In 1968 Bob Caine began his career in education in the Kentfield School District. During that time, he was a coach, a teacher, and a principal. He served as superintendent for 29 years before retiring in 2008. For the past four years he has chaired the committee responsible for developing the Anthology of Historical Reflections (currently on the KSD web site). More recently, he has led this committee in planning the Centennial Celebration, which will take place in 2014. This year he is the President of the Kentfield-Greenbrae Historical Society.