engaging with our partners
to Conduct Comprehensive Leadership Searches
University Liggett School | Head of School Search
Stepping into the role of Head of School at University Liggett School means leading a nationally respected institution with nearly 150 years of educational excellence and a community deeply committed to its future. This is not a mandate for sweeping change; it is an invitation to guide one of the Midwest’s most respected independent schools and help shape its next era of strength and innovation.
Formed through the merger of four predecessor institutions, University Liggett School stands as a distinguished testament to enduring excellence and has become a nationally recognized PreK-12 college preparatory school nestled in the heart of Grosse Pointe Woods, Michigan. Here, tradition and innovation intersect, preparing students to thrive in an ever-changing world.
University Liggett School seeks a leader who embodies both the heart of an educator and the strategic acumen of an executive: someone who finds profound joy in the daily life of students and teachers while bringing the vision and financial discipline to elevate an already exceptional institution to new heights of excellence and impact.
Telluride Mountain School | Head of School Search
Telluride Mountain School (TMS) in Telluride, Colorado seeks a new head of school to begin in the 2026-27 school year and has partnered with DovetailED to lead the process. Preliminary applications are now being accepted, with the full opportunity statement set to be released in mid-October. To learn more about TMS, click here.
If you'd like to submit a preliminary application package, please send your cover letter and resume to Zack Lehman at zack@dovetailedsourcing.com and Lynda Hamilton-Kirk at lynda@dovetailedsourcing.com. Applicants will have the chance to update their materials once the comprehensive position statement becomes available.
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The St. Paul's School | Lower School Head
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.
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Baker Demonstration School | Director of Admissions
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.
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Cheshire Academy | Dean of Enrollment Management
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.
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Milton Hershey School | Director of Agricultural and Environmental Education
MHS is seeking a Director of Agricultural & Environmental Education (AEE) to lead the school’s exceptional Agricultural & Environmental Education Program. This program offers hands-on learning experiences for all MHS students in agriculture, horticulture, and environmental sciences, and supporting students through career tracks, clubs, and work experiences.
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Khan Lab School | Senior Director of Finance and Administration
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.
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Oak Hill School | Director of Enrollment Management
Oak Hill School is seeking a Director of Enrollment Management to lead student recruitment, retention, and admissions at Oak Hill School. The Director plays a key role in welcoming families, building strong relationships, and ensuring a positive and seamless experience from inquiry through enrollment. This position requires a collaborative leader who enjoys connecting with people, building trust, and promoting the value of an Oak Hill education.
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Shady Side Academy | Major Gifts Officer
Shady Side Academy is seeking a Major Gifts Officer looking to contribute to a growing Alumni & Development Team.
The Major Gifts Officer plays a critical role in advancing our school’s mission by building and managing relationships with high-capacity donors. This position is responsible for identifying, cultivating, soliciting, and stewarding major gift prospects and donors to secure significant philanthropic support for the school’s strategic priorities and initiatives.
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Castilleja School | Director of Human Resources
Castilleja School is seeking an experienced Director of Human Resources. A successful Director of Human Resources at Castilleja will have a high level of cultural responsiveness and will be eager to support and endorse the school’s commitment to these ideals. The Director of Human Resources will have a deep understanding of faculty and staff culture - what motivates them and what they need to be successful in their roles. The Director will be an exceptional communicator, inclusive leader, and a strategic thinker.
The Director of Human Resources supervises the Payroll and Benefits Manager and is a member of the school’s Finance & Operations Team. This is a full-time, onsite, exempt position reporting to the Associate Head of School for Finance and Operations.
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The Roper School | Director of the Lower School
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.
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Church Farm School | Director of Development
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.
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York School | Director of Philanthropy
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.
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Saint Mary's Hall | Chief Financial Officer
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.
Leadership Searches
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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.
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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.
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A member of the Advancement team, the Special Events Manager is responsible for the programmatic and administrative support of all aspects of adult-facing events related to the Advancement Office and the School. The Events Manager will serve as the lead coordinator for high quality, high-touch, on-campus, off-campus, and virtual event planning and coordination working closely with The Head of School, the Assistant Head for Advancement and other campus leaders in addition to the Advancement Office. The position is responsible for managing venue logistics, communication, budget details, and collaborating with leadership volunteers and colleagues from across campus to ensure successful completion of all events. The position also supports adult-facing campus-wide events led by other departments, providing guidance and resources as needed.
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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.
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Hudson Way is looking to hire an Enrollment Manager or Director (based on the experience of candidate). This position is responsible for the new and continuing enrollment of students at the NY campus for day school, after school, summer camp and enrichment programs. This position manages the financial aid for day school working with the CAO, and manages the after school program manager to ensure that profit and loss targets are met. This position also directs the marketing manager in specific items needed to support the campus events.
