engaging with our partners
to Conduct Comprehensive Leadership Searches
Connelly School of the Holy Child | Head of School Search
The next Head of School at Connelly School of the Holy Child will have the privilege of joining this Catholic, all-girls, college preparatory school in continuing Cornelia Connelly’s transformative vision, creating a faith-based, educational community where each young woman is trusted, cared for, and empowered to discover and develop her unique gifts in service to others.
This is a calling for a leader who sees education as more than academics, who understands that true learning happens in an environment of trust, joy, and reverence for each individual. It is an opportunity for someone who believes, as Cornelia Connelly did, that education should be “one continuous act of love.”
If you are an authentic, visionary leader with the skills to navigate institutional priorities while maintaining focus on the joy and purpose that make Holy Child distinctive—if you are someone who can inspire young women to advocate for themselves and become women of faith, conscience and action—we invite you to explore this extraordinary opportunity.
Application Deadline: January 5, 2026
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.
Applications are now closed.
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.
Applications are now closed.
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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.
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Charles Wright Academy | Chief Advancement Officer
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.
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University Liggett School | Director of Enrollment Management
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.
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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.
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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.
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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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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.
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Trinity School of Midland | Head of Lower School
Beginning in July 2026, the new Head of Lower School will lead this division in providing a nurturing and developmentally appropriate learning environment for students in Kindergarten to Grade 4. With the appointment of a new Head of School in 2018 and a transformational building project on the horizon, Trinity School is in the midst of a new chapter in its growth and development. This is an exciting time in Trinity School’s history for the next Head of Lower School to help shape the School’s vision for the future.
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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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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.
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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.
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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.
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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.
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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.
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Cannon School | Head of Upper School
As a member of the School’s Leadership Team, the Head of Upper School reports directly to the Head of School and partners with other members of the leadership team to bolster and reinforce Cannon School’s culture in alignment with our mission and core values. The Head of Upper School leads all Upper School educators—faculty and staff—in building a growth-oriented educational program. In this primary objective, the Head of Upper School furthers Cannon’s vision, sustainably enhancing the Upper School experience.
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The Hockaday School | Director of Human Resources
The Director of Human Resources is charged with administering day-to-day HR operations as well as formulating a clear and compelling vision for the future of Human Resources in a large school setting. The Director of Human Resources will report to the Chief Financial Officer and will serve on the School’s Leadership Team.
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Columbia Grammar & Preparatory School | Director of Philanthropy
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
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Delaware Valley Friends School | Director of Philanthropy
The Director of Philanthropy leads the school’s fundraising and advancement efforts, fostering a culture of philanthropy to support the school’s mission and strategic priorities. This role oversees all aspects of philanthropy, including annual giving, major gifts, alumni engagement, events, and stewardship. The director works closely with the other development office members, the Head of School, the trustees, and community stakeholders to cultivate meaningful relationships and inspire philanthropy.
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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.
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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.
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York School | Director of Finance
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.
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Palm Beach Day Academy | Assistant Director of Philanthropy for Annual Giving and Alumni Engagement
The Assistant Director of Philanthropy for Annual Giving and Alumni Engagement 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 and alumni participation.
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Mckee Botanical Garden | Director Of Philanthropy
The Director of Philanthropy plays a critical leadership role in advancing McKee Botanical Garden’s mission, with an immediate focus on guiding and executing a major capital campaign. This position is responsible for developing and implementing strategies that drive fundraising success across major gifts, annual support, grants, corporate partnerships, and donor stewardship.
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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.
Leadership Searches
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Oxbridge Academy seeks a customer-service–oriented, detail-driven, flexible, and kind-hearted Assistant Director of Admission to join a dynamic and mission-aligned Admission Team. The Assistant Director, in collaboration with Admission Team, is responsible for the recruitment, selection, admission, and onboarding of new students to the school, and ensures a smooth process from inquiry through enrollment.
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The Woodstock Day School (WDS) is seeking a 7-12th grade PE teacher for a Temporary Leave coverage between January and April (exact dates to be determined). This role also has responsibility for providing administrative support in the coordination of after school Basketball, Tennis and Golf.
Ideal candidates embrace a range of pedagogical approaches, are excited about teaching in a progressive community and have demonstrated a commitment to addressing issues of diversity, equity, and inclusion within and outside the classroom.
