Entrepreneurial Thinking for Independent School Leaders

What makes some schools thrive while others struggle to adapt? In this episode of the Independent School Moonshot podcast, I sit down with Dr. Brett Jacobsen, President of the Southern Association of Independent Schools (SAIS), to explore how independent school leaders can think like entrepreneurs—not in the Silicon Valley sense, but in a way that fosters innovation, adaptability, and long-term success.

Brett brings decades of experience as a head of school and now works with nearly 400 independent schools across SAIS. He shares how leaders can spot trends before they disrupt their schools, balance daily demands with long-term strategy, and build cultures that embrace change. We also dive into the power of small, strategic shifts, why defining a 10-year target is critical, and how creating a shared language around innovation can transform decision-making.

Whether you’re leading a school today or preparing for leadership in the future, this conversation will give you fresh ways to align vision with action—and create a school built to evolve.

What You'll Learn From Brett Jacobsen:

• Entrepreneurial Mindset as a Leadership Tool – Being an entrepreneur isn’t about disruption for disruption’s sake; it’s about recognizing opportunities, scanning for signals, and iterating in real time.
• Start with Optimization, Not Overhaul – The most successful school transformations don’t start with revolution; they begin with refining what’s already working.
• Common Language Builds Momentum – Creating shared vocabulary around strategy and innovation strengthens alignment between leadership, faculty, and boards.
• Strategy vs. Daily Demands – Leaders often struggle to balance immediate challenges with long-term goals. Productivity tools, middle management development, and clear priorities are essential.
• The Power of the 10-Year Target – Successful schools use long-range visioning to guide decision-making, measuring progress with clear benchmarks instead of rigid plans.
• Cultivating Leadership at All Levels – Schools that act as “leadership factories” empower middle management, expanding strategic capacity across the organization.

Discussion Prompts

• What signals do we see in independent school education that could shape our school’s future? How are we responding to them?
• Are we balancing strategy with daily demands effectively? Where do we need better systems?
• How does our school define entrepreneurial thinking? Are we fostering a culture that encourages problem-solving and iteration?
• What is our 10-year target? Does our current strategic approach align with that vision?
• What small optimizations could we implement now that would have a compounding effect over time?