Bob Riddle Senior Consultant

Bob is a Senior Consultant in our Search & Consulting Group.

Previous Experience

Most recently, Bob served as the Head of School at Crossroads School for Arts & Sciences from 2009 to 2022. Bob demonstrated a deep commitment to social equity and inclusion by inaugurating “The Equity & Justice Institute” at his school. During his tenure, he launched the ambitious $110 million “Worlds Unimagined Campaign,” raising more than $80 million before his departure.  Other achievements include an impressive diversification of the student body and leadership teams, significant augmentation of financial aid provisions, and expansive developments in academic and co-curricular support structures.

Prior to his position as Head of School, Bob held multiple leadership roles at Crossroads. He served as Assistant Headmaster/Dean of Faculty from 2003 to 2009, Upper School Director from 1999 to 2003, and Upper School Assistant Director and Academic Dean from 1995 to 1999. He started at Crossroads as a Middle School Math Teacher in 1984. Bob's educational journey began with teaching positions across several other institutions, including Bedford Junior High School (CT) and Haverford Junior High School (PA).

Beyond his roles in leadership and teaching, Bob has been consistently active in community and professional endeavors. His affiliations include being a Member of the CAIS Secondary Board of Standards, Chair of CAIS/WASC Accreditation Visiting Committees, and President of the Independent School Alliance for Minority Affairs Board, among others. His dedication to creating inclusive environments is evident in his involvement with the Gay, Lesbian & Straight Education Network of Los Angeles (GLSEN/LA), where he co-founded the West Coast chapter and coordinated its first conference. Bob was also the national conference coordinator for the Progressive Education Network when it was held in Los Angeles.

Education & Interests

Bob holds an M.A. in Educational Administration from Columbia University Teachers College where he was a Klingenstein fellow, a B.S. in Secondary Education (Mathematics), and a B.A. in Psychology from Penn State University, and has completed the Executive Leadership Program at Stanford University’s Graduate Business School.

Bob and his husband live in Santa Monica, California and when not enjoying life by the beach, they spend as much time traveling as possible, not only experiencing the natural beauty throughout California but also immersing themselves in other countries and cultures, all the while seeing old friends and meeting new ones.