Highland School
Warrenton, VA
Grades PK - 12 with 500 students


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The Upper School Dean of Student Life and Leadership reports to the Upper School Director and is responsible for advancing the following institutional priorities:

  • Foster a positive school culture in alignment with Mission, Inclusivity, and Philosophy statements;

  • Coordinate with grade level deans and mentor student leaders to promote an engaged community and comprehensive student leadership development; 

  • Handle serious student discipline matters and resulting communications;

  • Direct the administration of the honor system and honor education process;

  • Centralize coordination of field studies programming, collaborate with grade level deans to renew and implement an integrated sequence of experiences, and contribute to chaperoning;

  • Organize spirit, community building, and leadership formation/demonstration activities across grade levels;

  • Serve as coordinator for the Leadership Certificate program.


Specific responsibilities that support these priorities include the following:

  • Designs new and reimagines existing programs and initiatives to increase student access to impactful leadership formation and opportunities to exercise leadership;

  • Thoughtfully and consistently addresses major conduct issues, especially those that violate the school’s Honor Code, following up with parents & students;

  • Communicates with faculty, students, and parents regarding community life and maintains records of student conduct, honor, and attendance issues; 

  • Works as a member of the Student Support Team to identify and provide support for students experiencing academic and/or personal difficulties;

  • Mentors the Prefect Board and directs the Honor Council;

  • Organizes the Advisory program, including providing meaningful activities for Advisories; 

  • Helps plan and implement Assemblies that shape school culture and showcase student engagement;

  • Works with student leaders and faculty sponsors to organize and maintain Clubs; 

  • Coordinates with relevant grade level dean on major Upper School social events such as the homecoming dance and spring formal and fundraising efforts such as lunch; 

  • Serves in admissions programs such as Open House, hosting/interviewing visiting applicants; and academic planning nights;

  • Teaches three sections.

Position also includes other duties as required to support the advancement of Highland School.

Already an active candidate? Contact your counselor!

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