreciate what it has built—and what it is still becoming.
About Annapolis
Annapolis is one of America’s most storied small cities—home to the U.S. Naval Academy, the Maryland State House (the oldest state capitol still in continuous legislative use), and a bustling harbor where sailboats outnumber parking spots. With cobblestone streets, nationally recognized dining, a thriving arts community through the Annapolis Arts District and Maryland Hall for the Creative Arts, and world-class access to the Chesapeake Bay, Annapolis offers an exceptional quality of life.
The city sits just 30 miles from both Washington, D.C., and Baltimore, making it a convenient hub for families and professionals alike. For those who love the water, the outdoors, history, and the energy of a close-knit community, Annapolis is a rare find.
The Opportunity
St. Anne’s School is at an exciting inflection point. Enrollment is healthy, the School’s reputation among Annapolis families is strong, and a passionate parent community has become one of the School’s greatest assets. At the same time, independent school enrollment nationally demands increasingly sophisticated and relationship-centered approaches—and St. Anne’s is ready to invest in exactly that.
The newly named Director of Enrollment and Community role reflects that investment. This is not a rebranding exercise. It is a genuine expansion of scope—a signal to the incoming leader and to the St. Anne’s community that enrollment opportunities and deepening family loyalty are two sides of the same coin. The School’s next great admission leader will be someone who finds equal energy in greeting a prospective family on their first campus tour and in gathering current parents around a shared table to celebrate their children.
This is a senior leadership position with direct access to the Head of School, meaningful influence over institutional strategy, and the opportunity to shape a community that will feel the effects of this work for years to come.
Key Responsibilities
Admissions & Enrollment Management
- Direct all aspects of the admissions process from initial inquiry through enrollment, including tours, interviews, screenings, and final decisions
- Chair the Admissions Committee and maintain comprehensive applicant portfolios and weekly enrollment dashboards tracking inquiries, applications, tours, and conversions
- Develop and execute enrollment strategies aligned with the School’s mission, tuition goals, and demographic aspirations
- Partner with the CFO to administer the Tailored Tuition program and coordinate financial assistance communication with prospective families
- Coordinate with Program Heads on re-enrollment processes, maintaining ongoing awareness of attrition trends and intervening proactively
- Prepare and interpret enrollment statistics—including diversity, geographic distribution,
matriculation, and retention data—for the Head of School and Board of Trustees
Family Engagement & Community Building
- Design and lead new family orientation experiences, including spring communications with newly enrolled families, organized playdates, new parent receptions, buddy family programs, and new family surveys
- Serve as a primary point of connection for current families, maintaining an accessible, warm
presence that reinforces their confidence in and affinity for the School - Partner with the Parents Association, Program Heads, and the Leadership Team to develop
retention strategies that foster belonging and satisfaction among enrolled families - Conduct and analyze community surveys, exit interviews, and family feedback to identify
opportunities for improvement; bring findings to leadership with actionable recommendations - Identify at-risk retention situations in collaboration with Program Heads and faculty, developing thoughtful, timely outreach to families navigating transitions or concerns
Marketing, Outreach & Events
- Work closely with the Director of Communications and Marketing to develop and execute compelling recruitment messaging, digital content, and collateral for prospective families
- Coordinate and lead admissions events including open houses, admissions fairs, shadow visit days, and applicant assessment days
- Cultivate relationships with feeder schools, nursery programs, neighborhood associations, and community organizations that connect St. Anne’s with prospective mission-aligned families
- Maintain and grow membership and engagement with NAIS, NAES, and AIMS regional networks
- Act as a compelling, gracious ambassador for St. Anne’s across Annapolis and the broader region
Data Management & Reporting
- Maintain accurate and complete records for all prospective students and applicants in the School’s admissions management system
- Generate regular enrollment reports and trend analyses for the Head of School and Board of Trustees
- Evaluate the effectiveness of recruitment and retention efforts through data collection and adjust strategies accordingly
- Design and administer community surveys, exit surveys, and applicant-experience surveys to build institutional knowledge over time
Leadership & Collaboration
- Serve on the Leadership Team, reporting directly to the Head of School and contributing to the School’s strategic planning and institutional priorities
- Partner with the Advancement Team to support advancement events and outreach that strengthen the broader St. Anne’s community
- Collaborate with the DEIB coordinator and leadership to ensure the admissions process is welcoming and accessible to families from all backgrounds
- Represent St. Anne’s with professionalism and warmth at evening and weekend events as needed
What You Will Do
Welcome Families In
You will be the face of St. Anne’s School to the families considering a life-changing decision. You will guide them through the admissions journey with warmth, clarity, and authenticity—ensuring every prospective family feels genuinely seen and understood, not processed. You will chair the Admissions Committee, manage the full admissions cycle, and lead events that bring St. Anne’s School to life for families still deciding.
