Engaging with our Partners to Conduct Comprehensive Leadership Searches
Head of School Search
The IDEAL School of Manhattan seeks a new head of school to begin in the 2027-28 school year and has partnered with DovetailED to lead the search.
Read the full opportunity statement below.
Executive Opportunities
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Saint Andrew’s School | Boca Raton, FL | Assistant Head of School
The Assistant Head of School will work closely with the Head of School to provide leadership and strategic oversight of academic and co-curricular programming. This role will collaborate with academic leaders and delegate effectively to address both urgent matters pertaining to the successful delivery of the School’s mission and strategic initiatives that require a longer-term focus.
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TMI Episcopal | San Antonio, TX | Associate Head of School
TMI Episcopal seeks an accomplished, innovative, and collaborative educational leader to serve as its Associate Head of School. Reporting to the President/Head of School and serving as a member of the Senior Leadership Team, the Associate Head will provide strategic leadership for the School’s academic and signature programs.
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African Leadership Academy | Johannesburg, South Africa | Director of University Guidance
ALA’s University Guidance program supports this exceptional student population and their families as they plan and pursue successful transitions beyond ALA. In line with our leadership philosophy, students are expected to take ownership of their futures. The program equips students and parents with the information, resources, and individualized coaching needed to pursue tertiary education pathways anywhere in the world.
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Almaden Country Day School | San Jose, CA | Head of the Learning Center (TLC)
Almaden Country Day School seeks to hire the next leader of our nationally-acclaimed program, a senior administrative role equivalent to a Division Head. We seek a compassionate administrator who is certified in the Orton Gillingham Approach (at least the Clinical level) and has educational leadership and instructional coaching experience.
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Brookstone School | Columbus, GA | Director of Major Gifts
The inaugural Director of Major Gifts is a key member of the Advancement team who will play an essential role in growing philanthropy at Brookstone School. In the first year of a historic $35M comprehensive capital campaign, supporting an ambitious strategic vision for 2025–2030, the School has already secured $13M toward its goal two years into the campaign, reflecting strong community confidence and momentum.
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Carolina Day School | Asheville, NC | Key School Principal
Carolina Day School seeks a Principal of the Key School who will serve as the relational heart and instructional leader of this distinctive program — someone who finds deep purpose in leading a program that changes the trajectory of young lives.
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Catlin Gabel School | Portland, OR | Director of Human Resources
Catlin Gabel School seeks an experienced, collaborative, and mission-driven Director of Human Resources with a demonstrated track record of leading through organizational change, building trust, strengthening teams, and delivering operational excellence. Reporting directly to the Head of School, the Director will partner closely with the Chief Finance & Operations Officer, Assistant Head of School, and school leaders to shape the employee experience from recruitment through retirement.
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Columbia Grammar & Preparatory School | New York, NY | Director of Communications
Serving on the Senior Leadership Team and reporting to the Head of School, the Director of Communications will lead a dedicated two-person team that will play a crucial role in bringing CGPS’s upcoming strategic plan to life. By refining our brand narrative and crafting consistent, high-impact messaging across all channels, the Director advances key school priorities and celebrates the CGPS story.
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Columbia Grammar & Preparatory School | New York, NY | Grammar School Director
The Grammar School Director serves as the primary educational and administrative leader for Grades PK–5 at Columbia Grammar & Preparatory School, reporting directly to the Head of School. In this pivotal role, the Director fosters an inspiring, academically rigorous, and inclusive learning environment while overseeing daily divisional operations, scheduling, annual budgets, and signature programs.
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Congressional School | Falls Church, VA | Director of Advancement and External Affairs
Congressional School seeks an experienced, dynamic Director of Advancement and External Affairs to define a vision for advancement, parent and alumni relations, and implement the necessary infrastructure that strengthens a culture of philanthropy. The Director is a key member of the School’s Leadership Team and provides meaningful input on a full range of issues facing the school.