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King School seeks a dynamic Capital Campaign Director & Major Gifts Officer to drive the success of the All In Campaign and manage major donor relationships and solicitations. Working under the strategic direction of the Director of Development, this individual will oversee campaign strategy and execution, actively cultivate and solicit major gifts, and collaborate with trustees, the Head of School’s office, school leadership, and the development team to advance fundraising goals. This role also serves as a key thought partner to the Director of Development, contributing to overall fundraising strategy and donor engagement initiatives.
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Middlesex School seeks a Leadership Giving Officer to build a strong base of individual donors to support the ambitious and strategic growth of the organization. The LGO will be responsible for identifying, cultivating, soliciting, and stewarding individual prospects with an estimated capacity to support Middlesex with gifts of $100,000 or more. Key to success in this role will be identifying and building relationships with new prospects as well as strengthening relationships with existing donors to maximize philanthropic support. In addition to soliciting annual major gifts, the LGO will support efforts to solicit transformational campaign gifts, work with reunion classes on leadership gifts, and engage in efforts related to both Alumni and Parent giving.
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Reporting directly to the Director of Marketing & Communications, the Assistant will serve as a trusted partner, providing high-level administrative, organizational, and project support in a fast-paced environment. This role requires exceptional attention to detail, advanced proofreading skills, sound judgment, and the ability to manage competing priorities under tight deadlines. The ideal candidate is a seasoned professional, has a polished communication style, and a proven track record of supporting senior leaders.
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The Admissions Data Analyst plays a key role on the enrollment team as it supports the mission and overall strategic objectives of OES. The admissions staff works to fully enroll students while maintaining class compositions that demonstrate cultural, geographic, economic, gender, religious, racial and ethnic diversity. This individual manages the admissions database and is the data analyst responsible for interpreting and designing crucial statistical information for presentation to stakeholders. This position also supports other school divisions and programs periodically throughout the year in project specific opportunities for data analysis. Success in this role requires expertise in data management, highly developed powers of analysis, talent in information design, sensitivity in dealing with confidential information, and excellent communication skills. The admissions data analyst works closely with the assistant head of school to develop and implement strategies for successfully attaining enrollment goals. The successful associate will be flexible and conscientious, possess excellent cross-cultural communication skills, and continually keep equity and justice at the forefront of their work.
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The admissions associate for Lower School (LS) plays a key role on the enrollment team as it supports the mission and overall strategic objectives of OES. The admissions staff works to fully enroll students while maintaining class compositions that demonstrate cultural, geographic, economic, gender, religious, racial and ethnic diversity. This individual demonstrates a thorough understanding of the recruitment and enrollment process by participating in all aspects of the admissions process, and through building strong, positive relationships within the OES community, with applicants, and their families. The admissions associate for Lower School works closely with the Assistant Head of School for Strategic Enrollment to develop and implement strategies for successfully attaining enrollment goals. The successful associate will be flexible and conscientious, possess excellent cross-cultural communication skills, and continually keep equity and justice issues at the forefront of their work.
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Saint Mary’s Hall seeks a skilled and dynamic academic support specialist. Working with the Assistant Head of School for Academics, Division Head, counseling staff and athletic trainer as appropriate, this individual will assess and implement an appropriate academic support plan for students with diverse learning styles, documented accommodations, and whose medical conditions require academic support (such as students recovering from concussions).This individual will also support families that may want to learn more about potential diagnostic testing and will facilitate accommodation documentation and implementation with College Board and ACT assessments.
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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 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.
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The Advancement Office’s mission is to engage constituents in the life of Westover School through engagement and philanthropy. The Assistant Director of Advancement plays a critical role by providing both strategic leadership and daily management of engagement initiatives within the Office of Advancement. This role fosters meaningful connections between Westover and its alumnae, families, and friends, oversees key volunteer programs, and develops initiatives that enhance constituent involvement.
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The Operations Coordinator plays a central role in supporting the day-to-day functioning of Westover’s campus operations. Reporting to the Chief Finance and Operations Officer (CFOO), the Coordinator provides essential administrative and logistical support across key operational departments, including facilities, food service, housekeeping, transportation, security, the school store, and the mailroom.
The position requires strong organizational and communication skills and a service-oriented mindset. The Coordinator will also serve as a licensed school driver as needed to support student transportation needs.
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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.
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The Winchendon School seeks a Head Boys Varsity Lacrosse Coach and Recruiter to lead our growing program. This is an opportunity for a motivated individual to build a competitive and values-driven lacrosse program while playing a key role in student-athlete recruitment and college placement.
This position is designed to be full-time, ideally paired with significant responsibilities in the School’s college counseling, admissions, athletics administration, or student life offices. The right candidate will be collaborative, student-centered, and eager to contribute to the broader life of a boarding/day school community. We will also consider part-time applicants who bring deep coaching experience, strong recruiting networks, and availability to be present on campus regularly.
Current Faculty Searches
SOUTH / SOUTHEAST