Head of School
OPPORTUNITY STATEMENT
The Opportunity Women Learning, Women Leading Nestled on six acres in residential Palo Alto, California, Castilleja School empowers young women to chart an ambitious course for their education and beyond. The school’s faculty and students are authentic partners in learning in a community that embraces academic excellence, innovation, and bold ideas.
intellectually curious, and inspirational leader, the next Head will bring an unwavering focus on excellence, equity, and the vital importance of women’s education. They will relish the opportunity to partner with a talented faculty as they seek to extend Castilleja’s nationally recognized leadership in these areas.
Over generations, “The Circle”—Castilleja’s interior courtyard—has become a symbol of the school’s inclusive and supportive culture. Here, the employees and students join together in intentional, joyful ways as the girls fulfill the school’s mission: to become confident thinkers and compassionate leaders with a sense of purpose to effect change in the world.
As the school’s executive leader, community leader, and chief academic strategist, Castilleja’s next Head of School will bring the sophistication and experience to balance an agenda that includes continued attraction of the highest quality students and faculty, a major construction project, ongoing educational innovation, support for the social and emotional well-being of young women, and bold advocacy and support for social justice. In support of its overall mission, Castilleja’s next Head of School will engage generously and authentically with its alums, parents and guardians, and neighbors. This leader will forge Castilleja’s enduring values with the dynamic educational environment to ensure a school that continues to meet the evolving needs of today’s students.
The Castilleja Board of Trustees seeks a leader with the vision, energy, and shared values to write the next chapter of Castilleja’s history, including the immediate construction of a long-awaited modernized campus; investments in strengthening the community for all its members; and the advancement of the school’s program—both academic and co-curricular— in thoughtful, innovative ways. A student-centered, 2
IDEAL EXPERIENCE Castilleja’s next Head will possess high intellect and integrity, as well as expansive leadership skills. This educator will bring executive leadership experience to steward the school’s assets, to nurture a sense of community, to communicate with passion and clarity, and to take on challenging conversations and make difficult decisions. In addition, the Head will bring the joy, empathy, and curiosity required to lead an institution that serves dynamic, kind, intellectually engaged students; talented and dedicated employees; and devoted alums. As such, the Search Committee seeks an individual with a demonstrated ability to: • Provide vision, strategic leadership, and insight to advance the school towards its highest aspirations and goals. • Embrace the enduring values of girls’ education and the ability to articulate its strength to others. • Engage intellectually with faculty and gain their confidence through a commitment to academic excellence, exceptional teaching, and foundational support for the whole child. • Develop collaborative, trusting relationships with students, employees, parents and guardians, and alums. • Innovate and develop new ways to forge community bonds at Castilleja and provide the emotional and academic support for members of the Castilleja community. • Inspire, support, and drive impactful engagement on issues of social justice, equity, and inclusion including driving change in the organizational culture, systems, and practices. • Attract philanthropic support for the school’s ambitions, forge the relationships and have the storytelling skills needed to inspire donors and alums. • Steward the financial and physical assets wisely, making decisions always in the best interest of the institution. • Communicate exceptionally and listen well, with the ability to engage effectively with a wide range of constituents. • Bring resilience, stamina, and strength for the pressures of the role.
