Born and raised in the San Francisco Bay Area, Michelle Helvey began her independent school journey from the very beginning as a preschool student when she attended Pinewood School in Los Altos through 8th Grade and then attended Castilleja School in Palo Alto for high school. Unlike other students, however, she had a front-row seat to school administration watching her grandmother, Pinewood School’s founder, Gwen Riches, give critical direction at her young growing school. Mrs. Helvey was fortunate to have the benefit of carefully watching a strong leader in action as early as grade school when her grandmother would routinely consult her on school matters, as her oldest granddaughter and trusted student. Mrs. Helvey went on to assist in summer programs and eventually teach kindergarten.

In addition to on-the-job training locally, Mrs. Helvey grew a love of the world when she was young ­­– at first through literature and then through travel, study, and eventually living abroad. As a high school student, she spent one summer traveling throughout Europe and then later at Brigham Young University, where she completed her bachelor’s degree in English Literature, she enjoyed the privilege of studying abroad in London, England, with travel throughout Europe and even extending to the Middle East. These opportunities early in life cemented in her the importance and value of experiential travel for students, which she has worked to foster at Oakwood, having led international student trips to places including China, Germany, Switzerland, France, England, Italy, and Greece.

Despite a life of international travel and out-of-state university study, Mrs. Helvey married her childhood friend and quite literally “the boy next door,” Ted Helvey, and while raising their three children, they founded Oakwood School together. Their children have all now married, and Mr. and Mrs. Helvey are the happy grandparents of eight grandchildren, who simply see them as “Grams and Pops.”

Family has always been at the center of Mrs. Helvey’s life, and she has carried this into her professional life by making Oakwood her family, too. Oakwood School is an extension of the ideals and values that she holds dear, and that’s why you’ll often hear her talk about Oakwood’s core tenets, especially as they apply to school culture, which she has now worked for decades to build.