The full-time equivalent salary range for this position is $175,000. - $225,000. The starting salary is based upon, but not limited to, several factors that include years of experience, education level, and expertise.
Preferred Education:
Masters
Head of Upper School
Start Date: July 2025
Mission Statement
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.
Vision Inspire students to achieve their dreams and reach beyond themselves to make a difference inthe world.
Overview
For 90 years, Hillbrook School has provided an extraordinary K-8 educational experience that inspireschildren to achieve their dreams and reach beyond themselves to make a difference in the world.From the beginning, Hillbrook has known that the most authentic and meaningful education happenswhen student choice and engagement are at the center of the learning experience.Nearly 10 years ago, Head of School Mark Silver, his leadership team, and a committed Board ofTrustees developed a vision for a transformation of Hillbrook from a JK-8 into a JK-12 with two campuses,three divisions, and one unified vision. They envisioned an Upper School that embodied the school’scommitment to reach beyond and make a difference in the world, designing a program that providedthe highest levels of academic challenge in an environment in which students are allowed to thrive aschange agents and engaged citizens.
Hillbrook's vision is now a nascent upper school of seventy-two 9thand 10th grade students in downtown San Jose - built on the foundation of the school’s core questions
– What matters to you? What are you doing about it?
Hillbrook School seeks a Head of Upper School to continue the exciting work of co-creating the new division.
Opportunities and Challenges
The next Head of Upper School will bring an entrepreneurial spirit and a commitment to progressive education to the energizing and challenging work of bringing Hillbrook’s vision to fruition The Head of Upper School will:
Steward the Expansion
The Head of Upper School will continue to build an upper school program that aligns with Hillbrook’s mission and core values and focuses on high level engagement in the classroom, close student-teacher relationships, and signature Reach Beyond programs like Immersives, which embrace the city as classroom and foster student agency through community engagement, internships, and apprenticeships.
From the expansiveness of vision to the details of course offerings, from faculty culture to student life, the Head of Upper School will be present, engaged, reflective, and responsive to the complexities of an evolving division.
Work Collaboratively with the Hillbrook Leadership Team
Many of Hillbrook’s seasoned leadership team members have served the school for more than a decade and stand by their conviction that collaboration produces better outcomes for all. They hold the mission and core values of Hillbrook at the center of their work and serve as essential teammates for the Head of Upper School as the division develops and refines Hillbrook’s progressive, student-centered curriculum, builds systems, hires essential personnel to grow the division’s faculty and administrative structure and responds to constituent feedback. Lone rangers need not apply.
Build Culture and Community
With the completion of the Moir Building and the expansion of the student body to grade 11, the division will continue its exciting evolution in the 2025-2026 school year. The Head of Upper School will guide the community and welcome their voices in continuing to build the norms and rituals that weave the fabric of the upper school. Hillbrook’s mission, vision, and core values - be kind, be curious, take risks, do your best – already guide the community, and the Head of Upper School will continue to hold these values at the center of the evolving culture while embracing the three divisions, two campuses, one school identity of Hillbrook.
Utilize Faculty Wisdom and Talent
The nascent upper school has drawn talented and experienced educators to Hillbrook’s expansion. Co-creators in spirit, dedication, and creativity, they are eager to collaborate as the division expands, introduces new programs, and continues to refine pedagogy and curriculum. The next leader will prioritize collaboration with this invaluable team, carving out time for the adults to dig into their work together and benefit from the experience and wisdom of the group.
Balance Vision and Implementation
The next leader will have the ability to communicate the vision for the future of the upper school while holding space for the necessary reflection and revision that comes with building a new division. Central to this work will be the ability to establish priorities and assess the bandwidth of the team as the division welcomes new students and adds program.
Tell the Story and Cultivate Other Storytellers
The Head of Upper School will know the life of the division and be a storyteller who can demonstrate the vision in action and celebrate the students’ and professional community’s successes with Hillbrook families, prospective families, colleges, and community organizations.
The Head of Upper School will also develop and empower the division’s other voices to skillfully connect their stories with signature programs and Hillbrook’s mission and core values.
Bridge the Divisions
Hillbrook has a long history and a stellar reputation as a PK-8 school. With the new division on a separate campus about 10 miles from the PK-8 campus, the Head of Upper School will hold the throughlines that define Hillbrook’s curriculum, pedagogy, and culture while building age-appropriate programming for high school students and seeking ways for teachers, staff, students, and parents to share experiences across divisions.
Qualifications and Personal Attributes
A passionate belief in and experience developing and managing the delivery of a progressive, student-centered, and competency based high school education
Exceptional interpersonal and communications skills, including the ability to listen carefully and reflectively, speak confidently and persuasively, and write skillfully to the full range of school constituencies
A builder of mission-aligned systems and structures needed during an expansion’s second phase
The ability to manage an expansive agenda by delegating, appropriately calibrating the pace of change, and identifying the resources required
A track record of building a diverse, inclusive, and collaborative organization
Significant and successful classroom teaching experience and demonstrated success as an effective instructional leader and manager
Grounded and fluent in cultural competency, equity, and inclusion work
A confident decision maker and strong communicator of why
Strength in building and maintaining connections and community between colleagues, divisions, parents, and students
Thorough and demonstrated understanding of and love for working with students with great energy, warmth, and humor
Able to manage a range of personalities with strong EQ and emotional bandwidth
A sense of humor.
To Apply
Salaries are competitive. Benefits include: full medical, dental, and vision coverage; ample retirement planning with TIAA; 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 full-time equivalent salary range for this position is $175,000. - $225,000. The starting salary is based upon, but not limited to,several factors that include years of experience, education level, and expertise.
Hillbrook School has engaged Carney Sandoe & Associates to lead the Head of Upper School search. Interested and qualified candidates are invited to contact the consultants in confidence to Karen Whitaker, Senior Consultant at karen.whitaker@carneysandoe.com and Chris Boyle, Consultant at chris.boyle@carneysandoe.com
Learn More
Click on the links below to learn more about Hillbrook School.
Hillbrook School is a junior kindergarten-12th grade independent school located on 14 acres of oak woodland in Los Gatos, CA and in downtown San Jose. Founded in 1935, Hillbrook School remains deeply connected to its historical roots as a school where children are known, learning is authentic and active, and success is measured one child at a time. During the past 85+ 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. Our talented faculty delivers a program that provides 380+ students of all genders with a unique blend of challenging and engaging academics, diversity, equity, and inclusion practices, visual and performing arts, physical and wellness education, passion-driven projects, and opportunities to serve and partner with others in our community beyond campus.
Hillbrook School is a recognized leader in innovation, earning designation since 2010 as an Apple Distinguished School. Our 1:1 iPad program, Hub Makerspace, Center for Teaching E...xcellence, and Scott Center for Social Entrepreneurship all stem from a commitment to implementing best practices in education. Our faculty members present at conferences across the globe each year on topics ranging from ways we have audited our curriculum for greater inclusion to research studies conducted on-campus examining the impacts of classroom design on learning. A community of highly engaged, lifelong learners, Hillbrook is intentional about, and deeply committed to, collaboration and professional growth in all facets and roles.
As noted in our Statement of Inclusivity, we strive to reflect the extraordinary diversity of Silicon Valley, and believe 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 JK-8 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.
Hillbrook is located in the heart of Silicon Valley, 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.
Salaries are competitive. Benefits include: full medical, dental, and vision coverage; ample retirement planning with TIAA-CREF; a generous holiday schedule; religious holidays following each employee’s faith; 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. Opportunities are open to all individuals without regard to race, religion, national origin, gender, sexual orientation, marital status, age, or handicap.