Administration
Cara Wynn,
Headmaster
Mrs. Wynn has a BS in Elementary Education from Liberty University and an MS in Educational Administration/ Leadership from Florida State University. Her former positions include Preschool Director, Elementary Principal, MS/HS Assistant Principal, and Parent Relations Director at area schools. She has been married to Roger Wynn, a Tallahassee native and they have two sons, a daughter-in-law, and a grandson who all live in Tallahassee. Mrs. Wynn and her family are active in a local church. She authored a children’s book, The Giraffe on the Moon.
Other Administration & Staff
Alecia Donaldson, Registrar
Ms. Donaldson has an Associate's degree in Human Services from Tallahassee Community College. She is working toward her Bachelor's degree in Social Work from Florida State University. Ms. Donaldson grew up in the area and loves Tallahassee. She has experience working as a Registrar in local Charter Schools. Ms. Donaldson has two children, Cason and Kennedy.
Hannah Pitts, Dean of Grammar School
Mrs. Pitts has a BA in Education from the University of North Florida. She has many years of experience in teaching. She has taught every grade in the grammar school. Mrs. Pitts is married to Coach Dan Pitts, our PE Teacher. Their two children attend Tallahassee Classical School. Mrs. Pitts has been at Tallahassee Classical since 2021.
Kelly Roberts, Business Manager
Ms. Roberts has a BA in Business Administration from Flagler College and Associate of Arts degree from Tallahassee Community College. She is a certified event and wedding planner.
She owned an event/wedding rental and planning business for more than 16 years. Ms. Roberts has one son that attends Tallahassee Classical School. She has been at Tallahassee Classical School since 2022.
Craig Hampton, Discipline Interventionist
Mr. Hampton has an Associate of Science degree in Recreational Management and Sports Fitness from Tallahassee Community College. He also has his Associates of Arts degree from Tallahassee Community College. Mr. Hampton has experience working as a Children's Pastor. He is married to his wife, Mattea Hampton. He has been at Tallahassee Classical since 2021
Valarie Reed, School Nurse
April Finney, Food Services Director
