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.

Learn more

Telluride Mountain School | Head of School Search

Telluride Mountain School stands at an important and promising juncture. This school has an exceptional legacy, a passionate community, and tremendous potential. The entire TMS community is deeply invested in the school’s future and ready to support a leader who can articulate the school’s value, galvanize stakeholders around a shared vision, and guide the institution toward sustainable growth while honoring its progressive roots.

The next Head of School will find a community eager for partnership, optimistic about the future, and committed to preserving what makes TMS special. At the same time, the next Head of will guide the school’s continued evolution by championing needed changes and engaging the community throughout the process. This is not a school requiring turnaround; it is a school seeking decisive, transparent leadership to navigate enrollment challenges, strengthen its market presence, and build on its considerable strengths.

The Head of School at TMS serves as the school’s chief storyteller, ambassador, and educational leader, working in partnership with the Board of Trustees to carry out the school’s mission and articulate its vision to all constituencies. The Head oversees the shaping of the school’s academic program and the quality of life in the school community, establishes an effective and collaborative leadership approach, and ensures that every element of school life reflects the principles of equity, justice, and human dignity.

Learn more

Connelly School of the Holy Child | Head of School Search

Connelly School of the Holy Child 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-November.

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.

  • Foxcroft School | Assistant Head of School

    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 Emery/Weiner School | Assistant Head of School

    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 | 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.

  • Khan Lab School | Lower School Director

    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.

  • 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.

  • 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.

  • Wyoming Seminary | Head of the Upper School

    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.

  • Gulliver Preparatory School | Upper School Principal

    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 Upper School Principal will work closely with the Head of School, fellow administrators, department chairs, and faculty to materialize the two central pillars of the recently approved strategic plan: The first is Next Level Teaching and Learning, which reflects Gulliver’s commitment to being a nationally-recognized school for personalized achievement and academic excellence. The second is Thriving Students, which focuses on student health, wellness, and nurturing a community of belonging.

  • The Roeper 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.

  • King's Academy | Deputy Head of School

    King’s Academy—a leading coeducational boarding and day school serving grades 7–12 in Madaba, Jordan— seeks a Deputy Head of School to begin in July 2026. This is a pivotal senior leadership opportunity to partner closely with Head of School Penny Townsend in advancing King’s mission and strategic priorities while overseeing the daily operations of a vibrant, diverse international school community. Founded in 2007 by His Majesty King Abdullah II, and modeled on the best traditions of American independent and international schools, King’s Academy blends rigorous academics, holistic student development, and a profound commitment to global citizenship. The Deputy Head of School will help sustain the school’s exceptional programmatic breadth while strengthening the systems and culture that support its next chapter of excellence. This role offers an extraordinary opportunity to contribute to an institution of national and regional significance and to play a key leadership role in shaping its future.

  • Saint Thomas' Episcopal School | Head of Lower School

    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 Winchendon School | Director of Admissions or Director of Enrollment Management

    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.

  • Dublin School | Director of Advancement

    Dublin School has engaged DovetailED to facilitate the search for a new Director of Advancement. This person will be a member of a veteran, nine-person Leadership Team, reporting to the Head of School, and will follow the twenty-five year tenure of Erika Rogers. The nine-person Leadership Team of Dublin’s senior administrators meets weekly. This group includes the Head of School, the Executive Assistant to the Head, Director of Enrollment Management, the Associate Head for Academics, the Director of Advancement, the Dean of Faculty, the Athletic Director, the Dean of Students and Belonging, and the Director of Finance and Operations.

    The new director will be someone who deeply appreciates the mission of this small, intimate school in a stunning location and will enthusiastically promote all Dublin has to offer in broad and creative ways.

  • Millbrook School | Director of Annual Giving & Engagement

    Annual giving has always been the centerpiece of philanthropy at the Millbrook; it is a central pillar of every capital campaign, including the current For ALL campaign, with an AF target of $20 million as part of the overall $150M million effort.

    The Director of Annual Giving and Engagement reports directly to the Director of Advancement. This position is charged with managing Millbrook’s Annual Fund program that will help increase participation and fundraising dollars for the school. This role will lead the Annual Fund (digital and print marketing, leadership of Annual Fund giving, and the Sixth Form Gift initiative) as we look to increase overall fundraising to $3M+ each year.

  • The Meadowbrook School of Weston | Head of Lower School

    The Meadowbrook School of Weston, a junior kindergarten through 8th grade school located seven miles west of Boston, is seeking a visionary and dynamic Head of Lower School to join our community starting July 2026.

