In this episode, Hugh Jebson, Head of School at St. John’s Episcopal Parish Day School, shares how independent schools can approach leadership with strategic insight and strong business acumen while maintaining their educational mission.

He discusses the impact of perpetual enrollment, transparent tuition models, and competitive teacher compensation on long-term school success.

Whether you’re a head of school, board member, or aspiring leader, this conversation challenges conventional thinking and offers practical insights for navigating the changing landscape of independent schools.

What You'll Learn From Hugh Jebson:

• Schools Benefit from Business Thinking. Independent schools incorporating business strategies into their leadership approach can improve financial sustainability, operations, and long-term viability.
• Perpetual Enrollment Reduces Friction. By removing annual re-enrollment and shifting to an opt-out system, schools can simplify administration and provide families with a seamless experience.
• Comprehensive Tuition Creates Transparency. Rolling fees into one clear tuition cost eliminates hidden charges and builds trust with parents.
• The Loyalty Model is Changing. Parents are becoming more transactional in their school relationships—schools must demonstrate their value annually to retain families.
• Investing in Teachers Pays Off. Schools that pay teachers well, provide strong benefits, and offer professional growth see higher retention and stronger student outcomes.
• School Leaders Benefit from Business Acumen. Many school leaders don’t receive formal finance, marketing, or operations training—developing these skills can strengthen leadership effectiveness.

Discussion Prompts

• What business skills should our leadership team develop to improve decision-making?
• What are the biggest obstacles to integrating business strategies into our school culture, and how can we overcome them?
• How does our school currently approach enrollment and retention? Could a perpetual enrollment model be a good fit?
• Are we pricing tuition in a way that reflects our actual costs? Are hidden fees affecting parent trust?