What if your school could double its revenue in just four years, without veering from its core mission? In this episode, Amy Jolly, Head of School at Applewild, shares how her team leveraged existing resources on campus to spark financial sustainability and programmatic growth.

From launching a junior boarding program during the pandemic to expanding a preschool that more than tripled in size, Amy walks us through the bold (and often imperfect) steps that made it happen.

This is a masterclass in iterative leadership. Amy breaks down how she made decisions, engaged her board, adapted when things didn’t work, and always asked, “Does this generate the revenue we need to serve students better?”

Independent school leaders will find inspiration in her strategic clarity, her willingness to let go of legacy programs, and her unapologetic focus on mission-aligned sustainability.

What You'll Learn From Amy Jolly:

Iterative leadership fuels sustainable change. Amy didn’t wait for perfect answers — she tested ideas, learned from what didn’t work, and kept moving forward.
Revenue is a key indicator of viability. Every new program was evaluated based on its financial contribution to ensure mission-driven sustainability.
Growth came from optimizing existing strengths. Instead of adding flashy new initiatives, Amy doubled down on programs with untapped potential already on campus, like preschool and homestay.
Board alignment made bold moves possible. A nimble, trusting board allowed Amy to experiment, pivot, and act quickly when needed.
Letting go is part of progress. From cutting Latin to sunsetting underperforming campuses, Amy wasn’t afraid to say, “This isn’t working,” and reallocate resources strategically.

Recommended Next Steps:

Conduct a campus asset audit. Inventory what you already do well, from physical assets to niche programs, and explore ways to scale.
Create a pilot-to-scale decision framework. Follow Applewild’s lead: start small, evaluate impact, and scale what works.
Review underperforming programs. Use enrollment and revenue data to assess which programs no longer align with your mission or market.
Train your board on iterative strategy. Help trustees understand how adaptive strategy works and why not everything needs to be a home run on day one.
Reframe risk-taking in your culture. Encourage faculty and staff to view experimentation as part of continuous improvement, not a threat to tradition.

Doubling Applewild School’s Revenue in Four Years (2024)

Independent School Moonshot Podcast