to Conduct Comprehensive Leadership Searches

The Assistant Head of School is a senior leader and highly visible community leader who works in close partnership with the Head of School and senior leadership team to advance the School’s mission, strategic priorities, and institutional well-being. This role emphasizes shared leadership, cross-divisional alignment, and support, development, and oversight of highly effective Academic and External Affairs teams.

The Boys’ Latin School of Maryland, the Mid-Atlantic’s oldest K – 12 school for boys, with a residential life program from students in grades 9 – 12, seeks an experienced and dynamic leader to serve as Director of Development, to begin July 2026. Reporting to the Headmaster, the Director of Development is responsible for providing strategic leadership for all facets of institutional fundraising, campaign planning and implementation, and alumni affairs.

The Director of Development will establish and articulate all fundraising strategies; oversee the identification, cultivation, solicitation, and stewardship of donor prospects; oversee all development activities; and act as a liaison for the School and the community.

We are seeking a visionary and dynamic Director of Strategic Communications and Marketing to lead this effort. This role will shape and share Wesley Prep’s market differentiators, strengthen our brand, and engage both internal and external audiences with clarity and purpose. With strong momentum and a collaborative culture, this is a unique opportunity to lead communications at a school that is growing and thriving. The Director will develop and execute a comprehensive communications strategy to elevate the School’s visibility, support enrollment and development goals, and connect with students, families, alumni, and the broader community.

The Director of Enrollment Management is a key member of the school’s leadership team, responsible for setting the vision and guiding the implementation of a comprehensive enrollment program. As the school enters a period of planned growth, the Director will help shape and scale enrollment efforts that support expansion while maintaining academic quality and a strong sense of community. The Director oversees admissions, retention, and financial aid and manages a team dedicated to building an engaged, mission-aligned student body. This role is central in advancing the school’s learning culture through a strong commitment to its mission and core values, and partners closely with academic and operational leadership to align enrollment strategy with financial goals.

The Director of Teaching and Learning is the senior PK–12 academic leader who oversees and advances the school’s academic program by developing and instituting school-wide systems that utilize Best Practices to enhance the already high quality teaching at Ellis. The Director ensures that curriculum, instruction, assessment, and use of technology are aligned across divisions, responsive to the developmental needs of girls. Working closely with Division Heads, Department Chairs, the Director of Technology, and student-support teams, the Dean leads curriculum design, promotes faculty growth, and plays a central role in shaping a cohesive, sequential, inclusive, and excellent PK–12 learning experience.

The Director of Student Affairs is involved in all aspects of shaping the student experience and community culture at Cushing Academy. The position provides leadership to the Office of Student Affairs and works with the full array of Cushing constituents. The Director leads in direction and programming for: Residential Life, Attendance, Discipline, Student Activities, Well-being, and Student Government. The Director serves as a strategic partner to the CFOO in the oversight and programming of Safety and Security, Health and Wellness, and Food Services.

The Director of Athletics and Afternoon Activities leads and administers the interscholastic and noncompetitive athletic programs of The Webb Schools. The Director of Athletics and Afternoon Activities is responsible for the daily operation of the athletic and afternoon activity program, while also assuming leadership for advancing athletics and our program in keeping with the schools’ mission.

The Brand Strategist & Senior Director of Marketing and Communications leads the development and implementation of a unified brand and communications strategy that elevates the school’s visibility, enhances its reputation, and advances institutional priorities across admissions, advancement, and community engagement.

This position ensures that the school’s story, mission, and values are authentically represented across all platforms and materials. The Senior Director will collaborate closely with creative agencies, internal partners, and key departments to manage marketing campaigns, design strategy, and the rollout of new brand assets. The Senior Director will report to the Head of School.

The Frederick Gunn School, a co-educational boarding and day school serving students in grades 9-12 and post-graduate, seeks a Chief People Officer (CPO) to join its Senior Leadership Team. The CPO will lead all aspects of the school’s people strategy and human resources function, ensuring that faculty and staff thrive in a culture rooted in trust, growth, and inclusion.

