Winfield returns to Boston Public Schools following a MSW from Simmons College and having spent several years working with at-risk and disadvantaged urban youth in both New York City and the District of Columbia. In these settings, he worked extensively as a Career Counselor, Student Tutor and Youth Mentor. In addition to his counseling and experience in education, Winfield also has a business and entrepreneurial background having founded and operated businesses in New York City and Maryland. While in the role of Coordinator of School Culture he plans enhance student, staff and parent engagement, working with the belief that every child can achieve academic success and maximize their potential.