Shifting Self and System

Courtney Winkfield is a veteran educator, executive coach, and racial equity leader with over twenty years experience leading at the school and district levels in public education systems. Winkfield has 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 NYC Department of Education. 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 Winkfield’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. 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.

Ruby Ababio-Fernandez is the executive vice president of programming and development at Courageous Conversation© and comes to the work with over twenty-three years of educational experience and an unyielding commitment to a vision of transforming lives of adults and children as well as transforming communities and school systems. Dr. Ababio-Fernandez served as associate vice president for equity and leadership development for the New York City Leadership Academy (NYCLA) before her transition to the role as deputy superintendent and senior executive officer of the Office of Equity and Access (OEA) for New York City’s Department of Education. Her extensive portfolio includes the citywide Implicit Bias Initiative, Advanced Placement for All, DREAM-Specialized High Schools Institute, as well as several youth development programs. Dr. Ababio-Fernandez’s leadership in confronting racial inequities helped forge new paths for developing the will, skill, knowledge, and dispositions needed to achieve educational equity for underrepresented and underserved students, families, and communities. As chief strategy officer of NYC’s Department of Education, Dr. Ababio-Fernandez directly supported the chancellor of schools in creating and managing a comprehensive and coherent vision for the agency and in developing effective leaders to advance racial equity. Dr. Ababio-Fernandez earned a bachelor’s degree in English from Framingham St. College, a master’s degree in curriculum and instruction with specialization in literacy from Lesley University, a master’s in educational leadership studies, and a doctorate in urban educational leadership from Teachers College, Columbia University. She currently resides in New York with her family.