As a strategic partner to the Head of School and senior leaders, the CPO will oversee recruitment, employee relations, compensation and benefits, compliance, and organizational development. This leader will also drive initiatives in leadership development, faculty and staff growth, and the design of equitable systems that align with the school’s mission and values.

The Canterbury School of Florida is seeking a Head of Upper School for the 2026-2027 school year. Canterbury is a co-ed, Episcopal school in St. Petersburg, FL, serving students in Pre-Kindergarten through Grade 12. The Upper School Head is the educational and administrative leader of the upper division (Grades 9 - 12) with responsibility for the students, faculty, programs, and parent relations. The Head of Upper School reports directly to the Head of School and sits on the Executive Team. The Head of Upper School enjoys the support and benefits of working with an experienced, talented, cohesive, and dedicated faculty. The next Upper School Head will have the opportunity to help shape an exciting and creative future for the program while building upon a tradition of success and excellence.

At The Benjamin School, we believe that good teachers set high standards for their students and do everything they can to help them achieve them. We are looking for teachers who will help our students become self-directed, independent learners with superior academic and collegiate skills.

We are seeking an Upper School Admission & Enrollment professional who works directly with families throughout the admission process. The individual in this position must be able to work independently and collaborate with members of the Admissions team and other faculty members.

Annie Wright Schools seek a dynamic and experienced Upper School Learning Support Director to lead the design, coordination, and delivery of learning support services across grades 9 through 12. The Director provides strategic vision and daily oversight for the learning support program, ensuring that students with a range of learning profiles are known, understood, and supported to achieve their fullest potential. The Learning Support Director supervises the Upper School learning support team, which includes a learning specialist, a math specialist, and an accommodations manager.

Castilleja seeks an experienced and enthusiastic enrollment leader who will serve as a partner to the Head of School and advance the strong work of the existing Admission team, focusing on a strategic approach to recruitment and admission as the school prepares to increase enrollment in the coming years. The successful candidate will embrace the opportunities in a school culture that is dynamic, energetic, and innovative.

The Assistant Head of School is a key member of the senior leadership team, guiding the academic and co-curricular life of the school. In partnership with the Head of School, faculty, and staff, the Assistant Head of School plays a central role in sustaining and advancing the school’s educational mission. They oversee the alignment and coherence of curriculum and pedagogy, cultivate a culture of professional excellence and learning among faculty, and support student success and well-being. A visible and approachable presence, the Assistant Head builds trust across constituencies, offers thoughtful guidance, and acts as a bridge between strategic vision and day-to-day implementation. This newly formed position will support the division heads in executing the academic program, managing the implementation of professional development, and overseeing accreditation.

The Director of Enrollment Management advances the mission and vision of University Liggett School by leading a strategic, data-informed, and relationship-driven enrollment program that reflects The Liggett Approach. The Director ensures that every interaction with prospective and current families embodies the School’s commitment to academic excellence, innovation, and community. The Director of Enrollment Management will support an atmosphere of trust and openness among employees, students, and parents and will support an atmosphere that fosters the intellectual, social, physical, behavioral, and emotional growth of each student.

Wyoming Seminary, one of the oldest continuously coeducational day/boarding schools in the mid-Atlantic states, seeks a dynamic and visionary Head of the Upper School to lead its vibrant 9-12 division. Nestled in the heart of Northeast Pennsylvania, Sem has been a pillar of education in this historic corner of Pennsylvania since 1844, blending rich tradition with forward-thinking innovation. Sem’s mission is to “inspire students to lead lives of integrity, purpose, and excellence” and this important leadership role offers an exciting opportunity to shape a community where students from diverse backgrounds thrive academically, socially, and personally, preparing them to succeed and serve in the world beyond the pathways of Wyoming Seminary.

The profile of the successful candidate will include 7+ years of experience in the Human Resources function of an educational organization. An accomplished track record of successive increases in responsibility within the Human Resources area including payroll, compensation planning, recruiting, performance management programs and benefit program administration. Advanced industry certification preferred. The position requires broad knowledge of the various facets of HR in an educational organization. Confidentiality, compassion and high expectation of professionalism are the minimum requirements for this position. Excellent interpersonal, organization and communication skills are expected.

