Head of School Search

In late October 2021, Crossroads School’s Board of Trustees approved the appointment of Colleen O’Boyle as the next head of school. Colleen will step into the role on July 1, 2022, succeeding Bob Riddle, who first joined Crossroads in 1984 and has led the School since 2009.

Announcing Our Next Head of School

A Message from the Board Chair
Nov. 2, 2021

Dear Crossroads Community,

On behalf of Crossroads School’s Board of Trustees, I am thrilled to announce that Colleen O’Boyle will be our next head of school, effective July 1, 2022.

Colleen was selected after a highly competitive national search overseen by the Board’s Search Committee in collaboration with the consulting firm Resource Group 175 (RG175). Last April, RG175 sent the Crossroads community a survey to help identify the skills and characteristics required in the next head of school. In Colleen, we found a candidate who embodies those attributes and more. She is an accomplished administrator in a large, metropolitan school; a passionate advocate for diversity and inclusion; an experienced progressive educator; and a visionary leader eager to embrace Crossroads’ past while illuminating the path to the future. The feedback we received from the faculty, staff, administrators, parents and students who met with her during her campus visit was overwhelmingly positive. The Search Committee enthusiastically recommended Colleen to the full Board of Trustees, which voted unanimously to ask her to be our new head of school.

Colleen is currently in her fifth year as assistant head of academics at La Jolla Country Day School (LJCDS), which serves students from ages 3 through 12th grade. Her direct reports include three division heads as well as the directors of arts, athletics and learning resources. She also oversees the school’s centers for excellence in design & innovation, citizenship and wellness. Additionally, she sits on the Board Finance and Master Plan committees. Previously, she served as the school’s Middle School head and Upper School academic dean. Before LJCDS, Colleen was a founding member of Da Vinci Science and Design in Hawthorne and principal of Da Vinci Design. Earlier in her career, she was an English teacher and senior projects coordinator at the renowned High Tech High in Point Loma.

She holds a bachelor’s degree from the University of Maryland and a master’s degree from Middlebury College, both in English literature, with related study at Oxford and St. John’s. Colleen was also a Division I swimmer and runner. 

I want to express my heartfelt gratitude to our Search Committee co-chairs Marisol León ’03 and Trevor Bezdek ’95, as well as all committee members (listed below), for their dedication, wisdom and guidance. I would also like to thank everyone in our community who took part in the head of school search process; your participation and thoughtful feedback were invaluable. The warmth and passion of our community were palpable to all our finalists. We are excited for Colleen to lead this remarkable school for years to come. 

Please scroll down to read a letter from Colleen to the Crossroads community.
Juan Carrillo, P’21, P’23
Board Chair
Colleen O’Boyle

List of 3 items.

Our Next Head of School

A Message from Colleen O’Boyle
Nov. 2, 2021

Dear Crossroads Community, 

Over the years, I have visited many schools, some of which drew me in at first blush with excitement, curiosity, and wonder. Others left me wondering what if the school tended to the ecosystem where students learned, evolved, and thrived.

During the interview process, I asked for a tour of the Crossroads campus because I needed to feel the school—its hum, the pulse, and the stories that the walls and campus told. On that Saturday, as I meandered through the halls of the school sans children, I noticed an attention to students, their work, their voice, and the richness in diversity of being and thought. 

My tour guide, a phenomenal educator and leader, shared the vision of Crossroads as a place where students are at the center. It is an environment where students develop their personal commitment to learning, thinking, questioning, curiosity, and making a substantive and positive impact on a beautiful, diverse world. Yes, indeed, I thought. 

The finalist on-campus visit further illuminated the magic that is Crossroads. Students and teachers were eager, genuine, and joyful as they invited me into the art studios, science labs, classroom discussions, and nooks and crannies that created a beautiful, musical canvas called lunchtime. As I entered several classrooms, students greeted me with enthusiasm and pride about the work they were exploring and creating. I witnessed a community that places great emphasis on the relationships between students and educators. Here, students are inventors of their own theories, critics of other people’s thinking, analyzers of evidence, and composers or creators of their marks on the world.

While I have much to learn, I’ve gathered that Crossroads is a place that strives to provide students with anchors yet encourages them to think independently, engage in meaning-making and cognition, and advocate for what is right politically, ethically, and morally. This community lives its mission and fosters the full potential of each human being: the intellect and the imagination, the artist, the musician, the dramaturg and performer, the scientist and researcher, the athlete, the teammate, the captain, and the friend.

With immense gratitude and humility, I step into the head of school role in the 2022–23 academic year. I extend a special thank you to the Search Committee, whose love for and commitment to Crossroads was one of the many reasons I was so engaged in the search process. Over the coming months, I will partner with Bob, who has already demonstrated a deep commitment to this transition, and I look forward to getting to know each of you.



Head of School Search


List of 8 items.

  • Marisol León ’03

  • Trevor Bezdek ’95

  • Juan Carrillo

  • Ann Colburn

  • Bob Friedman

  • Erin Simon ’95

  • Bruce Stern

  • Lanhee Yung

Crossroads Leadership
Colleen will join a small but extraordinary group of Crossroads leaders. In 1971, Crossroads opened its doors to 34 middle schoolers, led by co-founder Rhoda Makoff. When she left the school in 1974, co-founder Paul Cummins became headmaster. He held that role until 1993, overseeing the expansion of Crossroads into a K-12 school. Roger Weaver, who had been Paul’s assistant head for a decade, was appointed the new headmaster. He stepped down in 2009, at which point his assistant head, Bob Riddle, was appointed under the new title “head of school.” Learn more about Crossroads School’s history here.