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Be Kind. Be Curious. Take Risks. Be your Best.

Founding Director of College Counseling

Hillbrook School is seeking a full-time founding Director of College Counseling for the high school to be opened, starting with a class of 9th graders, in Fall 2023. Reporting to the Upper School Head, the Director of College Counseling will oversee the creation of a college counseling process during the course of the school’s early years, assuming oversight for all aspects of the college counseling process. In addition, the Director will collaborate closely with the Head of Upper School and the founding team to design a program that prepares students for success in college, and provides a course of study that ensures students are UC-eligible upon graduation.  This position begins on July 1, 2022.

For more than 85 years, Hillbrook School has been a junior kindergarten-8th grade independent school located on 14 acres of oak woodland in Los Gatos, CA. 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. 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.

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 campus in Downtown San Jose. We are driven by a foundational belief – that our graduates and other students deserve to have an extraordinary educational experience in high school that builds upon the exceptional foundation we provide for 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 in the world, and a deep commitment to diversity, equity and inclusion – will translate seamlessly into a 9-12 environment, allowing us to extend our innovative approach to education into a market in need of a new model of secondary school education.

In our market, while there are a variety of high school options, there are none that look like the model – a small, independent high school connected to a JK-8 – we envision for Hillbrook. The benefits of top independent schools around the Bay Area and the country are well known – environments in which students are known and valued, educational programs that combine academic challenge with meaningful engagement, co-curricular programs that are excellent and inclusive, and results, including traditional results like college placements and standardized test scores, that are stronger than any other type of school. We are confident that a Hillbrook Secondary School will, like other peer, progressive independent schools across the Bay Area and country, provide an extraordinary educational experience that creates a pathway for students to excel both in school and in life.

Hillbrook High School will align with leading independent schools like Castilleja, Woodside Priory, Menlo School, Nueva, and The Urban School of San Francisco. As a group, these schools:

  • Have higher ACT/ SAT scores and stronger college placement records than any of the Catholic or public options currently in our market.
  • Are smaller than any of our current local options, with class size ranging from the low 60s (Castilleja and Woodside Priory) to the mid-100s (Menlo School).
  • Create a rigorous, engaging, and balanced academic experience that leads to graduates who are committed to changing the world for the better.

As noted in our Statement of Inclusivity, 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 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. The high school campus will be situated in downtown San José.

The Director will have primary responsibility for building a college counseling program that supports students in getting into a right-fit school, while also supporting families’ engagement and understanding of the process.


  • Design and oversee the college search and application process for an Upper School that will eventually reach 260-300 students, building programs in the early years that are provide students and families with a healthy and effective level of support and guidance
  • Work closely with the Upper School Head and other members of the founding team to design a curriculum that builds upon Hillbrook’s JK-8 and provides a challenging, college-preparatory program that ensures students are prepared for top schools across the country, including the UC system
  • Develop and maintain relationships with students, seeking opportunities to engage with them both inside and outside the classroom
  • Actively develop relationships between Hillbrook and colleges and universities, starting in year zero, prior to the opening of the school and admission of the first 9th grade class.
  • Work with the Enrollment & Communications team to share with parents how the school will support students in the college process and reassure parents of the benefits and opportunities that exist when joining a newly created high school attached to a longstanding JK-8


  • Five years of admission and financial aid experience at the college or university level or five years of college counseling experience at a private, independent school
  • Experience in communicating a complex subject to a variety of audiences, both in written and verbal forms
  • Experience and demonstrated enthusiasm for developing and designing new programs
  • Enthusiasm for a role that involves significant travel and a broad range of events outside of typical school hours
  • An open and collaborative management style combined with an ability to be a decision-maker
  • Strong passion for the role and the school, and an understanding of how the position supports the school’s ability to meet its mission and vision every day
  • Ability to work in a collegial, collaborative environment and to develop the necessary trust and credibility to work with faculty, administrators, and parents
  • Ability to facilitate and engage in difficult conversations and coach others to do the same
  • Excellent interpersonal, written and verbal communication skills
  • A growth mindset, active sense of humor, warm personality, and excellent organizational skills
  • Advanced degree preferred

Salaries are competitive. Benefits include: full medical, dental, and vision coverage; ample retirement planning with TIAA-CREF; a generous holiday schedule; religious and cultural 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 disability.

Visit our school’s website to learn more at Interested candidates should send a cover letter and resume as .pdf files to Director of Human Resources, Rozanne Schiro.

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