The Director of Middle School provides visionary instructional and operational leadership for the division, ensuring exceptional academic outcomes, faculty excellence, and alignment with the School’s mission and strategic goals. As the instructional leader and a member of the Senior Leadership Team, the Director oversees curriculum, faculty development, student support, and daily operations while partnering with families and colleagues to advance institutional priorities.

The Director of Financial Assistance and Institutional Reporting supports enrollment and retention goals through data management, systems oversight, and collaboration with admission and business office leadership. This position ensures the accuracy, efficiency, and integrity of admission and financial assistance operations from inquiry through enrollment and beyond.

For the academic year 2026-2027, Blue Ridge School seeks a Science Department Chair. The role of Science Department Chair is a full-time, 9 month, position that has primary responsibilities to plan, organize and implement an appropriate instructional program in a learning environment that guides and encourages students to develop and fulfill their academic potential. Beyond their core teaching role, Department Chairs serve as a communication liaison between faculty and administration, serve as a leader in curriculum and pedagogy in their respective department, and assists in hiring, training, evaluating and supporting faculty members in their respective departments. Department chairs work collaboratively with each other and their team to communicate the wider mission of the school, and serve as an advocate for their departments best interests. This person would be required to teach 4 sections of science each day in a combination of courses that could include Physics, Honors Physics, or AP Physics.

The Chief Advancement Officer (CAO) is a key member of Khan Lab School’s senior leadership team, reporting directly to the Executive Director and serving as a strategic partner in sustaining and growing the school’s innovative mission. This pivotal role combines development leadership, enrollment strategy, marketing vision, and community engagement to ensure KLS has the resources and community support needed to reimagine education for the future.

The Assistant Head of School is a key member of the senior leadership team, guiding the academic and co-curricular life of the school with a student-centered and community-minded approach. With reach across all divisions, departments, and programs, this leader champions the intellectual, artistic, and physical growth of students while fostering a culture of collaboration, curiosity, and inclusion.

The Director of Marketing and Communications is a senior leadership position responsible for developingand executing comprehensive marketing, communications, and brand strategies while overseeing all institutional messaging, campaigns, and analytics. Balancing high-level strategic leadership with focused operational execution, the Director ensures that marketing serves as a mission-critical driver of enrollment, philanthropy, community engagement, and overall institutional visibility.

Madeira is seeking a Major Gifts Officer who is a highly skilled and collaborative relationship builder and a strong communicator to serve as an active member of the Advancement Office. Reporting to the Director of Major and Planned Giving, the Major Gifts Officer plays a key role in advancing Madeira’s philanthropic goals by managing individual relationships through the donor life cycle with a comprehensive ask (annual, major, planned gifts) using a moves management system. This position works independently and collaborates extensively with colleagues within Advancement and throughout Madeira.

The Intermediate School Division Head provides strategic and day-to-day leadership for the Intermediate School program, working in close partnership with the Head of School and senior leadership team. This role oversees all aspects of the academic program, student life, and faculty leadership, ensuring alignment with Seattle Country Day School’s mission, values, and inquiry-based educational philosophy. The Division Head supports students’ academic, social, and emotional development; leads, mentors, and evaluates faculty; partners with families; and collaborates across divisions to ensure curricular continuity and a cohesive school experience.

The Head of Middle School will create a vision for and orchestrate the continuing evolution of the Middle School to ensure that the educational program, in all its facets, remains vital, engaging, and relevant. The ongoing success of the division will be the primary responsibility while cultivating the skills, habits, and practices necessary to unlock student and faculty potential for carrying forward Brookstone’s mission.

The Director of Enrollment is a member of Canterbury’s executive leadership team, reports to the Head of School, and serves as a primary ambassador for the school’s mission, culture, and distinctive programs. This role is responsible for the full arc of the student enrollment journey—from first inquiry through matriculation and beyond—and plays a vital role in sustaining the health and vitality of our school community through both thoughtful recruitment and purposeful retention.

