Over her 25-year career in the arts and higher education, Gregory has been a high-level, results-oriented fundraiser and administrator with extensive expertise in all aspects of development and nonprofit management. She has been part of the leadership team on campaigns ranging in size from $200,000 to $40 million for a wide variety of organizations. Gregory has been a team member of such arts organizations as the California Theatre Council, the Los Angeles Theater Center, Stamford Center for the Arts, StageWest (MA), Tennessee Repertory Theatre and Yale Repertory Theatre/Yale School of Drama. In Pittsburgh, she has worked at the Green Building Alliance and at Robert Morris University.