Dr. Bosley began his teaching career in Webster County, Kentucky, after earning a Bachelor of Music in Music Education. Over the years, he taught general and instrumental music at the elementary, middle, and high school levels. He later earned a Master of Music in Woodwind Performance, completed doctoral coursework toward a Doctor of Arts in Saxophone Performance, and earned a Doctor of Education (Ed.D.) in Educational Leadership from the University of the Cumberlands in 2025.​​​​‌‍​‍​‍‌‍‌​‍‌‍‍‌‌‍‌‌‍‍‌‌‍‍​‍​‍​‍‍​‍​‍‌‍‌​‌‍​‌‌‌​‌‍‌‍​‌‍‌‌​​‍‍‌‍​‌‍‌‍‌​‍​‍​‍​​‍​‍‌‍‍​‌​‍‌‍‌‌‌‍‌‍​‍​‍​‍‍​‍​‍‌‍‍​‌‌​‌‌​‌​​‌​​‍‍​‍​‍‌‍​‍‌‍​‌‌​‌‍‍‌‌​​‍‍‌‍​‌‌‍‌​‌‍‌‌‍‍‌‌‍‍​‍‍‌‍‌​‌‍​‌‌‌​‌‍‌‍​‌‍‌‌​​‍‍‌‍​‌‍‌‍‌​‍‌‍‌‌‌‍‌​‌‍‍‌‌‌​‌‍‌​‍​‍‌‍‍‌‌‌​‌‍‌‌‌‍‌‌‌‌‌​‌‍‌‌​​‌‍‌‌‌​​‍‌‍‌​​‌‌‌‍‍‍‌‍‍‌​‍‌‌​​​‌‌‍‌​‌‌‌​‌‍‌‍‌‍‍‌‌​‌‌‌‌​‌‍‌‌‌​‌‌‌​​‍‌​‍‌‌‌‍‍‌‌‍‌‌‌​‍‌‍‍‌‌‌​‌‍‌‌‌‍‌‌​​‍‌​​‌‌​​​‌‌‍‍‌‍‌‌‌​‍‌‌​‍​‍​‌‌‌​​​‌‌‌‌‌‍‌‍‌‍‍‌​‌​‍‌​‌‌​‌‌‌‍‍‌‍‌‌‍​‌​‌‍‌​‍‌‍‌‌‌‍‌​‌‍‍‌‌‌​​‍​‌‍‌‍‌‍‍‌‌‍‌‌‌‍​‌‍‌​‌‌​​‌‍​‌‌‌​‌‍‍​​‌‌‍​‍‌‍‍‌‌‍​‍​‍‌‌

In 2017, Dr. Bosley relocated to California and joined BASIS Independent Fremont (BIF) as a music SET, where he also taught drama. Following the pandemic, he transitioned into administration, first serving as Middle School Dean of Students at BASIS Independent Fremont Upper School. He went on to become one of the founding Student Affairs team members at BASIS Independent Silicon Valley Lower School and was selected as an inaugural participant in the Spring Education Group’s Leadership Academy. Most recently, he served as Director and Principal of Upper School at Stratford Fremont Osgood.

Throughout his 16-year career in education, Dr. Bosley has taught students from transitional kindergarten (TK) through college, consistently demonstrating a deep commitment to student growth, engagement, and success. “Seeing the growth and continued success of our BASIS Independent students gives me high hopes that the world will be a much brighter place,” he reflects. He is now proud to return to where his BASIS journey began, serving as Associate Head of Schools at BASIS Independent Fremont.

Outside of school, Dr. Bosley remains an active musician, performing with chamber groups, orchestras, and wind ensembles across the Bay Area. He is also an avid traveler and lifelong supporter of the arts.