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CRITICAL LEADERSHIP CAPABILITIES Bold Educational Leader with a Deep Passion for Girls’ Education The next Head of Castilleja will join the school at a critical inflection point: with the construction of the reimagined campus underway, the desire to explore and clarify the strategic priorities, and a culture that leans towards innovation, the Head will lead the Board and the employees in discussions of the continued evolution of the school and its programs. The Head will partner with the faculty to review, refine, and strengthen the current program while setting and realizing future initiatives that will enhance the already exceptional school. Informed by research and with a keen focus on what Castilleja graduates need to learn to thrive, the Head will encourage bold questions, welcome discussions, and launch initiatives to continuously strengthen the educational experience for the students. The Head will be determined in their quest to create an environment and programs that support the social, emotional, and personal growth of the students. A voracious learner, coalition builder, and the lead advocate of a top-notch girls’ school, the Head will relish the opportunity to live, work in, and engage this growth-focused community. Collaborative Leadership and Community Building At a small school with meaningful, enduring relationships, the next Head will be a community-oriented leader who embraces, respects, and supports the school’s commitment to and reliance upon its tightly knit community. An empathetic, accessible leader, the Head will build rapport, trust, and genuine relationships with students, faculty, staff, parents and guardians, and alums. A visible presence in the community and life of the campus, the Head will relish the opportunity to walk the campus, attend classes, performances, and athletic events, and to get to know the students. In collaboration with colleagues, they will work to ensure that all students feel seen and known and a share a sense of belonging. They will champion the diversity of the school and ensure that Castilleja continues its intentional, deeply held commitment to equity, inclusion, anti-racism, and social justice. The Head will communicate with frequency and transparency, listen with compassion and curiosity, and understand that their daily actions reinforce the community’s values. Organizational Stewardship To accomplish the ambitious agenda at an ambitious school in the most innovative part of the country, Castilleja School’s next Head must be a sophisticated steward of institutional assets with strong business acumen, effective managerial skills, agility, and impeccable judgment. The Head will attract and retain top talent on the faculty and staff and will create an organizational structure and environment where people are empowered, supported, and held accountable. The next Head will understand the importance of aligning resources with aspirations and will set a strategic plan that is both ambitious and sustainable. In considering important issues, the leader will welcome debate, listen carefully to different perspectives, and be willing to make tough decisions as needed. As a passionate advocate for Castilleja, the next Head will engage community members in continuing to build institutional and philanthropic support to achieve its mission and will develop respectful partnerships with its neighbors. In all matters, the Head will shepherd the school in ways that enhance the experience of students at Castilleja. 4
SEARCH PROCESS Castilleja School is an equal opportunity employer and makes employment decisions based on merit, qualifications, and competence. Castilleja prohibits discrimination based on race (including traits historically associated with race, including, but not limited to, hair texture and protective hairstyles), color, creed, gender (including transgender, gender identity and gender expression), religion, marital status, registered domestic partner status, age, national origin or ancestry, physical or mental disability, medical condition, pregnancy, genetic information, sexual orientation, or any other consideration made unlawful by federal, state, or local laws. It also prohibits
discrimination based on the perception that anyone has any of these characteristics, or is associated with a person who has, or is perceived as having, any of these characteristics. Castilleja School is being assisted by Spencer Stuart in the search process. The committee welcomes comments, questions, nominations, or expressions of interest. Please send expressions of interest with any supporting materials to the following confidential email address: CastillejaHOS@spencerstuart.com.
OTHER PERSONAL CHARACTERISTICS • Embodies the school’s values, also known as the 5Cs: courage, conscience, courtesy, charity, and character. • Engages questions with broad intellectual curiosity. • Is culturally competent and open minded, with the ability to understand, respect, and develop meaningful relationships with people from various backgrounds and experiences. • Communicates with exceptional verbal and written skills to offer thoughtful, inspiring, and authentic insights. • Possesses the confidence to mentor others and share credit. • Thrives in the energy of a school with a positive and optimistic outlook and a love for being around young people.
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About the School Castilleja is the only 6–12 nonsectarian school for girls in Northern California, serving 416 students in the heart of Silicon Valley in Palo Alto. The consummate educators at Castilleja inspire intellectual curiosity, nurture belonging, and empower girls to explore bold questions. Graduates leave with perspective and the knowledge they need to lead for good in a diverse world, fully understanding that they not only deserve a seat at the table, but they are also capable of chairing that table. Founded in 1907 with the mission to prepare young women for college, Castilleja now seeks to prepare them to become confident thinkers and compassionate leaders with a sense of purpose to effect positive change. Situated on just over six acres in and organized around “the Circle,” the greenspace at the center of campus, Middle School (Grades 6–8) and Upper School (Grades 9–12) students benefit from being steps away from the vast and varied resources of Stanford University, just down the road from the world’s tech giants, including Apple, Google, and Meta, and within 6
reach of two major cities, San Francisco and San Jose. Sixty-nine percent of students self-identify as people of color, and drawing from 31 communities through the Bay Area, they speak 21 languages at home. Twentyone percent of students receive tuition assistance, with an emphasis on first-generation families. Given its location, Castilleja is particularly aware of the importance of addressing gender disparities in technology through its award-winning robotics program, Advanced Topics STEM courses, and partnerships with local mentors. At the same time, for generations Castilleja has been recognized for academic rigor in the humanities, producing politicians, artists, and scholars who have made lasting impacts. The talented adults at Castilleja—including teaching faculty, program directors, counselors, and coaches— believe the world needs more women leaders and see potential for leadership in every student. Across disciplines and inside and outside the classroom, they work to ensure that every student can set exciting goals and fulfill them. There are 62 full and part-time faculty.