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Connelly School of the Holy Child | Potomac, MD | Head of Development
The Head of Development is a senior administrative role responsible for advancing Connelly School of the Holy Child’s philanthropic priorities and securing the financial resources necessary to support its mission and vision. Reporting directly to the Head of School, the Head of Development provides strategic vision, leadership, and execution for all fundraising initiatives, including annual giving, major gifts, capital campaigns, foundation relations, alumni engagement, and donor stewardship.
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Connelly School of the Holy Child | Potomac, MD | Head of Human Resources
Connelly School of the Holy Child, an independent Catholic school in Potomac, Maryland, seeks a strategic, collaborative, and experienced leader to serve as its next Head of Human Resources. Reporting to the Head of School and serving as a key member of the school’s leadership team, the Head of Human Resources will lead all aspects of human resources strategy and operations in support of the school’s mission, values, and community.
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Duchesne Academy of the Sacred Heart | Houston, TX | Chief Advancement Officer
Duchesne Academy of the Sacred Heart finds itself at a pivotal moment in its over 65-year history on Memorial Drive in Houston, Texas. We have completed an unprecedented campaign for a contiguous 8-acre land acquisition and are poised to chart a future that will help us meet the demand for increased admissions and enrollment, expand and enhance programming, and add and improve facilities.
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Far Hills Country Day School | Far Hills, NJ | Chief Financial Officer
The Chief Financial Officer is responsible to the Head of School and serves on the School Leadership Team. Working closely with the SLT and appropriate trustee committees, the CFO manages the resources of Far Hills Country Day School to support students and employees, enabling students to achieve success in the modern world through academic excellence and character development.
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Far Hills Country Day School | Far Hills, NJ | Director of Lower School
The Director of the Lower School reports to the Head of School and is a member of the School Leadership Team. The DLS leads a Lower School of about 87 students in PreSchool–Grade 4, helping them succeed in the modern world through academic excellence and character development.
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Foxcroft School | Middleburg, VA | Campaign Director
Foxcroft School seeks an experienced Campaign Manager/Director to oversee and work collaboratively to manage Foxcroft’s Building for Our Future campaign. The Campaign Manager/Director will report to the Director of Institutional Advancement and work in close partnership with the Head of School to oversee campaign planning and implementation.
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Francis Parker School of Louisville | Louisville, KY | Director of Enrollment Management/Goshen Campus Admissions Director
Francis Parker School seeks a Director of Enrollment Management/Goshen Campus Admissions Director, located primarily on our Goshen Campus. This position oversees all enrollment management, including financial aid and current student retention, as well as serves as the lead for Admissions on our Goshen Campus, which serves PS 2s - 8th grade.
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Gould Academy | Bethel, ME | Director of Health Services
The Director of Health Services at Gould Academy leads and manages a team of health staff, including Nurses, a School Counselor, an Athletic Trainer, and a Student Health Services Coordinator. The Director oversees the smooth operation of Health Services, ensures that the delivery of care meets high standards, supports summer camp coverage, and acts as a liaison to the wider school community.
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Green Mountain Valley School | Waitsfield, VT | Director of Development
At GMVS, we’re more than just a training ground for future champions; we’re a community that shares an undying passion for the sport. Join us, and your impact will be immediate and profound. Your role will define the future of ski racing by ensuring that every aspiring athlete gets the opportunity they deserve.
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Holy Ghost Preparatory School | Bensalem, Pa | Chief Development Officer
The Chief Development Officer (CDO) identifies, cultivates, solicits and stewards donors to advance the mission of Holy Ghost Preparatory (HGP) School from within all of HGP’s constituencies including the Board of Trustees, committee members, faculty and staff, alumni, current parents, alumni parents, foundations, corporations and other members of the community at large. The incumbent’s focus is on building a culture of philanthropy among all constituencies.
