Before joining the Fox School, he founded and ran his own theatre company. Philly Improv Theater was named to the Best of Philly list twice by Philadelphia Magazine, Gregory was named a “Creative Connector” by Leadership Philadelphia, and he testified before City Council on arts funding. In 2022, he handed day-to-day responsibilities for the business to a new management team.

Gregory received his master of public administration from the University of Pennsylvania while concurrently earning a bachelor of arts in history. He is also a member of several nonprofit boards including Leadership Philadelphia and Church of the Holy Trinity Rittenhouse Square (where he serves as co-chair). In his free time, Gregory enjoys leaving the city to be outdoors hiking and climbing—his most recent summit was Toubkal in Morocco’s Atlas Mountains.