The recipient of a bachelor's degree in African American studies from Bates College, Damion Frye subsequently earned a master’s degree in teaching from Brown University and began his career as an English teacher at Benjamin Banneker Charter School. From 2000 to 2009, Damion Frye served as a math and English teacher at New Jersey-area middle schools and high schools, during which time he also spent three years as an adjunct professor at New York University.

From 2009 to 2011, Damion Frye served as an adjunct professor at Montclair State University and middle school dean of students at The Equity Project Charter School, where he designed and implemented the school's Grade 5 language arts curriculum. He later worked as director of mathematics with District 79 New York City and special assistant to the assistant superintendent of Newark Public Schools.

Since 2016, Mr. Frye has served as principal of Seth Boyden Demonstration School in the South Orange Maplewood School District, where he manages budgeting functions, plans bi-weekly professional development sessions, and works with the Parent Teacher Organization to increase parent engagement. Supplementing his professional pursuits, he holds membership with the Association for Supervision and Curriculum Development and the New Jersey Principals and Supervisors Association.