Gregg grew up in Northeast Kansas and attended Kansas State University where he received his initial teaching degree. He first started teaching in Nebraska in 1995 with Pawnee City Public Schools. As technology grew, Gregg became the director of technology for Pawnee City. In 2004, Gregg had the opportunity to join the ESU 4 team as the director of technology. He obtained a Master of Education degree from Lesley University in 2005.
Gregg became the fourth administrator for ESU 4 in 2017 and obtained his administrative degree from UNK in 2018.