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NCS seeks a strategic, collaborative, and systems-minded Director of Development Operations to play a pivotal role in shaping the future of philanthropy for women’s education.
This is a rare leadership opportunity for a development professional who is passionate about operational excellence and who believes deeply in expanding opportunities for girls and young women.
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The Director of Leadership Giving is a senior advancement professional responsible for cultivating and securing transformational gifts that support Wakefield School’s strategic priorities, including the multi-phase Campus Master Plan and forthcoming capital campaign. With primary responsibility for principal gifts, the Director builds and sustains high-impact relationships with the school’s most generous and engaged supporters.
Reporting to the Head of School, the Director works in close partnership with the Board of Trustees, the Advancement Team, and key volunteer leaders. This leader drives the strategy and execution behind the school’s most significant philanthropic opportunities.
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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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The Brand Strategist & Senior Director of Marketing and Communications leads the development and implementation of a unified brand and communications strategy that elevates the school’s visibility, enhances its reputation, and advances institutional priorities across admissions, advancement, and community engagement.
This position ensures that the school’s story, mission, and values are authentically represented across all platforms and materials. The Senior Director will collaborate closely with creative agencies, internal partners, and key departments to manage marketing campaigns, design strategy, and the rollout of new brand assets. The Senior Director will report to the Head of School.
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The Frederick Gunn School, a co-educational boarding and day school serving students in grades 9-12 and post-graduate, seeks a Chief People Officer (CPO) to join its Senior Leadership Team. The CPO will lead all aspects of the school’s people strategy and human resources function, ensuring that faculty and staff thrive in a culture rooted in trust, growth, and inclusion.
As a strategic partner to the Head of School and senior leaders, the CPO will oversee recruitment, employee relations, compensation and benefits, compliance, and organizational development. This leader will also drive initiatives in leadership development, faculty and staff growth, and the design of equitable systems that align with the school’s mission and values.
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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.
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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.
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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.
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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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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.
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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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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.
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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 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.
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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.
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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.
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The Staff Accountant/Student Accounts Manager reports to the Chief Financial Officer and is an integral part of the Business Office team. The SA/SAM is responsible for management of Student Accounts in addition to other responsibilities as a Staff Accountant.
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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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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.
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The Director of Scholarship Giving is a front-line fundraiser who is responsible for generating annual scholarship support from individuals and corporations utilizing Pennsylvania’s scholarship tax credit program. This role will lead efforts to secure more than $2M annually in scholarship support while developing a growth strategy to meet our growing school community’s needs. The Director is a key collaborator in St. James’ fast-paced, eight-person Advancement Team which collectively raises more than $6M annually while preparing to launch an eight-figure capital campaign to support our ambitious growth projected over the next several years.
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St. Stephen’s and St. Agnes School (SSSAS), a college-preparatory Episcopal school in Alexandria, Virginia, seeks a Certified Athletic Trainer (AT) to join our dynamic athletics department and sports medicine program. The ideal candidate is a skilled, compassionate professional dedicated to the health and well-being of student-athletes and committed to collaboration within a caring school community. The Athletic Trainer will work closely with another full-time AT, the Director of Health Services, and the Athletics staff to deliver exceptional medical care and injury prevention for our Saints athletic program.
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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.
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The basic function of this position is to support students in their social, emotional, and psychological development throughout their high school years. The Counselor provides emotional, behavioral, personal, and crisis counseling on a daily basis. The Counselor coordinates, consults, and collaborates with faculty, parents, administrators, and outsideresources to assist students in managing or remediating issues that are impeding them from leading emotionally and psychologically balanced lives and assisting them in taking full advantage of the educational and support opportunities at TMI. The Counselor initiates and participates in the development of programs that address personal development and/or school climate concerns.
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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.
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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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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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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.
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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. 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.
Current Faculty Searches
MID-ATLANTIC
The Boys' Latin School of Maryland | Upper School STEM Teacher and Residential Life Fellow
Delaware Valley Friends School | Upper School English Teacher
St. Stephen's and St. Agnes School | Upper School History Teacher
Perelman Jewish Day School | Elementary Teacher - Upper Elementary
Hilton Head Preparatory School | Upper School Mathematics Teacher