to Conduct Comprehensive Leadership Searches

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.

Austin International School seeks a strategic and relationship-focused Director of Institutional Advancement to advance the mission of our school within the Austin community and lead comprehensive fundraising efforts. This solo advancement professional will work collaboratively with the executive leadership team to build philanthropic support, strengthen community partnerships, and enhance the school’s visibility and impact. This is an exceptional opportunity for a development professional who thrives in an entrepreneurial environment and is passionate about independent education.

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.

Saint Thomas’ Episcopal School employs individuals who are committed to upholding our mission of forming honorable men and women through a classical education grounded in a Christ-centered worldview. All faculty are expected to understand and promote the mission, standards, and policies of the School. 

We are seeking a passionate and dependable Head of Lower School to join our team. Responsibilities will include, but are not limited to, overseeing the educational programs and day-to-day operations of the Lower School at Saint Thomas’ Episcopal. This position will require an individual who is able to handle a wide range of responsibilities, including administrative tasks.

Powhatan School seeks an experienced and collaborative educational leader to serve as Head of Middle School (Grades 6–8), beginning July 2026. This is a full-time, 12-month senior administrative position reporting directly to the Head of School and serving as a key member of the senior leadership team.

The Head of Middle School is responsible for the overall leadership and daily operation of the Middle School, which serves approximately 85 students and is supported by 15 dedicated faculty members. The Division Head oversees academic programming, student life, faculty support and professional development, parent communication, and all aspects of the Middle School experience that foster a joyful, engaging, and supportive learning community.

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.

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.

Our dynamic, innovative school is looking for a new Upper School Principal to begin July 1, 2026. The Upper School Principal is a visionary, student-centered educational leader who oversees all aspects of the Upper School program (Grades 9–12) such as curriculum, instruction, faculty development, student support and discipline, program innovation, student-facing administration and staff, and the overall school culture.

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 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.

Cheshire Academy seeks a dynamic and strategic leader to serve as its inaugural Dean of Enrollment Management. This newly established role reflects the school’s commitment to a holistic, institution-wide approach to enrollment that goes beyond traditional admission functions. The Dean of Enrollment Management will provide senior-level leadership, guiding enrollment strategy across the institution and serving as a key member of the senior leadership team with broad cross-functional responsibilities.

The Director of Leadership Giving is a senior advancement professional responsible for cultivating and securing transformational gifts that support Wakefield School’s strategic priorities, including the multi-phase Campus Master Plan and forthcoming capital campaign. With primary responsibility for principal gifts, the Director builds and sustains high-impact relationships with the school’s most generous and engaged supporters.

Reporting to the Head of School, the Director works in close partnership with the Board of Trustees, the Advancement Team, and key volunteer leaders. This leader drives the strategy and execution behind the school’s most significant philanthropic opportunities.

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, Campaign 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, Campaign 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.

Beginning in July 2026, the new Head of Lower School will lead this division in providing a nurturing and developmentally appropriate learning environment for students in Kindergarten to Grade 4. With the appointment of a new Head of School in 2018 and a transformational building project on the horizon, Trinity School is in the midst of a new chapter in its growth and development. This is an exciting time in Trinity School’s history for the next Head of Lower School to help shape the School’s vision for the future.

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.

EF Academy, New York, an international boarding school Grades 9-12, located in beautiful Westchester County, just a short trip from the heart of NYC, is seeking a Deputy Head of School Academics. This role will report directly to the Head of School and serve as a key member of the Senior Leadership Team (SLT). This role provides visionary academic leadership and strategic oversight for all aspects of teaching, learning, and curriculum at EF Academy.

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. The Director of Development serves on the School’s administrative leadership team, works directly with the Board of Trustees, and is responsible for the management and mentoring of the alumni and development office, as well as coordinating with other school departments, such as enrollment management and marketing and communications.

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. For a creative communicator ready to capture the joyful energy of our classrooms, the spirit of our community, and the impact of a Wesley Prep education, this is an extraordinary opportunity to make a lasting impact.

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 Chief Advancement Officer (CAO) plays a pivotal role in advancing this mission by providing strategic leadership and oversight for all aspects of the school’s revenue generation, community engagement, and external relations. A member of the Senior Leadership Team and reporting directly to the Head of School, the CAO leads an integrated Advancement team encompassing Development, Enrollment Management, Marketing, and Community Engagement.

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.