engaging with our partners
to Conduct Comprehensive Leadership Searches
University Liggett School | Head of School Search
University Liggett School (ULS) initiated its Head of School search in August 2025, partnering with DovetailED to lead the process. Early interest applications are now being accepted, with the full opportunity set to be released in early October. To learn more about ULS, click here.
If you'd like to submit an early application package, please send your cover letter and resume to Zack Lehman at zack@dovetailedsourcing.com and Lynda Hamilton-Kirk at lynda@dovetailedsourcing.com. Applicants will have the chance to update their materials once the comprehensive position statement becomes available.
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Trinity Valley School | Director of Human Resources
Trinity Valley School seeks a Director of Human Resources who believes in the power of people to transform a school—one who wants to make a lasting impact by building a thriving, mission-driven community.
In this vital leadership role, you will do more than manage payroll, policies, and compliance—you will lead the development of a people-first strategy that aligns with the TVS mission and values. You will help ensure that all employees are valued and enabled for success.
With your vision, empathy, and expertise, you will help shape and inspire a culture that brings out the best in our staff—so our students get the best from each of us.
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The Chestnut Hill School | Director of Enrollment Management & Financial Aid
The Chestnut Hill School, founded in 1860 and located in Chestnut Hill, Massachusetts, is an independent, all-gender school for children ages 3 through grade 6. At the Chestnut Hill School, we believe childhood optimism and enduring curiosity can transform the world.
The Director of Enrollment Management & Financial Aid is responsible for all activities in the Admission Office from the initial inquiry through matriculation and retention. A member of the Senior Administrative Team, the Director of Enrollment Management & Financial Aid represents the school and its mission to prospective families and the community, and works closely with the Head of School to implement a comprehensive strategy to enroll and retain a diverse student body.
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University Liggett School | Director of Human Resources
The Director of Human Resources leads the school’s efforts to attract, develop, support, and retain exceptional faculty and staff across all divisions. This leader manages the full employee lifecycle—from recruitment and onboarding through development and performance management to offboarding—with a focus on promoting a workplace culture that reflects the school’s values of Community, Integrity, Respect, Excellence, and Empathy. The Director serves as a key partner to the Head of School, Senior Leadership Team, and Business Office in supporting a high-performing and mission-aligned workforce. The ideal candidate combines deep HR expertise with a warm, approachable leadership style grounded in empathy and discretion.
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St. Andrew's School (DE) | Director of Communications
St. Andrew’s School seeks a Director of Communications. The ideal candidate will be a team leader who cultivates a nurturing and productive environment while valuing authenticity and substance over style. They will bring a well-read and deeply knowledgeable perspective to their work, along with exceptional storytelling and writing skills and the ability to create compelling, original content. With proven experience in crisis communications, this individual will excel in navigating challenges with confidence and clarity.
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Middlesex School | Assistant Director of Alumni Giving and Engagement
Middlesex School seeks an Assistant Director of Alumni Giving & Engagement to cultivate relationships with young alumni and build a strong pipeline of annual donors in support of the school’s mission. Reporting to the Director of Development, the Assistant Director will work collaboratively with the Annual Giving team to secure support for the Middlesex Annual Fund from graduates of the last 15 years. This role focuses on identifying, cultivating, soliciting, and stewarding these donors, with an emphasis on recent graduates.
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Saint Mary's Hall | Chief Financial and Operating Officer
The Chief Financial and Operating Officer (CFOO) is a key member of the senior leadership team, responsible for overseeing the financial health and operational management of the school. The CFOO provides strategic 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, Finance Committee, and other key stakeholders.
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The Roeper School | Director of Enrollment Management and Financial Aid
Founded in 1941, The Roeper School, serving preschool through 12th grade, is the nation’s oldest independent school for gifted learners. We empower gifted students to become thoughtful, compassionate citizens through a progressive, student-centered approach.
The Director of Enrollment Management reports to the Head of School and is a member of the Leadership Team. The Director is responsible for recruitment and outreach strategy, the admission process from inquiry through enrollment, and retention management including the reenrollment process. They manage the Enrollment Management team and collaborate closely with the Communications and Marketing team, Development team, Head of School, and other members of the Leadership Team to ensure that the school meets both short-term and long-term enrollment goals with mission aligned students who will benefit from and contribute to the Roeper community.
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York School | Director of Advancement
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.
