Jeffery graduated from the University of Maryland in Princess Anne, Maryland earning his degree in Exercise Science with a clinical concentration. He was a member of the Richard A. Hinson Honors Program and of the National Society of Collegiate Scholars. While in college, he tutored young children, and decided on teaching as a career. In July 2020 Jeffery earned an M.A.T. in Education from Relay Graduate School. Jeffery began teaching at Link as a 5th grade teacher and currently serves as Math Interventionist and Upper House School Culture Leader.