Coach Winchester, formerly Coach Ellis, has been teaching at Williamsburg since January 2007. She has her Bachelor's of Mathematics and of Secondary Education, as well as a Master's degree of Education, all from University of the Cumberlands. She coaches varsity softball and works the scorers table for all home sporting events. Coach Winchester is currently the Vice President of the Williamsburg Education Association, one of the leaders of the Curriculum Committee, and one of two high school reps for the Digital Learning Committee.