Crossroads News

Colleen O’Boyle Appointed Next Head of Crossroads School

Progressive educator and administrator will succeed Bob Riddle in July 2022.
After a unanimous vote by the School’s Board of Trustees, administrator and educator Colleen O’Boyle was chosen to succeed longtime head of school Bob Riddle when he steps down at the end of the 2021-22 school year. 

“[Colleen] 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,” noted Board Chair Juan Carrillo in his Nov. 2 announcement to the community. “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, supervising three division heads as well as the directors of arts, athletics and learning resources. 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. Colleen 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. You can find her full bio here.

In a letter that accompanied the announcement, Colleen shared, “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.”

In April 2021, Head of School Bob Riddle announced his plans to step down in July 2022 after 38 years of dedicated service to the School, 13 of them as head. The Board of Trustees retained the executive search firm RG175 and formed a Trustee Search Committee. After a competitive nationwide search, the Committee interviewed in September eight semifinalists vetted by RG175. The Committee then invited four finalists to spend 2 ½ days in October touring both campuses and meeting with students, parents, faculty and staff. The feedback from those who met with Colleen was overwhelmingly positive.

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. Roger stepped down in 2009 and assistant head Bob Riddle was appointed under the new title “head of school.”  Learn more about Crossroads School’s history here.

Over the coming months, the School will provide opportunities for the community to meet and get to know Colleen and her family. The School will also celebrate Bob Riddle and the remarkable legacy he will leave behind when his tenure comes to a close at the end of the school year. 

“Bob has been a devoted educator and administrator at Crossroads for nearly four decades and has overseen a period of tremendous growth and innovation,” noted Juan. “He will leave Crossroads in a position of strength and opportunity that Colleen will build upon as the new head of school.


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