He was the first openly gay and youngest-ever Executive Director of the Asian Pacific American Labor Alliance and Institute for Asian Pacific American Leadership and Advancement. Gregory was also the first openly gay Chair of the National Council of Asian Pacific Americans, co-founder of the diversity initiative Inclusv, and serves on the board of directors for United We Dream and Asian Mental Health Collective. He co-authored Asian Americans and Pacific Islanders (AAPIs) Behind Bars: Exposing the School to Prison to Deportation Pipeline, a first of its kind report on the impact of mass incarceration and mass criminalization in the AAPI community. Gregory was President of the United States Student Association (USSA), where he played an integral role in the passage of the Student Aid and Fiscal Responsibility Act and the Healthcare and Education Reconciliation Act.

Gregory is also a graduate of the Rockwood Leadership Institute, the Management Center's Managing to Change the World, the Midwest Academy’s Organizing for Social Change, Training for Change’s Training of Trainers, New Leaders Council-DC Fellowship, 202Creates Residency Program, Spitfire’s Executive Training Program, Center for Story-Based Strategy’s Advanced Training and re:power's Political Training Program. Washington D.C. Mayor Muriel Bowser appointed him to serve on the Board of Pharmacy and Commission on Asian and Pacific Islander Affairs after he served a two-year term on the Gay, Lesbian, Bisexual, and Transgender Advisory Committee under the leadership of Mayor Vince Gray. Gregory also co-founded the Washington Highlands Civic Association and served as its Vice President. He has been named one of Washington DC's most influential 40-and-under young leaders, one of the 30 Most Influential Asian Americans Under 30, 40 Influential Asian Americans in Washington, DC’s Inaugural Power 30 Under 30™ Award Recipients, a Capital Pride Hero, and the "Future of DC Politics". In his spare time, Gregory enjoys singing karaoke, choreographing dances, and trying new recipes.