At Cushing Academy, we believe that teaching and learning are relational. The Director of Teaching and Learning serves as an integral part of the academic leadership, under the direction of the Director of Academic Affairs, supporting and advancing institutional efforts to develop curious, creative, and confident learners and leaders. The Director of Teaching and Learning engages with multiple audiences, including both current and prospective students, families, and faculty in the delivery of Cushing’s academic programs and services. This leader works to foster positive and productive partnerships and is responsible for providing vision and direction as it relates to the design, development, and evaluation of the curriculum and instructional programs, which may include occasional night and weekend work. Cushing Academy exists for students and is seeking an experienced administrator who is excited to join an academic environment committed to inclusive design to support a range of learners, working to spark joy and curiosity in our students.

The Director of College Counseling leads the school’s comprehensive college counseling program, providing vision, strategy, and day-to-day oversight to ensure each student receives personalized guidance throughout the college search and application process. This role supervises and mentors the college counseling team, collaborates with faculty, advisors, and administrators to align academic planning with college goals, and actively builds relationships with colleges and universities to enhance opportunities for students. Importantly, the Director maintains a reduced student caseload to remain closely connected to the student experience, model best practices in counseling, and provide informed leadership to the team.

Reporting to the Head of School and serving on the senior leadership team, the Director of Enrollment Strategy provides strategic leadership for all enrollment efforts, ensuring alignment with GSB’s mission, values, and institutional priorities.

This is a moment of opportunity and forward momentum. With a new Head of School and a clear, forward-looking strategic framework, GSB is poised to strengthen its enrollment strategy, expand its reach, and deepen engagement with families. The Director of Enrollment Strategy (DES) will play a critical role in the School’s continued forward movement, serving as a key partner to the Head of School while shaping how GSB attracts, enrolls, and retains students in a competitive marketplace. This role is strategic, visible, and relational, providing senior leadership that unites teams and fosters excellence across the school.

The Director of Development and Communications is responsible for planning, leading, and executing all fundraising, advancement, marketing, and communications strategies for The Pilot School. Reporting directly to the Head of School, the Director serves on the Senior Leadership Team and works closely with the Board of Trustees, faculty, staff, families, and external partners to ensure the school’s long-term financial sustainability and the strength and clarity of its mission-driven messaging.

The Director oversees all development functions typical of an independent school, including annual giving, major gifts, donor stewardship, events, and advancement operations. In addition, the Director leads all communications and marketing efforts, serving as steward of the school’s brand, voice, and public presence. While some marketing functions—primarily digital marketing—are supported through an external firm, the Director maintains strategic oversight and accountability for all messaging, campaigns, and outcomes.

The Long Ridge School seeks a Director of Finance to join our leadership team and serve as a strategic and trusted partner to the Head of School and Board of Trustees. This role is central to the school’s financial health, responsible operations, and future planning.

Reporting to the Head of School, the Director of Finance oversees the school’s financial systems and business operations, including budgeting, accounting, payroll, benefits, human resources administration, and risk management. This is a senior leadership position that works closely with the Board, faculty, staff, families, and external partners.

This role is ideal for a collaborative, steady, and solutions-oriented professional who enjoys both strategic thinking and hands-on financial management within a close-knit school community

The Associate Director of Development Operations plays a central role in the successful execution of the School’s campaign and serves as the operational backbone of campaign activity within the Development Office. Reporting to the Director of Development, this position is responsible for managing the campaign’s prospect pipeline, coordinating volunteer and leadership engagement, and ensuring that campaign activity is executed and advanced according to established timelines.

This role is highly project management-driven and requires someone who can work independently, manage up, and thrive in the nuance and complexity of an independent school environment. The Associate Director of Development Operations is accountable for translating strategy into action- ensuring that plans are executed, meetings are productive, follow-ups occur, and progress is visible and measurable.