Among the faculty and staff, 87% hold advanced degrees with 35% identifying as people of color. The student-faculty ratio is 7:1, and the average class size is 15. The community is guided by the values of the 5Cs: courage, conscience, courtesy, charity, and character. Castilleja’s program is infused with hands-on, interdisciplinary experiential learning opportunities that expose students to bold questions. This happens within the classroom, with seniors taking on deep-dive projects that prepare them for upper-level college coursework in AT Research and Writing in History and Social Sciences, and 6th grade students negotiating to represent different countries’ interests in relation to the UN Sustainable Development Goals. Outside the classroom, students participate in musical, theatrical, and dance performances, and join our competitive athletics program, which sends students on to thrive as collegiate athletes. Learning and leading is also propelled by different program hubs, including work in the robotics and maker space in the Bourn Lab, collaborative projects in the Library, and community and global engagement through the Center for Awareness, Compassion, and Engagement (ACE). Whether within the ACE Center, including partnerships with local nonprofits and Global Investigator Trips, through student leadership in affinity spaces and political advocacy, or through direct instruction in the classroom, Castilleja’s program is informed by a commitment to DEIJ and belonging. Castilleja’s Diversity and Inclusion Statement calls on every community member to engage differences with courage, honesty, and respect and sees a commitment to diversity and inclusion as an essential foundation for leadership. Throughout their time at Castilleja, students explore Leadership Competencies, such as Curiosity, Collaboration, and Empathy, and Antiracist Competencies, such as Valuing Multiple Narratives, Committing to Rewire, and Understanding Positionality. Together, these concepts provide a thoughtful scaffolding to assure that DEIJ and belonging are built into the student experience throughout all the grades, all the disciplines, and all the different learning environments. Located in a beautiful neighborhood in historic Old Palo Alto, Castilleja has recently gained city approval of a new Master Plan to modernize the campus and gradually increase enrollment. This project will break ground on an underground garage in the summer of 2024. At the close of the 2024–25 academic year, the field above the garage will become home to Castilleja Village, two-story temporary buildings where classes will take place while the sustainable learning spaces that will carry the institution into the next century are built. The projected completion date is during the 2027–28 academic year and will continue to advance Castilleja’s stellar program, with sustainable, flexible, light-filled spaces that will break down barriers between
disciplines and between the indoors and the outdoors, creating opportunities for students to fully understand learning as an open, creative, and limitless process. The final crucial element of the campus update relates to the community. On a concrete level, this longawaited modernization will create the spaces that will serve to attract the finest faculty and students. On an even deeper level, though, this project will transform Castilleja by allowing for increased enrollment with an opportunity to grow from 416 students to as many as 540 students. This shift will enrich the Castilleja community by increasing diversity in the student body, bringing new voices into the classroom and creating an even more dynamic learning environment with new courses and teams. At the same time, this will also enhance the broader Bay Area community by opening this transformational educational opportunity to more students. Since its founding, Castilleja has consistently benefited from strong philanthropic partnerships with parents, past parents, and alums whose belief in the mission and vision of the school have inspired one family to underwrite the entire Computer Science program and another to endow all of the Global Investigator Trips. Castilleja recently received the largest donation from a single family to an independent school in the Bay Area, and the school is now entering the public phase of the most ambitious capital campaign in its history, with a goal of raising $125 million for the campus modernization. After graduating, alums become faithful donors, but with achievements that include being counted among the Forbes 30 Under 30 list, being named to the National Academy of Sciences, and being appointed as a U.S District Judge, their time and expertise are also very valuable. They share it willingly by returning to campus to sit on panels and serve as mentors for current students, and they consistently speak of their deep appreciation of the lifelong friendships they developed around the Circle. The most recent strategic plan, titled “What’s Possible?” set out a bold outline of goals for the future while asserting that relationships are the heart of Castilleja. This thesis has proven to be true as the school weathers a season of change. The relationships and traditions that bring the community together are stronger than ever, as is the commitment to providing an outstanding education to the next generation. As a collective, the Castilleja community is defining the future of women’s leadership by living its values of inclusion and belonging, recognizing that sustainable change is based in collaboration, and educating students to make unique choices to pursue lifelong learning and well-being. Castilleja is the rare school where girls hold all the leadership roles and there’s a strong commitment to student mentorship. Graduates leave knowing how to both support and inspire each other to exceed and redefine expectations. 7
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