The director of education policy studies at the American Enterprise Institute think tank (AEI), Hess is the author of many books, including Getting Education Right: A Conservative Vision for Improving Early Childhood, K–12, and College (Teachers College Press, 2024), which he co-authored with Michael Q. McShane, and A Search for Common Ground: Conversations About the Toughest Questions in K–12 Education (Teachers College Press, 2021), which he co-authored with Pedro A. Noguera.
In addition to his work in the realm of policy, he has taught high school and college.