Dawn Matera holds a BS in Psychology, an MS in Special Education, and a Doctorate in Educational Leadership. Upon completing a teacher training program and obtaining her Connecticut State Teaching Certification, she taught complex learners, for over a decade, at schools for students with learning issues, such as Eagle Hill and Winston Preparatory.

In 2008. Dr. Matera founded her first education company, A Way to Learn, which provides tutoring, executive function coaching, and test prep to students. Additionally, in 2013, she co-founded The Westport Day School, a Connecticut state-approved special education school for students in sixth through twelfth grades. Dr. Matera also serves on the board of directors of Higher Heights Youth Empowerment Program, Inc., which helps equip under-represented youth with skills and resources necessary for post-secondary education.