The Director of Advancement reports directly to the Head of School and provides staff support to the Board of Trustees’ Philanthropy Committee, Enrollment and Marketing Committee, and Committee on Trustees. This position works closely with the Head and trustees and oversees the philanthropy functions of the school with specific responsibility for capital and endowment fund raising, major gifts, planned gifts, corporate and foundation relations, annual giving, special events, alumni relations, and communications. The Director of Advancement also supervises the work of the Enrollment Department, ensuring that the school is able to enroll and retain mission-appropriate students and that the school is positively perceived by prospective families and by the community in general.
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The Boys’ Latin School of Maryland | Director of Development
The Boys’ Latin School of Maryland, the Mid-Atlantic’s oldest K – 12 school for boys, with a residential life program from students in grades 9 – 12, seeks an experienced and dynamic leader to serve as Director of Development, to begin July 2025. Reporting to the Headmaster, the Director of Development is responsible for providing strategic leadership for all facets of institutional fundraising, campaign planning and implementation, and alumni affairs.
The Director of Development will establish and articulate all fundraising strategies; oversee the identification, cultivation, solicitation, and stewardship of donor prospects; oversee all development activities; and act as a liaison for the School and the community. The Director of Development serves on the School’s administrative leadership team, works directly with the Board of Trustees, and is responsible for the management and mentoring of the alumni and development office, as well as coordinating with other school departments, such as enrollment management and marketing and communications.
Leadership Searches
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Reporting to the Chief Advancement Officer, the Director of Individual Giving is a frontline fundraiser responsible for a portfolio of donors and 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 Individual Giving will oversee all individual giving vehicles, including the annual fund, major and planned giving, EITC/OSTC, and restricted giving. They will also play a critical role in increasing Church Farm School’s base through new donor acquisition efforts. A key collaborator in the leadership of the Office of Institutional Advancement, the Director will partner with the Chief Advancement Officer to set strategy and drive results on the individual giving front to increase total giving to the school from $2 million to $5+ million annually by 2030.
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The Major and Planned Giving Officer will develop a pipeline of major and planned gifts by engaging with Church Farm School’s donors, prospects, and other stakeholders to strengthen existing relationships and expand the school’s portfolio of donors. A frontline fundraiser, this role will manage a portfolio of approximately 125 major giving and/or planned giving prospects. The Major and Planned Giving Officer will play a critical role in increasing total giving to the school from $2 million to $5+ million annually by 2030.
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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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Grand River Academy an all-boys college-preparatory boarding school, seeks a compassionate and skilled School Counselor to support the emotional, social, and psychological well-being of its students. The ideal candidate will hold a degree in social work, psychology, or counseling and bring experience in providing individual and group counseling, crisis response, and case management. A commitment to supporting adolescent boys in a boarding learning environment is essential.
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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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McCallie is seeking to hire a Major Gift Officer; a professional who is proactive and demonstrates responsiveness, with a strong service mindset, independent thinking, and solid judgment in the complex and often fluid environment of independent school fundraising. This individual works closely with internal and external community partners to build engagement within a community network that fosters a strong culture of philanthropy throughout the school and global community.
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Reporting to the Director of Development, the Senior Gift Officer is responsible for programs to secure major gifts, including endowment, leadership annual fund, capital and planned gifts from all Mid-Pacific Institute constituencies. In collaboration with the Vice President of Institutional Advancement and Director of Development, the Senior Gift Officer will assist in the execution of a comprehensive major gifts plan to maximize fundraising success and primarily focus on campaign goals through external philanthropic support for Mid-Pacific.
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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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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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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 School Counselor is a collaborative and organized leader who provides individual and small-group student counseling, works with teachers and families to effectively meet student needs, and responds to emergent issues in a mission-appropriate manner.
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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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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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St. Timothy’s School, a boarding and day Episcopal school for girls offering the premier International Baccalaureate Program, seeks a dynamic and experienced Director of Development and Alumnae Relations to lead its advancement efforts.
With a rich history dating back to 1832, St. Timothy’s is deeply committed to its mission of fostering a strong sisterhood grounded in a commitment to truth, trust and kindness. The next Director of Development and Alumnae Relations will have the unique opportunity to build upon the school’s legacy and drive philanthropic engagement that ensures the school’s long-term financial sustainability. This position reports directly to the Head of School and plays a key role in shaping the school’s strategic vision by overseeing fundraising, alumnae relations, institutional advancement, and donor engagement.
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The Staff Accountant will support the mission and vision of University Liggett School through serving our Faculty and Staff within our business office function. This role is essential to our operations and will support the day to day operations through recording of journal entries, accounts payable transactions, cash deposits, etc. We are a small team so will cross-train with the Controller and Business Office Manager on various functions. We are building up this function so depending on bandwidth and capabilities will be responsible for designing better processes and documenting policies, procedures and controls.