Gregg is a national presenter on admission testing, college planning, and executive function. He brings 20 years in college counseling and admissions, with leadership roles at independent schools, university admissions at Northeastern and UMass Amherst, and nearly a decade reading applications for UCLA. He holds an M.Ed. from UMass Amherst and certificates from IE University and Harvard, and is a two-time UChicago Outstanding Educator award recipient.