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Horizons at New Canaan Country School | New Canaan, CT | Executive Director
This is an exciting opportunity for a dynamic and visionary individual to lead the flagship Horizons program at New Canaan Country School (“Horizons at NCCS” or “Horizons”) in New Canaan, Connecticut. The Executive Director will partner with the Board to set the strategic vision for Horizons at NCCS’s work, build and lead a high-performing team of five and a summer staff of over 100, and engage with a wide array of stakeholders (students, families, teachers, board members, alumni, donors, and national and local partners).
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Marin Country Day School | Corte Madera, CA | Director of Human Resources
The Director of Human Resources is a strategic leader who designs, scales, and nurtures an exceptional employee experience (EX) across the entire faculty and staff lifecycle. Serving as a trusted partner to school leadership, this individual blends empathy, systems thinking, and data-informed insights to champion an inclusive, high-trust culture where approximately 220 team members thrive.
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Powhatan School | Boyce, VA | Director of Advancement
The Director of Advancement is a collaborative and organized leader who is responsible for leading the advancement strategy, developing and maintaining active relationships with board members, donors, school leadership, faculty and staff. Reporting to the Head of School and serving on the Leadership Team, the Director of Advancement identifies, cultivates, solicits, and stewards major gift donors and develops fundraising strategies.
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Sacred Heart Greenwich | Greenwich, CT | Chief Financial Officer
The Chief Financial Officer (CFO) is a key member of the Senior Leadership Team and serves as the primary financial strategist for Sacred Heart Greenwich. The CFO reports to the President, works closely with the President’s direct reports in academics, enrollment, communications, advancement, and operations, and maintains regular contact with the President, the Chair of the Finance Committee of the Board of Trustees, and the full Board.
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Saint Thomas' Episcopal School | Houston, TX | Preschool Director
Saint Thomas’ Episcopal School seeks a Preschool Director who provides visionary, administrative, and educational leadership for the Early Childhood division (Pre-K and Kindergarten). Reporting directly to the Headmaster, the Director is responsible for cultivating a safe, joyful, and academically enriching environment where young children grow spiritually, intellectually, emotionally, and socially.
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Sayre School | Lexington, KY | Director of Finance and Operations
Sayre School is seeking an experienced, strategic, and collaborative Director of Finance and Operations (DFO) who excels at communicating clearly and efficiently with stakeholders at all levels. The DFO is responsible for managing the school’s financial, operational, and physical resources, directly overseeing finance, annual audits, facilities, campus security, food services, and outsourced operations.
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Springside Chestnut Hill Academy | Philadelphia, PA | Director of Human Resources
The Director of Human Resources provides vision, leadership, planning, and strategic guidance to the HR function. This role ensures a cost-effective HR department while facilitating efficient, compliant operations aligned with the school’s mission and values. The Director serves as a key member of the school’s leadership team and creates and maintains a high-touch, deeply engaging employment experience for all employees.
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St. George's Episcopal School | Milner, GA | Director of Advancement and Communication
The Director of Advancement & Communications serves as a key member of the school’s leadership team, working closely with the Head of School, and is responsible for building a strong culture of philanthropy and supporting long-term institutional sustainability. This role leads advancement strategies around annual giving, donor stewardship, and the Get-Away-Gig auction.
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St. Michael's Catholic Preparatory School | Austin, TX | Director of College and Academic Counseling
St. Michael’s Prep seeks an experienced Director of College and Academic Counseling who is excited to engage in the community and dedicated to the mission of the school. This position reports to the Head of Upper School.
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St. Michael's Catholic Preparatory School | Austin, TX | Director of Student Wellness
SMP is seeking an experienced Director of Student Wellness to join our administrative team. The Director will be the senior administrator responsible for supporting student wellbeing and balance within the Upper School (Grades 9–12).
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St. Michael's Catholic Preparatory School | Austin, Texas | Head of Lower School
St. Michael’s Catholic Preparatory School is entering an exciting period of thoughtful academic and programmatic growth. The next Head of Lower School will join a strong leadership team and help shape the continued development of a Lower School experience that is intellectually engaging, spiritually grounded, developmentally responsive, and deeply attentive to the formation of the whole child.
