San Francisco, California
Posted: 16-Jan-26
Location: San Jose, California
Type: Full Time
Salary: $130,000 - $155,000
Categories:
Salary Details:
Required Education:
Upper School Dean of Student Life
Start Date: July 2026
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
Student Leadership & Student Life
- 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
Program Development & Academic Leadership
- Lead the development and enactment of a twice-weekly social-emotional curriculum for the upper school advisory program, supporting faculty in their role as advisor
- Establish and lead regular student deans meetings, shaping the purpose, structure, and programming of grade-level experiences.
- Help shape a coherent, developmentally appropriate student academic life experience across grade levels, including feedback and reporting, exhibitions of learning, and student-led conferences
- Partner with Upper School leadership and student success team to develop a social-emotionally supportive and responsive program inside and outside of the classroom through advisory, HEx, Health & Wellness, grade level meetings, and other on- and off-campus programming
- Work in partnership with the school’s DEIJA team to facilitate Upper School DEIJA learning and initiatives with faculty, students, and families
- Meet regularly with the Upper School Leadership team, Head of Upper School, Student Success Team, and groups of faculty to ensure student and program success across a range of short- and long-term initiatives
School Culture & Restorative Practices
- Support the development and articulate systems that are developmentally appropriate, student growth-oriented, and school values-aligned, for responding to behavior and disciplinary concerns, including structures to encourage student growth and learning from mistakes, consequences for student infractions, and documentation and follow-up from and for faculty
- Support advisors, teachers, and/or Head of Upper School in communicating with and meeting with families about serious or persistent student concerns
- Stay current with best practices regarding student culture, restorative practice, and adolescent behavior and share such learning with senior leaders and faculty
Diversity, Equity, Inclusion, Justice, & Action
As noted in our Commitment to Community & Belonging, we strive to reflect the extraordinary diversity of Silicon Valley, believing that educational excellence and equity depend on the creation of a diverse and inclusive community where all students, families and employees feel a full sense of membership. To live up to our DEI Teaching Philosophy Statement, all employees contribute to developing culturally competent students and building an educational institution committed to social justice and reaching beyond. We offer a wide range of opportunities for all employees to engage in work that furthers these goals, from personal dialogues that help us understand different perspectives, to pedagogical training designed to support equitable instructional practices and build habits to disrupt bias whenever we see it. Ultimately, we hope that this work helps all of our constituents—employees, students, and families—be more aware, empathetic, globally-minded, and justice-oriented.
A highly collaborative community, we use the following norms to guide our communication with each other:
- Assume good will
- Come from your own experience
- Be more curious than certain
- Hold yourself and others capable
Our commitment to these norms makes it possible for us to partner meaningfully, disagree productively, and lean into conversations that are both challenging and generative.
Each and every day our students will be challenged to live out our Core Values - be kind, be curious, take risks, be your best - as they engage with an exceptional team of educators committed to helping each student reach their highest potential in school and in life. Our program is also guided by the core questions of the Scott Center for Social Entrepreneurship - “What matters to you? What are you doing about it?” Simple yet provocative, these two questions inspire all members of our community as they convey two foundational beliefs: learning must be purposeful and have enduring impact, and leveraging student interest drives both engagement and success. Hillbrook, unlike any other school, not only calls on its students to make the world a better place, but also explicitly prioritizes the skills and habits that prepare them to do so, activating and empowering students to make immediate and lasting social impact during their JK-12 years while launching them into a lifetime of social impact work.
To Apply
Salaries are competitive. Benefits include: full medical, dental, and vision coverage; ample retirement planning; a generous holiday schedule; religious/cultural holidays following each employee’s faith and background; access to the latest state-of-the-art educational technology; and a strong commitment to engaging and personalized professional development.
Hillbrook School is an Equal Opportunity Employer and seeks candidates from diverse backgrounds. Hillbrook School is committed to fostering and sustaining a learning community and does not discriminate on the basis of race, color, religion, sex, gender, sexual orientation, national origin, ancestry, age, marital status, disability, or any other characteristic protected by law. This policy applies to, but is not limited to, educational policies, admission, financial aid, hiring and employment practices, use of school facilities, athletics, and other school-administered programs and activities.
The annual salary range for this role is $130,000 - $155,000, dependent on years of experience. Please apply by submitting your resume/CV and letter of intent via this application form.
The School: Who Are We?
For almost 90 years, Hillbrook School has been a junior kindergarten-8th grade independent school located on 14 acres of oak woodland in Los Gatos, CA - and in the fall of 2023, we opened the doors to the founding class of our high school. Founded in 1935, the school remains deeply connected to its historical roots as a place where children are known, learning is authentic and active, and success is measured one child at a time. Over the years, we have grown and evolved from a small boarding school serving wards of the state to one of the leading independent schools in the Bay Area, and yet our vision remains the same—to inspire children to achieve their dreams and reach beyond themselves to make a difference in the world.
We are now embarking on one of the school’s most ambitious strategic initiatives ever: the expansion to a JK-12 with the addition of a new high school in downtown San José. We are driven by a foundational belief - that our 8th graders and other students deserve an extraordinary educational experience in high school that builds upon the exceptional foundation we provide our JK-8 students. The core differentiators for our current program - the placement of choice and engagement at the center of the learning experience, integrated, real world education that challenges students to reach beyond and make a difference, and a deep commitment to diversity, equity and inclusion - will translate seamlessly into a 9-12 environment, allowing us to extend our innovative approach into a market in need of a new model of secondary school education.
Location
Hillbrook has two campuses located in Los Gatos and San José. These locations in the heart of Silicon Valley are 35 minutes south of Stanford University, 30 minutes north of Santa Cruz, and 1 hour south of San Francisco. The Bay Area is home to world-class universities, museums and restaurants, farmers markets and wineries, and outstanding outdoor opportunities for biking, hiking, surfing and more.
Qualifications
- Desire and ability to work in a collegial, highly collaborative environment.
- Demonstrated commitment to teaching and learning in a diverse, dynamic, and progressive school community.
- A commitment to anti-racism and demonstrated skill in designing equitable and inclusive educational experiences and learning environments that incorporate themes of diversity and justice.
- Experience in a high school–level leadership role supporting student life, student support, and school culture, with responsibility for designing, coordinating, and sustaining programs for adolescents and families.
- Experience partnering closely with students as leaders and collaborators, and working with faculty to develop and support advisory, social-emotional learning, and student support practices.
- Bachelor’s degree required; Master’s degree preferred.