John O’Brien comes to Oak Hill School with over thirty-five years of experience in the independent school world. Originally from Massachusetts, he completed his Bachelor of Arts in History at Trinity College in Connecticut and his Master of Arts in American Studies at Dartmouth College. He has taught students in Grades 5-12 and has been a coach of numerous interscholastic sports teams. John’s various administrative experiences have included serving as Assistant Dean of Admission at Phillips Andover Academy in Andover, MA, Head of Middle School, Head of Upper School, and Associate Head of School at Viewpoint School in Calabasas, CA, and Head of School at both Saddle River Day School in Saddle River, NJ, and at St. Mary’s School in Aliso Viejo, CA. During his years at St. Mary’s, the school’s programs and reputation were greatly enhanced, leading to significant growth in both enrollment and fundraising activities. He has also served as the chair of school accreditation teams for the California Association of Independent Schools (CAIS).

The Oregon lifestyle suits John well, as he is an avid runner, hiker, and golfer. He also has two grown sons, Jack and Chris, who reside in Southern California. One fun fact: He and his sons are citizens of both the United States and Ireland (John’s mother was born there).