Upper School Dean of Student Life
Listed on 2026-01-22
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Education / Teaching
School Principal, School Counselor, Education Administration, Guidance Counselor: Social/Educational
Upper School Dean of Student Life
Start Date:
July 2026
What Will You Do & How Will We Collaborate?
Hillbrook Upper School is entering its fourth year of operation and its first year of 12th grade. This is a formative moment for the school, with core structures in place and continued opportunities for the Dean of Student Life to refine, strengthen, and create systems that will shape the student experience, school culture, and program coherence over time.
The Dean of Student Life is a member of the Upper School Leadership Team, and reports to the Head of Upper School on a 12-month contract. The Dean of Student Life works closely with the Head of Upper School on all aspects of student life including: student culture, climate, curricular and co-curricular options, and discipline. In this role, the Dean has broad responsibility across several core domains:
, including student clubs, field trips, school events, advisory, all‑school meetings, and Student Council, in ways that support student agency, wellness, and social impact.
, including the course planning process, narrative feedback, exhibitions of learning, and student‑led conferences and presentations of learning.
, supporting teachers in enacting advisory practices that integrate academic, social‑emotional, and co‑curricular experiences.
, ensuring students and faculty are supported in applying restorative approaches that promote accountability, repair, and growth.
Be Kind, Be Curious, Take Risks, and Be Your Best.
Who Are You?
Do our Core Values – Be kind. Be curious. Take risks. Be your best. – align with how you show up as a professional? Are you committed to building and bridging inclusive communities? Do you believe learning should be an active and relational process? Do you enjoy nurturing and maintaining best practices and continuity of programs, while also evolving programs in response to new information?
Is equity and impact at the forefront of what you do? Are you entrepreneurial? Do you thrive in small collaborative environments? Do you seek opportunities for interdisciplinary, experiential learning? Do you believe that students are capable changemakers at any age and stage? A Hillbrook employee will emphatically say yes to each of these questions.
- Coordinate and support students in establishing and leading all‑school meetings and student life initiatives such as student clubs, dances, and on‑ and off‑campus events, with responsibility for scheduling and budget support
- Support Student Council in planning and facilitating student programming, including all‑school and grade‑level events throughout the year.
- Establish and support school‑wide approaches to student leadership development, ensuring all students have opportunities to build leadership skills and agency across grade levels.
- Support students in understanding and advancing DEIJA‑related initiatives within student life and school culture.
- Support the design and establishment of a Senior Year experience for students, including graduation, senior prom, and spirited activities that celebrate and spotlight student successes and achievements
- Serve as the primary point of contact for Upper School Reach Beyond Scholar (RBS) students and families, supporting orientation, communication, and retention
- Partner with Upper School faculty and Upper School Leadership Team to establish programs and structures that contribute positively to student life
- Lead the development and enactment of a twice‑weekly social‑emotional curriculum for the upper school…
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