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. Preliminary applications are now being accepted, and the full opportunity statement is scheduled for release in early October.
If you'd like to submit an early application package, please send your cover letter and resume to Zack Lehman at zack@dovetailedsourcing.com and Lynda Hamilton-Kirk at lynda@dovetailedsourcing.com. DovetailED will guide applicants through the subsequent steps of the process.
Executive Opportunities
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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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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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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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Friends Select School | Philadelphia, PA | Executive Assistant and Project Manager for the Head of School
The Executive Assistant and Project Manager to the Head of School is a central partner in the effective operation of the Head’s Office and the advancement of schoolwide priorities. The position provides high-level executive and administrative support to the Head of School, serves as the primary administrative liaison between the Head of School and the Board of Trustees, and coordinates projects and initiatives that require collaboration across the school.
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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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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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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 | Communications and Marketing Manager
The Communications & Marketing Manager leads York School’s strategic communications, marketing, branding, storytelling, public relations, digital engagement, constituent acquisition, engagement, and conversion efforts in support of the school’s mission, strategic priorities, enrollment objectives, philanthropic initiatives, and institutional reputation. This role is responsible for leveraging communications and marketing strategies to drive measurable enrollment, engagement, and philanthropic outcomes across the constituent lifecycle.
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Westover School | Middlebury, CT | Administrative Assistant to the Chief Financial and Operations Officer
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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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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Almaden Country Day School seeks experienced educational leaders to support and advance its nationally recognized The Learning Center (TLC), a specialized program serving students with dyslexia and other language-based learning differences. These leadership roles call for compassionate administrators with Orton-Gillingham certification and experience in educational leadership and instructional coaching. With its recent Orton-Gillingham Academy accreditation, TLC is poised for continued growth and innovation while remaining deeply integrated within the broader ACDS community.
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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 Senior Accountant position is an essential part of Cate’s financial management team. The position involves a high degree of interaction and communication with internal departments, faculty, parents, and vendors. The position includes the ability to organize and streamline accounting processes and consider workflow changes to increase efficiency and maintain internal controls and holds primary responsibility for all accounts receivables, includes collaborative work with our families, advancement and admission departments, other colleagues and vendors. A high degree of confidentiality and professionalism is required. This position works most closely collectively and collaboratively with the Head of Finance and Operations, Controller, Payroll and Benefits Specialist, Accounts Payable, Director of Business Affairs and other office personnel.
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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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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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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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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. Additionally, the Director may serve as a Professional School Nurse, providing direct care as well as being part of the evening and weekend on-call rotations.
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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 Director of Annual Giving & Communications serves as the primary architect of the school’s philanthropic voice and the driver of the $2,000,000 OES Annual Fund. Beyond meeting financial targets, this role is a strategic thought partner to the CAO and the Major Gift team.
This position serves as the hub and coordinator for department communication, ensuring that every piece of communication—from alumni newsletters to campaign proposals—is cohesive, brand-aligned, and strategically designed to support “comprehensive” giving. This role is essential in preparing the groundwork for double and triple asks, ensuring that donors are moved seamlessly through the pipeline from annual support to major and planned gifts.
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The Director of Summer Programs provides visionary, strategic, operational, and pedagogical leadership for all aspects of Oregon Episcopal School’s summer programming. The Director will transform OES summers into a nationally recognized extension of the school’s mission—advancing inquiry, leadership, belonging, innovation, stewardship, and community while strengthening enrollment, partnerships, and long-term institutional sustainability
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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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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. The Director will lead the college and academic advising program and support students throughout the entire college admission and academic counseling process beginning in the spring of 8th grade, using a cohortlooping model in which each counselor accompanies a group of students from 9th grade through graduation. The Director will work closely with the Head of Upper School and Academic Deans to help create and implement a forward-thinking approach to academic and college advising.
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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). This is a role for every student, not only those navigating a specific challenge: the Director will champion a healthy rhythm of academic, spiritual, social, and personal life, helping students build the habits and perspective to thrive under the ordinary pressures of Upper School — workload, sleep, activities, relationships, and expectations — while also ensuring thoughtful support is in place for students who need more.
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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 Ursuline School seeks a strategic and relationship-driven Manager of Annual Giving to join its Advancement team. Reporting to the Chief Advancement Officer, this individual will lead the planning, execution, and growth of the school’s Annual Fund and parent giving initiatives. The ideal candidate is a collaborative and results-oriented professional who can effectively engage alumnae, parents, past parents, faculty, staff, and friends in support of the school’s mission through thoughtful cultivation, solicitation, and stewardship.
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The Walker School is seeking a dynamic, relationship-driven fundraising professional to serve as its next Assistant Director of Development. This is an exciting opportunity for a strategic and mission-aligned leader to help shape a culture of philanthropy within a vibrant independent school community. If you are energized by building meaningful relationships, advancing mission-driven work, and making a lasting impact through philanthropy, this role offers the opportunity to do just that.
As a key partner to the Assistant Head of School for Advancement, the Assistant Director of Development will play a central role in designing and executing a comprehensive development strategy. This position will help grow philanthropic support while strengthening engagement across parents, alumni, and friends of the school. This is a highly visible role for a professional who thrives at the intersection of strategy and relationship-building and who is passionate about independent school education and nonprofit impact.
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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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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.