Our Team
Courtney Winkfield

Courtney Winkfield

Executive Director, Programming & Development

Courtney Winkfield is the executive director of Programming & Development at Courageous Conversation© and has over twenty years experience leading at the school and district levels in public education systems. In her prior roles as Deputy Chief Strategy Advisor for the Chancellor’s Office and Senior Advisor for the Office of Equity & Access within the NYC Department of Education, Winkfield helped develop strategic initiatives and strategies to address long-standing racial, ethnic, and socioeconomic disparities and promote equity and excellence in education through policy and advocacy, both within and outside of the agency. From 2006 to 2016, Winkfield served as a founding teacher, assistant principal, and principal of the Academy for Young
Writers, a public secondary school in East New York, Brooklyn.

Under Courtney’s leadership as principal, Young Writers took significant steps toward expanding opportunities for young people, including increasing the number of AP courses offered, creating multiple STEM pathways for students of all abilities, developing a nationally recognized 6–12 Gender-Sexuality Alliance to empower and give voice to LGBTQ+ students, and establishing a student-led Restorative Justice program.

She holds a bachelor’s degree in English from Lewis & Clark College, a master’s degree in English education from CUNY Lehman College, and a master’s in educational leadership studies from CUNY Baruch College.

Courtney’s forthcoming book on equity leadership will be published by Corwin Press in
2023. She lives in South Orange, New Jersey, where she serves as a member of the
South Orange-Maplewood Board of Education, with her husband and two children.