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Upper School Dean of Student Life

Job in Los Gatos, Santa Clara County, California, 95032, USA
Listing for: Hillbrook School
Contract position
Listed on 2026-01-26
Job specializations:
  • Education / Teaching
    School Counselor, School Principal, Education Administration, Academic
Salary/Wage Range or Industry Benchmark: 80000 - 100000 USD Yearly USD 80000.00 100000.00 YEAR
Job Description & How to Apply Below

VISION
:
Inspire students to achieve their dreams and reach beyond themselves to make a difference in the world.

MISSION
:
Hillbrook provides an extraordinary educational experience that fosters a love of learning in our students and helps them develop the knowledge, skills, and confidence to achieve their highest individual potential in school and in life. At Hillbrook, students are known, respected and valued as individuals and every day is a journey of self-discovery, imaginative thinking, creative problem solving, laughter and friendship.

CORE VALUES
:
Be kind. Be curious. Take risks. Be your best.

The Position:
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:

  • Partner with students to lead Upper School student life
    , including student clubs, field trips, school events, advisory, all-school meetings, and Student Council, in ways that support student agency, wellness, and social impact.
  • Cultivate student leadership and community engagement by supporting student voice, shared responsibility, and meaningful participation across the Upper School.
  • Guide the student academic life experience
    , including the course planning process, narrative feedback, exhibitions of learning, and student-led conferences and presentations of learning.
  • Establish and refine an Upper School advisory program grounded in students’ developmental needs
    , supporting teachers in enacting advisory practices that integrate academic, social-emotional, and co-curricular experiences.
  • Lead the development and enactment of a school-wide philosophy of restorative practice
    , ensuring students and faculty are supported in applying restorative approaches that promote accountability, repair, and growth.
  • Cultivate a positive Upper School culture grounded in the school’s core values:
    Be Kind, Be Curious, Take Risks, and Be Your Best.
The Hillbrook Employee:
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.

Specific Duties and Responsibilities
  • 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…
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