Head of School Search

In February 2022, the Board of Trustees unanimously voted to appoint Mariama Richards as the interim head of school for the 2022-23 school year. This appointment followed the decision by Colleen O’Boyle, who had been named the next head of school in November, to decline the position due to unforeseen personal circumstances. Mariama 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
The below is an excerpt from the Feb. 7 communication to the Crossroads Community.

I’m thrilled to report that [the Board of Trustees] unanimously voted to appoint Mariama Richards as the interim head of school for the 2022-23 school year, and she has graciously and enthusiastically accepted the position.

Mariama joined Crossroads in 2020 as the associate head of school with more than 20 years of experience as an educator and administrator. As Bob’s partner, Mariama has demonstrated expertise, wisdom and warmth that have proven invaluable. Her many responsibilities include overseeing the School’s COVID-19 response; supporting faculty and staff development; and utilizing her background in diversity, equity and inclusion to develop curricular and community initiatives to help make Crossroads a more welcoming environment for all. 

When Bob first announced his upcoming retirement in April 2021, many in our community had hoped that Mariama would throw her hat in the ring. However, at that time, overseeing the COVID-19 response for a school of Crossroads’ size and complexity remained a tremendous undertaking. Given the focus required to manage the ever-changing County guidelines and necessary School protocols, and as she was still relatively new to Crossroads, Mariama made the decision not to apply, prioritizing the well-being of the School.

Ten months later, we are fortunately in a much safer and more stable place, and Mariama is fully immersed in the life of Crossroads. The Board is confident that Mariama is the best person to lead the School as we enter a new chapter, and she has the full trust and support of the senior leadership team.  
We are grateful for Mariama’s deep commitment to the School and its mission. Crossroads is truly fortunate to have a leader of her caliber at the helm for the next school year, providing vision and continuity for our School community.

Several months ago, the Board asked Bob if he would consider serving in a consulting role after his departure, and he agreed. In this capacity, Bob will primarily focus on fundraising efforts for the School’s capital campaign—particularly the development of the upcoming Performing Arts Center—and will be available to support Mariama as needed. 

Over the coming months, the senior leadership team will make additional staffing decisions, including appointing a new interim associate head of school for 2022-23. Bob and Mariama will continue to keep you updated throughout this process.

We hope you will join us in congratulating Mariama on her new role.
Juan Carrillo P’21, P’23
Chair, Board of Trustees
Mariama Richards

List of 1 items.

Our Next Head of School

A Message from Mariama
“It was an honor to be asked by the Board to step in, and I am thrilled to serve as interim head of school at Crossroads next year. Over the past year and a half, I have learned so much about and so much from this community. The students, families, faculty and staff—myself included—truly love this institution. The educational program is exceptional, and the founding principles are as alive as they were at our inception. I look forward to learning and leading alongside all of you next year.”

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
Mariama 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.