Deepen Roots with the Families Already Here
Retention begins with relationship. You will work alongside Program Heads and faculty to identify and support families navigating challenges, and alongside the Parents Association to build programming that strengthens community connections. You will gather feedback systematically—through surveys, conversations, and exit interviews—and translate what you learn into actionable recommendations for the leadership team. When families feel genuinely heard, they stay. When they stay, they bring others.
Build the Pipeline
You will maintain and grow the School’s relationships with Annapolis-area feeder schools, nursery programs, neighborhood associations, and community organizations. You will partner with the Director of Communications and Marketing to tell St. Anne’s story compellingly across digital and traditional channels. You will take the School’s mission on the road to admissions fairs and community events, representing St. Anne’s with the same energy and excellence the School brings to everything it does.
Lead with Data
You will maintain rigorous records, generate regular enrollment reports for the Head of School and Board of Trustees, and use data to continuously sharpen the School’s enrollment strategy. You will design and administer community surveys and applicant-experience instruments that give St. Anne’s a longitudinal view of what is working and what can be better.
Serve on the Leadership Team
You will bring an enrollment and community perspective to the School’s senior leadership
conversations, contributing to strategic planning and institutional initiatives. You will partner with the Head of School to align advancement and enrollment goals. You will be a connector, a collaborator, and a trusted voice at the table.
The Ideal Candidate
St. Anne’s is looking for a relationship-builder who is also a strategic thinker—someone who can hold a warm conversation with a nervous parent at an open house and build a data-driven enrollment strategy with the same ease. The ideal candidate brings:
- Genuine passion for mission-driven education and authentic alignment with St. Anne’s School’s values of dignity, belonging, and whole-child development
- Experience in independent school admissions or enrollment management, with familiarity with the AIMS/NAIS independent school community as well as the Annapolis market strongly preferred
- A relational, community-oriented style—someone who finds deep satisfaction in the long arc of a family’s relationship with a school, not just the enrollment transaction
- Strong written and verbal communication skills and the ability to represent the School authentically and compellingly to diverse audiences
- Organizational rigor and the ability to manage a complex admissions calendar without losing sight of the human beings at the center of every interaction
- Comfort with enrollment data and technology platforms (e.g., Blackbaud, Google Workspace) and a data- informed approach to strategy and decision-making
- A collaborative spirit and the emotional intelligence to work across a close-knit school community with grace and discretion
- Commitment to diversity, equity, inclusion, and belonging as essential—not optional—values in an enrollment program
Qualifications
- Bachelor’s degree required; advanced degree in education, communications, nonprofit management, or a related field preferred
- Meaningful experience in independent school admissions, enrollment management, or a closely related field; familiarity with the AIMS/NAIS independent school community strongly preferred
- Demonstrated track record of building relationships across diverse constituencies—families, faculty, administrators, and community partners
- Excellent written and verbal communication skills, with the ability to represent the School persuasively and authentically in a wide range of settings
- Experience with admissions management software (e.g., Blackbaud) and proficiency with Google Workspace and standard digital communication platforms
- Strong organizational skills and the ability to manage multiple priorities across the admissions cycle with attention to detail and follow-through
- A collaborative, team-oriented spirit and a genuine passion for the School’s mission: investing in the spiritual promise of each child in a community that celebrates diversity and upholds the dignity of every person
- Cultural competency and demonstrated commitment to diversity, equity, inclusion, and belonging in educational settings
How to Apply
Educational Directions is assisting St. Anne School of Annapolis on this search. Interested candidates should send a resume, a letter of interest, a statement of educational and leadership philosophy, and a list of three (3) professional references to the search consultant, Highley Thompson, at Highley.Thompson@edudx.com.
Please do not contact the School directly.
St. Anne’s School is deeply committed to building and sustaining a diverse, inclusive school community. We strongly encourage candidates who bring a variety of backgrounds, perspectives, and lived experiences to apply. The School’s DEIB work is ongoing, collaborative, and central to our identity—the Director of Enrollment and Community will be both a partner in and a champion of this work.