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The Fay School | Houston, TX | Director of Communications
The Director of Communications is a collaborative, creative, and hands-on member of The Fay School’s Advancement team responsible for executing the School’s communications, marketing, and storytelling. The Director brings the life of Fay to its audiences through timely, engaging, polished, and consistent communications across platforms. The successful candidate is an exceptional doer who thrives in a fast-moving school environment, demonstrates strong attention to detail, and takes projects from idea through execution.
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The Meadowbrook School of Weston | Weston, MA | Director of Development
Reporting to the Chief Advancement Officer (CAO), the Director of Development (DOD) will serve as an integral member of the organization and partner to the CAO, providing innovative and strategic leadership with a commitment to philanthropic engagement and growth to advance Meadowbrook’s mission.
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The Roeper School | Bloomfield Hills, MI | Director of Finance and Operations
The Roeper School seeks an experienced, strategic, and collaborative Director of Finance and Operations (DFO) to provide leadership and oversight of the School’s financial, business, and operational functions. The DFO is responsible for the planning, implementation, management, and control of the School’s financial and business activities while providing leadership for its daily operations.
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The TEAK Fellowship | New York, NY | Chief Financial Officer
TEAK is seeking a strategic, collaborative, and missiondriven financial leader to serve as Chief Financial Officer. The CFO will serve as TEAK’s senior financial leader and a key member of the senior leadership team, responsible for financial strategy, long-term planning, budgeting, forecasting, accounting, audit, compliance, risk management, endowment oversight, and the financial and administrative systems that support TEAK’s mission and sustainability.
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York School | Monterey, CA | Director of Enrollment
The Director of Enrollment 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.
Leadership and/or Non-Teaching Opportunities
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The Director of Transportation is responsible for the safe, efficient, and reliable operation of the School’s transportation program. The Director oversees school bus operations, including driver supervision and scheduling, route design, fleet maintenance and regulatory compliance, and transportation for athletic events, field trips, and other School activities.
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Canterbury School seeks a Head Boys’ Varsity Ice Hockey Coach for immediate employment for the 2026-2027 school year. Candidates must enjoy working with adolescents, possess an exceptional work ethic, and embrace a commitment to teamwork. Strong preference will be given to candidates with a proven record of both playing, coaching, and recruiting experience. In addition to in-season coaching responsibilities, the Head Boys’ Varsity Ice Hockey Coach is responsible for coordinating Fall Hockey, recruiting year-round, and supporting Boys’ Ice Hockey players throughout the school year, including with their college processes. The position includes additional responsibilities, including a primary faculty position and evening coverage.
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The Director of Buildings and Grounds oversees the physical operation of all school facilities, including day-to-day campus use, buildings maintenance and groundskeeping, equipment, furniture, vehicles, and special projects, all with a hands-on approach. The Director of Buildings and Grounds is a detail and systems oriented professional with a demonstrated ability to manage and motivate staff and lead projects in the midst of a vibrant Prek-8th grade campus community.
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Charles River School seeks a thoughtful, organized, and service-oriented Human Resources Manager to support the school’s faculty and staff throughout the employee lifecycle. Reporting to the Director of Finance and the Head of School, the Human Resources Manager will manage day-to-day human resources operations, including recruitment and onboarding, benefits and leave administration, payroll support, employee records, and compliance.
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Columbia Grammar & Preparatory School seeks an Associate Director of College Counseling to play a pivotal role in guiding students and families through every stage of post-secondary planning. This 10-month, high-touch position combines strategic counseling, administrative leadership, and external advocacy.
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Congressional School seeks a dynamic and collaborative Director of Athletics and Physical Education to lead its comprehensive physical education and Middle School inter-scholastic sports programs. The Director leads and works side-by-side with a dedicated team— including PE teachers, athletic coaches, and aquatics personnel—to deliver a meaningful, developmentally appropriate physical fitness experience that integrates Congressional School’s Mission, Vision, and Core Values.
