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Regina Gwynn has a diverse work experience spanning various industries. Regina is currently a Co-Founder of Black Women Talk Tech since 2017. In 2021, they took on the role of VC-in-Residence at Pipeline Angels, where they help provide funding and support for underrepresented founders. Regina also joined Ada Ventures as a Scout in 2021, focusing on investing in breakthrough ideas in climate, economic empowerment, and healthcare & aging. Prior to these roles, Regina was the Co-Founder & CEO of TresseNoire, a beauty booking platform catering to women with textured hair. Regina has also worked in marketing at The Apparel Group, served as a Consultant at Monitor Group, and held various marketing positions at Macy's Merchandising Group.

Regina Gwynn earned their Bachelor of Science degree in Marketing from Rutgers University, where they studied from 1998 to 2001. In 1996 to 1997, they attended the Fashion Institute of Technology and obtained a degree in Fashion Buying and Merchandising. Regina further pursued their education and completed an MBA degree with a focus on Marketing, Entrepreneurship, and Strategy from Northwestern University's Kellogg School of Management between 2007 to 2009. Alongside their formal education, Regina Gwynn also obtained a certification from the Black Venture Institute, offered by the UC Berkeley Executive Education, in April 2021.