    This is a full-time, year-round, exempt administrative position. Reporting directly to the Assistant Head of School, Academics and Inclusion, the Head of Lower School is an integral member of the school’s senior leadership team. Meadowbrook is a fast-paced, dynamic environment where no two days are the same, especially in the Lower School (JK-5). The Head of Lower School serves as the educational and administrative leader of the division, with comprehensive responsibility for the students, faculty, curriculum, and parent relations.

  • 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.

  • 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.

  • 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.

  • Castilleja School | Director of Enrollment Management

    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.

  • 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.

  • The John Cooper School | Director of Development

    The Director of Development will provide strategic oversight and direction for the School’s annual fundraising programs, including the Cooper Annual Fund and Advancement Events such as the Gala, Signatures Author Series, and Golf Outing. This role also oversees the School’s Alumni Engagement efforts, which are vital to building a strong and sustainable culture of philanthropy and lifelong connection to Cooper. Reporting to the Chief Advancement Officer, the Director of Development plays a key role in increasing philanthropic revenue, enhancing the donor experience, expanding our engagement programs, and building a pipeline of future major donors.

 Leadership Searches

  • The Annual Giving Coordinator/Manager is responsible for planning and executing a comprehensive annual giving program; creating, organizing and implementing all activities related to The Roeper Annual Fund and donor-centered communications related to fundraising initiatives. As the cornerstone of philanthropy at The Roeper School, the Annual Fund plays a critical role in advancing the school’s mission and cultivating a culture of generosity. The Annual Giving Manager/Coordinator will inherit a growing program and will work in close collaboration with the Development Team. This position holds opportunities for growth and reports to the Director of Development.

    Learn More

  • The Upper School Math Department Chair at Gulliver Preparatory School provides leadership and direction for the mathematics program, ensuring it upholds the school’s mission and the highest standards of teaching and learning. This role supports and mentors faculty, promotes innovative and engaging instruction, and fosters a collaborative culture focused on student growth and well-being. Working closely with colleagues and administrators, the Chair advances interdisciplinary learning, integrates technology effectively, and helps maintain a dynamic, student-centered academic environment.

    Learn More

  • The Benjamin School is seeking a Director of Facilities to join our team. The Director of Facilities is responsible for the strategic oversight, management, and daily operations of all physical facilities, safety, and security functions across the Benjamin School’s two campuses located in North Palm Beach, FL and Palm Beach Gardens, FL. This includes maintenance, custodial services, groundskeeping, construction, physical plant operations, safety, and campus security. The Director ensures that the school’s buildings, grounds, and physical infrastructure support a safe, healthy, and inspiring learning environment. The Director of Facilities will also be a key member of our Safety and Security Team.

    Learn More

  • Trinity Valley School seeks a full-time (12-month) team member to serve in the dual role of Assistant Director of Admissions and Financial Aid and Head Boys’ Varsity Lacrosse Coach. This position is a critical link between the Admissions and Athletics departments and reports jointly to the Director of Admissions and Enrollment Management and the Director of Athletics.

    Learn More

  • 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.

    Learn More

  • The Lower School Counselor provides counseling support for students and is an integral part of the LS culture. This position works closely with the LS Learning Support Specialist to meet student needs. To that end, the counselor collaborates with the LS Student Support Team, leadership, and faculty/staff, and partners with families. The counselor develops, leads, coordinates, and promotes initiatives and projects that benefit the LS and the larger OES community. A member of the all-school Student Support Team, this position is one of the two links that connect student support across the Upper, Middle, and Lower Schools. The LS counselor is essential in fulfilling the program’s mission.

    Learn More

  • 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.

    Learn More

  • Beside Bateman’s Pond stands the Warburg Library, a magnificent space filled with light, life, and potential. Middlesex School is seeking a Director of the Warburg  Library who will imagine what a 21st-century library can be: not only a repository of  knowledge, but a hub of intellectual curiosity, connection, and discovery. 

    The next Director will bring vision and expertise to reimagine this central space as a  living classroom. Working closely with the Associate Head of School, Academic  Department Heads, and colleagues across campus, the Director will guide the library  into its next chapter, blending tradition and innovation to serve the next generation of Middlesex students.

    Learn More

  • 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.

    Learn More

  • The Director of Philanthropy provides visionary leadership in securing transformational gifts that strengthen the school’s financial foundation and advance its strategic priorities. Focused exclusively on principal gifts, the Director builds and sustains high-impact relationships with the school’s most generous and engaged supporters. Working in close partnership with the Head of School, Director of Institutional Advancement and Board of Trustees, this leader drives the strategy and execution behind the school’s most significant philanthropic opportunities.

