to Conduct Comprehensive Leadership Searches

Foxcroft seeks an Assistant Head of School to work in partnership with its newly installed Head of School, Dr. Lisa Kaenzig. Dr. Kaenzig spent more than twenty years as a college dean of women with a national reputation for her work with women leaders.

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.

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.

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 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.

This role serves as a key strategic partner to the Executive Director, leadership team, and Board of Trustees in advancing the school’s mission and ensuring financial sustainability and operational excellence. The Senior Director of Finance and Administration is responsible for managing all aspects of the school’s financial health, including strategic stewardship of the school’s financial resources, day-to-day financial operations, long-term strategic planning, oversight of risk management and all fiduciary responsibilities.

At The St. Paul’s Schools, the lower school hums with energy, curiosity and joy. In our halls, you hear giggles in the reading nook and curiosity around every corner. As an episcopal school, we merge an appetite for deep learning with a sense of wonder about the world. We ensure our students have a heartfelt concern for others and a confidence in their own abilities. Here, childhood is not rushed – it is celebrated.

The Director (Principal) of the Lower School is a member of the School Leadership Team and advances The Roeper School’s mission by leading and providing operational and academic oversight to the Lower School. The Director works under the guidance of the Head of School to implement and maintain an innovative, progressive, child-centered program for gifted learners.

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.

Reporting to the Head of School, the Director of Enrollment Management is responsible for managing all facets of the admissions process in the school’s effort to attract and enroll a diverse and dynamic student population and mission-aligned families. The Director of Enrollment Management ensures the long-term health of the student body and broader alumnae base by coordinating the tracking of prospective students from applicant to enrollment and beyond (admission), the analysis of data that affect enrollment (research) and the marketing efforts to attract new families to the school. It is their responsibility to anticipate the threats and opportunities that can impact Castilleja’s short- and long-term institutional enrollment goals, which are determined in conjunction with the Head of School and the Strategic Enrollment Management Committee.

The Director of Finance and Operations (DFO) promotes the mission, standards, and policies of the School and provides leadership as these evolve and are evaluated. The DFO works strategically with the Head of School and Board of Trustees in managing the School’s resources prudently and safeguarding the School’s assets, ensuring the financial viability of the School for future generations. The DFO performs professional accounting work involving compilation, consolidation and analysis of financial data and establishes appropriate financial controls and procedures. The DFO maintains and fosters high ethical standards, integrity and respect for the school community in the conduct of the school’s business.

The DFO provides leadership and management of the School’s operating budget and finances and is responsible for the supervision, coordination, and administration of all aspects of the School’s Business Office.

The Regional Director of Admissions leads student recruitment and enrollment efforts across Connecticut (including Day and District placement) and New York State, with a particular focus on the New York City area. As the school’s primary representative in the region, this individual cultivates strong relationships with families, feeder schools, educational consultants, alumni, and community partners to achieve annual enrollment goals. The role combines outreach, travel, event planning, and application review with a focus on delivering a highly personal, mission-driven admission experience.

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.

The Director of Admissions or Director of Enrollment Management serves as a key member of the Enrollment Management team and is responsible for leading and executing a comprehensive admissions strategy to attract, engage, and enroll mission-appropriate students. Reporting to the Assistant Head of School for Enrollment and Advancement, the Director provides leadership to the admissions team, ensures operational excellence in all aspects of the admissions cycle, and serves as a passionate ambassador for The Winchendon School’s programs and values.

The successful candidate will be a skilled operator, a strategic thinker, and a relationship-builder who brings strong networks with domestic and international educational consultants. They will have demonstrated success in international recruitment and in working with families seeking a school that offers robust support for students with neurodiverse learning profiles.

The Director of Development is a frontline fundraiser responsible for developing, refining, and implementing Church Farm School’s strategy for the identification, qualification, cultivation, solicitation, and stewardship of individuals making charitable gifts to the school.

The Director of Development will oversee the annual fund, mid-level giving, society giving and engagement, and EITC/OSTC gifts under $5000. They will also lead development communications, specifically mailed solicitations, digital donor communications, and the buildout of a comprehensive stewardship strategy.

York’s distinct mission is to inspire and prepare a diverse community of creative, independent thinkers. Through robust curricular, co-curricular, and extra-curricular programs, the School strives to produce globally-minded students who solve complex problems in their current and future communities using relevant 21st-century skills.

The Chief Financial Officer (CFO) is a key member of the senior leadership team, responsible for overseeing the near and long-term financial health and strategic financial management of the school. The CFO provides financial leadership, ensuring long-term sustainability while upholding the mission, values, and strategic goals of the school. This position reports directly to the Head of School and works closely with the Board of Trustees, several of its committees  as well as and other key stakeholders.

Baker Demonstration School seeks a dynamic and innovative Director of Admissions to lead our enrollment initiatives and champion the story of one of Chicago’s best-kept educational treasures throughout the greater metropolitan area. This is an extraordinary opportunity to leverage your expertise in admissions while making a meaningful impact on the future of progressive education in one of the most prestigious communities in the region.

The Director of Athletics and Afternoon Activitiesleads and administers the interscholastic and non-competitive 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 Director of Development will lead the fundraising function at Frankford Friends School, reporting to, collaborating with, and advising the Head of School and Board of Trustees. In this role, they will create and execute strategies for the FFS Annual Fund, EITC/OSTC solicitation, and major gifts, to include multi-year fundraising plans that focus on retaining donors, expanding the donor base, and increasing gifts. In addition, they will research and prepare grant applications and required stewardship reports for foundations and contribute development content to the School’s website, blog, and publications.