The Lower School Director is a key member of Khan Lab School’s leadership team, reporting directly to the Executive Director and serving as a mastery-based learning visionary who inspires students and staff alike. This pivotal role combines academic and operational leadership with a passion for reimagining education, requiring a technically savvy, hands-on player-coach leader with proven experience as an academic leader in innovative school environments who actively supports both teachers and students through direct engagement—whether teaching a class, leading an advisory group, or conducting classroom observations. The ideal candidate will bring exceptional creative problem-solving skills and adaptability to develop personalized educational pathways, coupled with outstanding communication abilities to engage effectively with students, parents, and faculty.

The Chair of the Science Department provides instructional coaching for departmental faculty and is responsible for the development and implementation of an aligned sequencing of science coursework. Collaborating with the Assistant Head of School, Dean of Studies, and Division Heads, the Chair will lead the development and delivery of a mission-aligned curriculum that emphasizes “doing science” through phenomena-based learning and the engineering design process. A key priority for this role is to operationalize the findings of the School’s ongoing STEM review, specifically by using engineering design as the “connective tissue” between disciplines and ensuring that inquiry-based investigation becomes the norm across all divisions.

As a key member of the School’s administrative team, the Assistant Head of School and Head of Middle School will support the mission and vision of University Liggett School through positive interaction with students and faculty. The Assistant Head of School and Head of Middle School will collaborate closely with the Head of School and senior administrators to advance all-school initiatives, support faculty growth, and ensure programmatic coherence across divisions. Specifically, it is the Head of Middle School’s responsibility to ensure that the school’s mission, vision, and core values are the center of all decisions and actions within the division. The Head of Middle School will support an atmosphere of trust and openness among teachers, students, and parents, and will support an atmosphere that fosters belonging and the intellectual, social, physical, behavioral, and emotional growth of each student.

The Head of Student Support (HOSS) is the educational and administrative leader for student support services across Pre-Kindergarten through Grade 5. This role designs, facilitates, and monitors a developmentally responsive, prevention-oriented system that builds staff capacity and ensures early identification and intervention for academic, social-emotional, and behavioral needs. The HOSS partners closely with the Head of Elementary, Head of Early Childhood, and Educational Leadership Team (ELT) to ensure student support practices are equitable, compliant, and sustainable, aligning with the IB PYP philosophy and the mission of the International School of Portland.

Baylor School is hiring for the full-time position of Research and Instructional Librarian in the Hedges Library to begin in the 26-27 school year. The highly qualified candidate will have proven experience in libraries, a record of working with students in grades 6-12, and a bachelor’s degree in Humanities or Information Science, and an MLS, MLIS, or MSIS degree. Demonstrated experience with research instruction, facility with Springshare LibGuides, and an ability to connect with students are a must. The Research and Instructional Librarian will collaborate with students and faculty to support course-specific curriculum through research instruction and will work to create a warm, welcoming library environment.

Fredericksburg Academy is seeking a new Head of Lower School for the 2026 year and beyond (start date can be sooner if candidate is available). The Head of Lower School is responsible for providing leadership, development, and support for instructional, curricular, behavioral, and support systems. The position administers and manages the divisional budget and supervises all Lower School faculty, staff, and students. In order to create a dynamic learning environment, the Head of Lower School is charged with the responsibility of all curricular, non- curricular, life skills development and activities involving students and faculty of the Lower School. In addition, the division head oversees the recruitment, hiring and supervision and evaluation of the Lower School’s instructional staff and support personnel.

The DHR reports to the Associate Head of School for Finance and Operations and works in close partnership with the Head of School. As a member of the School Leadership Team, the Director plays a key role in advancing a cohesive, people-centered strategy aligned with Alcuin’s mission and vision. The DHR will provide leadership across all facets of employee experience, including workforce planning, recruitment and retention, compensation and benefits, performance management, professional growth and development, and employee relations. Partnering closely with the School Leadership Team, faculty, and administrative and operations staff, the Director will help cultivate a supportive, inclusive, and high-performing workplace culture that reflects Alcuin’s values—one that honors the dignity of each individual, encourages continuous learning, and supports excellence and confidence in teaching and operations.

