A Tampa native, Gwendolyn Henderson was born on October 5, 1964, and grew up in the working-class Carver City neighborhood. She attended Roland Park Elementary, Morgan Woods Elementary, West Tampa Junior High School, and Pierce Junior High School. After graduating from Jefferson High School, she received her Bachelor of Science degree in education from Florida Agricultural and Mechanical University (FAMU) and received a Master of Education and Education Specialist degree in educational leadership and higher education administration from Saint Leo University. She is an accomplished and highly effective educator with Hillsborough County Public Schools and owner of Black English Bookstore.
Henderson is the proud daughter of the late Asbury Henderson, a Korean war veteran. She considers it an honor to be the primary caregiver for her 92-year-old mother, Gladys Austin Henderson. She has one favorite daughter, Ariel Amirah, a graduate of Jefferson High School and Howard University. Henderson is a 32-year resident and pioneer of the revitalized historic Tampa Heights neighborhood, which she purchased with the support of Tampa Preservation, Inc., and the Mayor Sandy Freedman's Challenge Fund.
She has been a member of Delta Sigma Theta since 1994, an international sorority dedicated to public service. For the school district, she serves as secretary on the Entrepreneurship in Education Advisory Board. She is a life member of the Florida A&M University Alumni Association, Saint Leo University Alumni Association, American Booksellers Association and Southern Indie Booksellers Alliance.
Additionally, she serves as chair of the Community Redevelopment Agency's board, as well as the Public Safety Coordinating Council and chairs the Parks, Recreation and Cultural Committee. She was appointed to serve as a board director on Hillsborough Area Regional Transit Authority (HART) by Mayor Castor.