Castilleja School
12-month position beginning July 2025

Castilleja School seeks a passionate, experienced educator to serve as Upper School Dean of Students. The Dean of Students will be an experienced educator who provides thoughtful leadership while establishing a clear, inspiring vision for student programming that fosters joy, aligns with the school's mission of educating young women to become confident thinkers and compassionate leaders, and strengthens community throughout the school. With the support of a team of class deans, the Dean of Students reports to the Head of the Upper School, leads the Student Support Team, and serves as an advocate for individual students and the Upper School student body as a whole.

Key Responsibilities

• Develops and refines the advisory program with a clear, mission-aligned, girl-centered vision that nurtures confident thinkers and compassionate leaders who are seen and known deeply by advisors and class deans
• Leads and collaborates with class deans to foster student well-being, implement meaningful activities, coordinate orientations, handle logistics, and uphold cherished school traditions
• Maintains a visible presence and builds meaningful relationships throughout campus, staying deeply connected to the student experience to effectively advocate for student needs and perspectives 
• Monitors the impact of school initiatives on student life and partners with other employees and departments to develop programs that support students' development and well-being
• Partners with Upper School counselors, DEI practitioners, ACE Center and wellness faculty on implementing SEL programming and leadership curriculum
• Collaborates with counseling staff and class deans to plan parent/guardian education for all grade levels
• Supports the Head of Upper School in serving as a liaison between families and the school
• Partners with academic leadership to ensure comprehensive and coordinated student support
• Facilitates coordination with Middle School leadership for consistent and coordinated events, activities, and programs across grades 6-12
• Serves as a class dean, offering direct mentorship to a specific grade level while coordinating class-specific activities, guiding student government, and organizing grade-level programming 
• Implements a student-centered approach to upholding the Upper School Code of Conduct grounded in the School's mission, values, and restorative practices
• Facilitates courageous conversations and communicates clearly and promptly with students, parents, and appropriate school staff
• Other student-related duties may be assigned according to talent and experience

• Bachelor's Degree required; Master's degree preferred in education or counseling
• Leadership experience or project leadership in a school setting
• Experience teaching at the upper school level and/or familiarity with teaching in independent schools
• A deep commitment to girls’ education 
• Experience with restorative practices and conflict resolution
• Ability to navigate difficult conversations with students, parents, and colleagues
• Superior executive skills and ability to work with a high level of consistency and integrity
• Commitment to partnering with other departments and colleagues
• A sense of humor and optimism and commitment to believing in each student's ability to learn and grow

Salary Range: $130,000-$160,000

Application Instructions: Please include a Cover Letter and apply via the School's Career page.