Gertrude Webb’s compassion for struggling students led her to found programs for teaching both children and adults with learning disabilities. During her first year of teaching in the Boston Public School system, Webb became attuned to learning disabilities when a bright student was unable to translate his ideas into writing. She contacted experts and began her own exploration of dyslexia and other learning disabilities, continuing her pursuits even after she left teaching to raise her six children. After a twenty-year hiatus, Webb returned to education, teaching at Curry College and earning a doctorate from Boston College. She founded both the Massachusetts Association for Children with Disabilities and the Program for Advancement in Learning for adults. The learning center at Curry College was renamed the Gertrude M. Webb Learning Center in her honor. After her retirement from Curry College in 1993, she continued to lecture and train teachers around the world, and served as president of the Webb International Center for Dyslexia, an educational consulting organization founded by some of her former students.

Gertrude Webb was honored at the 2002 Women Who Dared event in Boston.