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Epiphany School seeks a strategic, collaborative, and relationship-focused Major Gifts Officer (MGO) to join our team for the life of the Capital Campaign (~3 years). This position will manage, nurture, and enhance relationships with an individual portfolio of 100-125 prospects to improve probability of continued and increased support of Epiphany School. The MGO will build a major gifts program to identify, qualify, steward, and solicit prospects capable of making gifts of $50,000 or more towards the capital campaign. The MGO will collaborate with Development staff to ensure appropriate stewardship of major gifts donors. The position requires most of the time spent visiting with prospects.
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Reporting to the Senior Associate Director of Institutional Advancement, the Major Gifts Officer at Germantown Academy will serve as a primary fundraiser for the office, securing philanthropic support from a variety of targeted groups of constituents. We are seeking candidates for a full-time position to join our community immediately. This is a 12-month position with an excellent array of benefits and a competitive salary.
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As a member of the Health Services Department, the School Nurse is an RN who works to strengthen and facilitate the educational process through improving and protecting the health status of children within the school setting. The major focus of school nursing services is the prevention of illness and disability, and the early detection and correction of health problems for day and boarding adolescent students.
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Kent School is seeking a dynamic and inspirational Head Coach for Girls’ Rowing who is deeply committed to the growth and well-being of our students. The ideal candidate brings a genuine love of the sport, strong technical and strategic rowing knowledge, and successful coaching experience at the high school or collegiate level. This is an opportunity to build on a proud and competitive tradition. With the full support of an engaged administration and school community, the Head Coach will shape a comprehensive girls’ rowing program that emphasizes athletic excellence, teamwork, resilience, and sportsmanship.
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The Assistant Director of Annual Giving and Advancement Operations is an integral member of the Philanthropy team, reporting to the Director of Philanthropy. The Assistant Director shapes and executes fiscal year Annual Fund strategy and plans, with a focus on broad-based appeals.
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PBDA is seeking an experienced and innovative Special Events and Community Relations Manager to lead the strategy and execution of high-impact events that resonate with our mission and elevate the brand presence of Palm Beach Day Academy. In this role, you will leverage your expertise in event planning and management to create memorable experiences that engage our audience and foster meaningful connections, working toward increased support for the School.
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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 an experienced and dedicated School Counselor to join our team.
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This position joins a dynamic Advancement Office team that spearheads all facets of institutional advancement, including fundraising, constituent relations and engagement, events, alumni relations, stewardship, and communications. The Director of Annual Giving is responsible for developing and implementing an effective, comprehensive Annual Giving program that raises $3 million each year. Reporting to the Director of Advancement and partnering with staff, volunteers, and the Board Advancement Committee, the Director of Annual Giving develops and implements strategies and programs to identify, cultivate, solicit, and steward annual gifts from trustees, alumni, parents, grandparents, parents of alumni, and friends, including personal solicitations, direct mail, and electronic communication.
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The Director of Educational Technology provides strategic leadership for technology and artificial intelligence across TMI Episcopal, with a particular focus on advancing teaching, learning, innovation, and digital literacy. Reporting to the Associate Head of School, the Director partners with academic leadership and faculty to develop and implement a forward-looking vision for the effective, responsible, and innovative use of technology and AI within the educational program.
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Trinity Valley School is looking for a builder to shape the future of our lacrosse program. We need a director who sees the long view — someone ready to formalize our developmental pathway and ensure that our athletes’ experiences on the field are as rigorous and meaningful as their experiences in the classroom.
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The Administrative Assistant to the CFOO plays a key role in supporting the operational and financial functions that keep Westover running smoothly. This position provides comprehensive administrative, clerical, and coordination support to the CFOO and the broader Operations Team, ensuring timely follow-up on projects, clear communication across departments, and efficient management of day-to-day logistics.
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Westover School is seeking a detail-oriented and collaborative Staff Accountant to join the Business Office. Reporting to the Controller, the Staff Accountant plays a vital role in supporting the School's financial operations with primary responsibility for general accounting, accounts receivable, student billing, and student financial account management.

