Highland School seeks a dynamic, talented, and strategic leader to serve as our Director of Development. This full-time, 12-month senior administrator reports to the Assistant Head for Institutional Advancement and will collaborate closely with the Head of School, the Board of Trustees, and other Highland constituents. The Director will oversee all of Highland’s fundraising efforts, including but not limited to annual giving, major gifts, and leading the campaign for Highland’s 100-year celebration in 2028. The Director will supervise two advancement staff: the Director of Annual Fund and the Director of Special Events & Alumni Relations.

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PREFERRED QUALITIES AND QUALIFICATIONS

• Bachelor’s degree and experience working in a high-functioning advancement office.
• Demonstrated experience collaborating in planning, executing, and leading an effective capital or endowment campaign. 
• Experience in education fundraising. 
• Established connections within the Highland School and/or Virginia Piedmont communities.
• Management experience for the successful leadership of the advancement staff, with the skills, training, and competence to mentor staff and colleagues.
• Understanding of the entrepreneurial mindset needed to lead a small but high-functioning development team.
• Intellectual depth, moral integrity, vision, energy, and a sense of humor.
• Ability to maintain confidentiality and sensitivity.
• Working knowledge of the Google Suite, Microsoft Word, Excel, and Blackbaud’s relationship management software.

About Highland School

Located halfway between Washington, D.C., and the beautiful Shenandoah National Park, Highland School boasts state-of-the-art facilities in the heart of Warrenton, Virginia. A thoroughly modern campus serves families and students in Pre-Kindergarten through 12th grade from a broad geographic area. Surrounded by charm and rural warmth, the campus includes the renowned Michael A. Hughes Center for the Arts (home of the Piedmont Symphony Orchestra), the LEED-certified William A. Hazel Family Lower School, a new Middle School Outdoor Classroom, and recent upgrades to the libraries and media centers of the Upper and Middle Schools. Founded in 1928, Highland School is impressive by any standard. The campus is intentionally designed to enhance the pursuit of academics, athletics, and fine and performing arts. The facilities are the perfect environment to support the school’s mission: “to prepare students to thrive, lead, and serve in a diverse and dynamic world.”

Connections working at Highland School