Our Blog » Virginia Chance School Welcomes Stephanie Medcalfe, Head of School

Virginia Chance School Welcomes Stephanie Medcalfe, Head of School

Families in the neighborhoods surrounding Virginia Chance School understand the value of place. They choose homes among mature trees, winding roads, and natural beauty because they know the environment matters. It shapes how children move, what they notice, how they feel, and how they come to understand the world around them.

Just beyond those wooded lanes sits a school built on the same belief- with a powerful academic purpose at its center.

 
Virginia Chance School has long offered children a distinctive beginning: a preschool through fifth-grade education where strong academics, purposeful relationships, nature-rich learning, and a deep respect for childhood work together. On its historic Glenview campus, children are known well, challenged with intention, and given the foundation to become curious thinkers, confident communicators, and resilient young leaders.


This year, Chance begins an exciting new chapter with the arrival of Stephanie Medcalfe as Head of School. Stephanie brings more than 30 years of experience in education and a career shaped by the belief that children learn best when they are both deeply known and meaningfully challenged.


Stephanie’s own foundation in progressive education was shaped during her years at The Orchard School in Indianapolis, a school rooted in experiential, hands-on learning on a 43-acre wooded campus. That experience helped form her belief that purposeful, developmentally responsive education cultivates curiosity, resilience, and joy. It also made her connection to Chance immediate and meaningful.

“What drew me to Chance was the clarity of its mission and the strength of its community,” Stephanie shares. “This is a school that understands childhood as a time of extraordinary intellectual, social, and emotional growth. Children are capable of deep thinking, complex problem-solving, and meaningful leadership when the learning environment is designed with care.”

Most recently, Stephanie served as Assistant Head of School for Academics and Lower School Director at Cape Fear Academy in Wilmington, North Carolina, a college-preparatory PreK–12 school. There, she led work in curriculum alignment, early literacy support, learning support, diversity and belonging, auxiliary programming, and scholarship initiatives. Her leadership contributed to enrollment growth and strengthened the academic experience across divisions.
 
Before 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 students to thrive academically, socially, and ethically.
 

That combination of experiences gives Stephanie a unique perspective on the power of Chance’s preschool through fifth grade model.

 
At Chance, the foundational years are not treated as a warm-up for “real school.” They are understood as the years when children form the habits that shape everything that follows: how they think, how they communicate, how they lead, how they collaborate, and how they respond when learning becomes challenging.


The learning at Chance is joyful, but it is not casual. Children are asked to explain their reasoning, revise their ideas, ask stronger questions, listen carefully, solve complex problems, and take increasing ownership of their work. Teachers know how to stretch advanced thinkers, support developing skills, and build classroom cultures where curiosity becomes intellectual courage.


This is what makes Chance distinctive.

Rather than asking young children to fit into a larger institutional system, the school is designed entirely around the needs and potential of children in the preschool through elementary years. Every classroom, every outdoor learning space, every relationship, and every learning experience is built for this stage of childhood — a stage that deserves both tenderness and high expectations.


For families who have historically looked first to K–12 or parochial schools, Chance offers a compelling alternative: a rigorous, research-informed, nature-rich elementary experience that prepares children exceptionally well for what comes next. Chance graduates leave with academic readiness, strong communication skills, self knowledge, and the resilience to step into new communities as capable, thoughtful leaders.


As Stephanie begins her leadership, Virginia Chance School is speaking with renewed clarity about what its families have long known to be true. A childhood rooted in curiosity, confidence, and resilience is not separate from academic excellence. It is one of the strongest foundations for it.

Stephanie brings both warmth and strategic vision to this next chapter. She holds a Master’s degree in Educational Leadership and an MBA from the University of North Carolina at Chapel Hill’s Kenan-Flagler Business School, preparation that reflects her commitment to both educational depth and thoughtful institutional leadership. Known as a collaborative and relational leader, she brings clarity, empathy, and high expectations to every community she serves.
 
She also brings a deeply personal understanding of family, community, and belonging. Raised in rural Indiana as the youngest of three sisters, Stephanie developed a lifelong commitment to equity, belonging, and courageous dialogue. She and her husband, Chad, have been married for more than 30 years and are the proud parents of two children. Their home also includes three cats. Outside of school, Stephanie enjoys reading, crocheting, watercolor painting, and volunteering in her community.


When asked what inspires her work, Stephanie returns to the same idea: children deserve schools that see them fully and challenge them well. They deserve places where their minds are stretched, their voices matter, and their sense of wonder becomes the foundation for disciplined, confident thinking.


That is the heart of Virginia Chance School.


To the surrounding neighborhood and broader Louisville community, Stephanie’s message is one of invitation: come see what childhood can look like when it is built with intention. Come see a school where academic challenge, natural beauty, strong relationships, and joyful learning come together. Come see how curiosity grows, confidence builds, and resilience lasts.
 
Virginia Chance School is proud to welcome Stephanie Medcalfe and excited to share this next chapter with the community.