Stephanie Medcalfe

 

Stephanie brings more than 30 years of experience in education. She is grounded in the progressive values she developed during her formative years at Indianapolis’s The Orchard School, a fellow member of the Progressive Education Network. She holds dual graduate degrees in educational leadership and business administration, a combination that reflects both her depth as an educator and her readiness to lead with strategic vision. Stephanie believes strong leadership begins with knowing students, supporting teachers, and designing learning experiences that prepare young people for meaningful lives.

 

She is drawn to VCS precisely because she recognizes in our community the same commitment to cultivating curiosity, resilience, and joy that has guided her career. Her more recent experience at a college-preparatory pre-K – 12th-grade school further reinforced her conviction that progressive, student-centered education prepares children to thrive academically, socially, and ethically; we know that to be true, as we have seen generations of Chance graduates flourish throughout their secondary education and into college and adulthood.

 

Stephanie currently serves as Assistant Head of School for Academics and Lower School Director at Cape Fear Academy in Wilmington, North Carolina. Grounded in the classroom and guided by mission, Stephanie oversees the Lower School while also leading initiatives in diversity, equity, and inclusion, learning support, and auxiliary programming across the PreK–12 campus. Her leadership has contributed to enrollment growth, curriculum alignment across divisions, expanded early literacy interventions, and scholarship initiatives that have increased socioeconomic diversity. Known as a collaborative and relational leader, Stephanie brings clarity, empathy, and high expectations to every community she serves.

Stephanie’s longest teaching tenure was at The Orchard School in Indianapolis, a progressive school rooted in experiential, hands-on learning. Its 43-acre wooded campus brought the school’s promise of Nature as Teacher to life, shaping Stephanie’s belief that purposeful, developmentally responsive education cultivates curiosity, resilience, and joy.

Before joining Cape Fear Academy, Stephanie served as Assistant High School Principal at Brebeuf Jesuit Preparatory School in Indianapolis, where her work in a mission-driven, college-preparatory environment reinforced her belief that progressive, student-centered education prepares adolescents to thrive academically, socially, and ethically.

Stephanie holds a Master’s degree in Educational Leadership and recently completed her MBA at the University of North Carolina at Chapel Hill’s Kenan-Flagler Business School. Her combined preparation in education and business informs a thoughtful, strategic, and mission-centered approach to leadership.

Raised in rural Indiana, Stephanie developed a lifelong commitment to equity, belonging, and courageous dialogue. She began her teaching career in New Albany and Borden, Indiana, and fondly remembers welcoming her first child just hours before Thunder Over Louisville — sharing pizza and fireworks with the nursing staff from her hospital room.

Stephanie was raised in the Quaker faith, the youngest of three sisters, and has been married for over thirty years. She and her husband, Chad, are the proud parents of two children and would be empty nesters if not for the dog and three cats. She enjoys reading, crocheting, watercolor painting, and volunteering in her local community.