    Learn More

  • The Newman School invites dynamic professionals to apply for the full-time role of Senior Associate Director of Admissions, a key position contributing to shaping our vibrant learning community. Reporting directly to the Director of Enrollment, the Senior Associate Director will oversee one line of enrollment, Middle School (Grades 7–8) or High School (Grades 9–12 & PG), and play a pivotal part in advancing our enrollment strategy.

    As a leader within the admissions team, you will champion a personalized, mission-driven experience for every prospective family. You will be empowered to ensure each grade within your division reaches its enrollment targets by leveraging data-driven insights, strategic planning, and a spirit of collaboration. Your work will foster strong relationships with students, parents, and colleagues, promoting an inclusive environment defined by Newman’s “heart speaks to heart” philosophy.

    Learn More

  • 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.

    The CAO serves as a key strategic partner to the Head of School in shaping and sustaining the school’s financial health and reputation. This role is responsible for driving tuition revenue through effective enrollment management, building philanthropic support through annual giving and capital campaigns, and enhancing the school’s visibility and connection with its community through strategic marketing and communications.

    The CAO leads a talented team that includes directors and staff in development, enrollment, marketing, and communications, promoting collaboration and alignment across these functions to ensure a cohesive approach to mission advancement and long-term sustainability.

    Learn More

  • The Associate Director of Advancement reports to and collaborates with the Chief Advancement Officer to manage and implement the operating program and budget of the fundraising and constituent relations department to advance the mission of Friends School of Baltimore. The Associate Director provides innovative leadership, managerial oversight, and strategic direction to the Office of Advancement through project coordination, staff supervision and performance management, strategic planning and implementation, and budget management, upholding and ensuring department-wide collaboration.

    Learn More

  • 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.

    Learn More

  • Wooster School seeks a candidate with a can-do disposition, who is positive and flexible in the myriad ways a small independent school necessitates. A thorough understanding of selective college admissions processes and trends as they relate to financial aid, the visual and performing arts, and athletics, is a must, and experience as a classroom teacher is a bonus, but not a requirement. We also value those who are curious about how the changing landscape of higher education may change our responsibilities as 5-12 educators in the future. Candidates must be willing to be flexible with evening commitments as needed. A Bachelor’s degree is required, and a Master’s degree is preferred. 

    Learn More

  • 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.

    Learn More

  • 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.

    Learn More

  • Reporting to the Executive Director of Development, the Director of Donor Relations and Stewardship is responsible for leading the effective education, cultivation, acknowledgement, recognition, and stewardship of St. Albans School’s annual, major, planned giving and Campaign donors and prospective donors. This is a full-time, twelve-month position.

    Learn More

  • Cushing Academy seeks a dynamic and experienced Leadership Gift Officer to join our advancement team and play a pivotal role in securing leadership gifts that will advance the Academy’s strategic priorities. This position is responsible for identifying, cultivating, soliciting, and stewarding leadership-level donors (annual, major and planned giving) while building meaningful relationships that support Cushing’s mission of preparing students for success in college and life.

    Learn More

  • The Emery/Weiner School (EWS) seeks an Associate Director of Development to support the mission of the School by developing and administering fundraising campaigns and events, building strong relationships with donors and prospective donors, and cultivating a strong base of philanthropic support in our community.

    Learn More

  • 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.

    Learn More

  • 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.

    Learn More

  • 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. The ideal candidate is highly organized, detail-oriented, and proactive—someone who enjoys managing a wide variety of administrative tasks, coordinating multi-step operational projects, and serving as a reliable point of coordination for the CFOO and campus operations.

    Learn More

  • 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. 

    Learn More

  • 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.

    Learn More

  • 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.

    Learn More

  • The Meadowbrook School of Weston, a junior kindergarten through 8th grade school located in Weston, MA, seven miles west of Boston, is seeking a Senior Facilities Manager to join our community. This is a full-time, year-round, exempt position.

    Reporting to the Director of Facilities, the Senior Facilities Manager is an integral member of the facilities team. In addition to routine maintenance activities, you will act as the main point of contact for the rest of the team, vendors, contractors, and supervise and manage two full-time Facilities Technicians. This role requires a significant exercise of sound judgement and discretion in managing day-to-day operations and staff. At times when the Director of Facilities is absent, you will lead the department.

    Learn More

  • The Assistant Athletics Director will assist the Director of Athletics in supervising the athletic programs, related transportation and logistics, and assisting with the year- round auxiliary rentals and usage of campus facilities. The Assistant AD will also teach a section of Health class, and coach 1-2 seasons. This is an exciting opportunity for an early-career professional seeking leadership growth, and responsibilities may vary based upon the successful candidate’s experience and areas of interest.

    Learn More

Current Faculty Searches