The Director of Learning Support plays a lead role in ensuring that the Manzano Day School academic program meets the needs of the broad range of learners comprising the student body by overseeing student support processes and plans and working directly with students, families, and teachers. The Director of Learning Support works with the Academic Administration, Student Support Team, and faculty to create a school environment where children thrive, promoting the academic, social-emotional, behavioral, and physical well-being of students in grades pre-k through fifth grade and empowering learners at all levels. This includes coordinating services for students, identifying students who need support, both intervention and extension/enrichment, and working with our faculty to provide a learning experience that effectively reaches all learners. This role provides leadership, strategic direction, and oversight, fostering collaboration among teachers and families and assuring alignment with the school’s mission and academic goals.

Mount Saint Joseph Academy, a Roman Catholic college preparatory school for young women, seeks an innovative and relationship-centered leader to serve as its inaugural Director of College Counseling and Experiential Learning. This newly created position reflects the Mount’s commitment to preparing students not only for college admission, but for lives of purpose, leadership, and service beyond graduation. Reporting directly to the Principal, the Director will provide strategic leadership for the college counseling program while building new initiatives that connect students with alumnae mentors and real-world professional experiences. The ideal candidate is both a skilled college counselor and a visionary program builder—someone who can carry a counseling caseload while developing the infrastructure for experiential learning opportunities that prepare young women to thrive.

This is a full-time, year-round, exempt administrative position. Reporting directly to the Head of School, the Lower School Director is an integral member of the school’s leadership team. They are particularly responsible for overseeing the quality of instruction and academic programming in the Lower School, with a focus on strong foundations in mathematics, literacy, world language, and the Arts. The ideal candidate would combine a strong understanding of student-centered pedagogy with an understanding of the importance of Saint Stephen’s Episcopal School’s (SSES) traditions.

The Director of Enrollment Management at CWA will have the opportunity to build upon the school’s strong reputation and deeply relational culture while navigating an increasingly competitive and dynamic independent school landscape. With a compelling mission, a beautiful campus, and a comprehensive Preschool–12 program, CWA is well positioned to strengthen enrollment, elevate its brand, and broaden its reach throughout the Puget Sound region. A key opportunity for this leader will be to further integrate enrollment management and marketing into a cohesive, data-informed strategy that clearly communicates the school’s value and differentiators to a diverse range of families.

An independent Catholic school for young women in grades 7-12, Ursuline Academy is seeking a Senior Director of Engagement and Leadership Giving. Working closely with the Chief Advancement Officer, the Senior Director of Engagement and Leadership Giving will provide strategic leadership and oversight of constituent engagement, alumnae relations, and annual giving. This role will supervise and work collaboratively with the Director of Alumnae Relations, the Director of Annual Giving, and the Director of Special Events and Community Engagement to identify and implement effective strategies to enhance constituent engagement and giving. The Senior Director of Engagement and Leadership Giving will also carry a portfolio of prospects.

The Upper School Division Director handles the overall leadership and strategic direction for the ninth through twelfth grade students and faculty at Vail Mountain School. This position will manage the day-to-day operations of the Upper School, working collaboratively with our other Division Directors and reporting directly to the Head of School.

Reporting to the Director of Annual Giving, the Assistant Director of Annual Giving plays a key role in supporting the implementation of St. Albans School’s strategy to achieve St. Albans Fund goals. This full-time, 12-month position involves assisting with donor outreach and stewardship, managing volunteer programs and events, preparing and analyzing reports to inform strategy, and collaborating with Development and alumni relations staff to cultivate strong constituent relationships. The Assistant Director also contributes to the creation of solicitations and acknowledgements, oversees accurate tracking of contributions, and participates in major department events. Additional responsibilities may be assigned as needed to support the overall success of the Development Office.

The Boys’ Latin School of Maryland invites applications for the Director of College Counseling position, beginning July 2026. The director leads the School’s comprehensive college counseling program, providing vision, strategy, and day-to-day oversight to ensure each student receives personalized guidance throughout the college search and application process. This role supervises and mentors the college counseling team, collaborates with faculty, advisors and administrators to align academic planning with college goals, and actively builds relationships with colleges and universities to enhance opportunities for students.