Daileader attended St. Anthony's High School in Smithtown and then South Huntington, New York.
Daileader has also created numerous courses for The Teaching Company on topics including the Middle Ages, Crusades, and Charlemagne.
As a graduate student, Daileader was a four-time winner of the "Harvard University Certificate of Distinction in Teaching."
[1] Daileader also received the Thomas Ashley Graves Jr. Award for Sustained Teaching Excellence in 2016.
Daileader's book Saint Vincent Ferrier, His World and Life: Religion and Society in Late Medieval Europe won the La corónica International Book Award “for the best monograph published on Medieval Hispanic Languages, Literatures, and Cultures” in 2018.