Independent School Moonshot Podcast

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 PromptsWhat 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?

Note: This episode was originally an Expert Lab Coaching session inside Moonshot Lab, a membership community designed to help independent school leaders tackle complex business challenges in real-time.I’m making it available as a podcast episode to give you a feel for the kind of strategic conversations and problem-solving we do inside the Lab.In this session, Dana Nelson-Isaacs, Founder and President of DNI Consulting, helps school leaders crack the code on enrollment challenges by identifying whether the root cause lies in:Market dynamics (changing demographics, competition, economic factors)Marketing missteps (messaging, outreach, positioning, and lead generation)Getting this diagnosis right is critical—because a market challenge requires a different strategy than a marketing fix. Tune in to learn how to assess your school’s situation and ensure you’re solving the right problem.What You'll Learn From Dana Nelson-Isaacs:Market vs. Marketing Challenge Framework: Schools must determine whether their enrollment difficulties stem from external market shifts (demographic trends, economic changes, psychographic shifts) or internal marketing inefficiencies (outdated messaging, poor ROI on campaigns).Data-Driven Decision Making: Rather than making assumptions, schools should rely on demographic reports, psychographic research, surveys, focus groups, and marketing ROI analysis to assess their challenges.The Importance of Psychographics: Beyond demographics, schools should analyze how families make decisions, what they value, and how messaging should align with their priorities.Scorecards for Leadership: Schools should track enrollment funnel trends, marketing effectiveness, competitive landscape, and internal satisfaction to ensure alignment between school strategy and market realities.Change is Hard But Necessary: Schools in competitive or declining markets may need structural changes (new grade levels, different program delivery models). At the same time, those with marketing problems should focus on messaging, targeting, and outreach improvements.Discussion PromptsHow do we assess whether our enrollment challenges are due to marketing weaknesses or broader market trends?What data do we already have (or need) to make informed strategic decisions about our enrollment strategy?How well does our current messaging align with what prospective families are looking for? Where are the gaps?What are some out-of-the-box marketing tactics we haven’t explored that could make a difference?What would be the most feasible shift if we had to change something structurally about our school to improve enrollment?

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 PromptsWhat 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?

From streamlining operations with tools like ChatGPT and Gemini to reducing teacher burnout, this episode dives into AI's practical and strategic uses in independent school operations.Christina Lewellen, Executive Director of the Association of Technology Leaders in Independent Schools (ATLIS), shares insights on adopting AI thoughtfully, protecting privacy, and preparing schools for a rapidly evolving future.Whether you're curious about the latest AI tools or looking to build flexible policies for your workforce, this conversation offers actionable takeaways to enhance productivity and achieve your school's goals.What You'll Learn From Christina Lewellen:Generative AI as a Gateway: Tools like ChatGPT can simplify processes like email drafting and initial brainstorming, offering an easy entry point to AI for schools.Specialized Productivity Tools: Platforms like Gemini and Scribe provide targeted applications for email summarization, data analysis, and creating operational guides, demonstrating AI's operational value.Security and Privacy Concerns: Schools must exercise caution when data is uploaded into AI tools to protect privacy and intellectual property.AI's Long-Term Impact: Current AI tools resemble the "dial-up phase" of the internet, with rapid evolution expected. Schools should focus on building flexible, adaptable policies.Combating Burnout: AI has the potential to alleviate teacher workload by automating administrative tasks, freeing educators to focus on students.Discussion PromptsExploring AI Tools: What AI tools, like ChatGPT or Gemini, could our school adopt to streamline operations, and how can we encourage experimentation safely and productively?Privacy and Data Security: How can we ensure that our use of AI tools protects sensitive data and aligns with best practices for privacy and security?Reducing Burnout: What specific administrative tasks or processes could we automate with AI to help reduce teacher workload and improve efficiency?AI in Strategic Planning: How can we integrate AI into our school's long-term strategy and philosophy to better prepare students and staff for future scenarios?Professional Development: What training or resources should we prioritize to help our staff effectively use AI tools and remain critical, informed users of emerging technologies?

Kevin Fullen, Head of School at Providence Country Day School, shares his remarkable journey in transforming the school’s enrollment from 200 to 375 students in just four years. He discusses their bold tuition reset and innovative strategies, including launching a global online academy and merging with a nearby laboratory school. The conversation dives into navigating COVID-19 challenges, fostering community ties, and embracing change. Fullen emphasizes the importance of adaptability in leadership and the courage to innovate in education, offering valuable insights for school leaders.

Deans are the unsung heroes of independent schools, often shaping culture, managing crises, and fostering connections with every constituency on campus.In this episode, Bridget Johnson, founder of the Dean’s Roundtable, shares her expertise on the critical role of deans and why their work is essential to a school’s success.From creating positive cultures to navigating the emotional labor of student life, Bridget offers actionable advice for school leaders to support their deans better.Whether you’re a head of school, an aspiring leader, or simply curious about the work of student life professionals, this episode will give you a fresh perspective on their invaluable contributions.What You'll Learn From Bridget Johnson:Deans as Cultural Architects: Deans are the cultural architects of a school, shaping the tone and values that influence the community.The Importance of Regular Check-Ins: Regular communication and debriefing check-ins with the head of school are essential to ensuring deans' success and preventing burnout.Impact on Enrollment and Retention: A strong dean-student relationship contributes directly to enrollment, retention, and alumni satisfaction.Investing in Professional Development: Schools must invest in professional development, including leadership, crisis management, and restorative practices, to empower deans.Proactive Culture-Building: Proactive culture-building at the start of the year helps defuse conflicts before they arise.Culture Drives Messaging: A strong school culture, grounded in shared values and mission, supports alignment in crisis and non-crisis moments.Discussion PromptsRecognizing Emotional Labor: How can we better identify and support the emotional labor and challenges facing our dean of students?Integrating Deans into Leadership: What steps can we take to ensure deans are part of our leadership discussions and decision-making processes?The Power of Culture-Building: How can proactive culture-building at the start of the school year reduce conflicts and crises later?Aligning Mission and Student Life: How can we align the work of the dean’s office with our school’s mission, values, and enrollment goals?Investing in Growth: What professional development opportunities could we offer our dean and student life team to help them thrive?

How can schools build trust and alignment to weather any storm? In this episode, Scott Allenby, Chief Strategy and Communications Officer at Proctor Academy, dives into the critical connections between strategy, communication, and culture.He reveals how identifying “immovables”—the non-negotiable core elements of a school’s identity—can guide crisis responses and daily operations.From fostering trust among stakeholders to crafting authentic messaging, Scott shares actionable insights to help school leaders strengthen their communication practices and align their teams for long-term success.Whether preparing for the unexpected or looking to refine your strategy, this episode offers a wealth of practical takeaways.What You'll Learn From Scott Allenby:Preparation Is Key: The groundwork for effective crisis communication lies in pre-established trust and alignment among stakeholders.Authenticity Matters: Crisis messaging must reflect the school’s authentic voice and align with its mission to maintain credibility.Immovables Define Identity: Identifying and understanding a school’s non-negotiable core values (“immovables”) provides a foundation for consistent messaging and strategic decision-making.Trust Capital: Consistently authentic communication builds “trust capital” over time, crucial for weathering crises.Proactive Relationships: Regular interactions between the head of school, board, and communication teams are essential for maintaining alignment and trust.Culture Drives Messaging: A strong school culture, grounded in shared values and mission, supports alignment in crisis and non-crisis moments.Discussion PromptsPre-Crisis Preparation: How aligned is our leadership team regarding our school’s mission and values? What proactive steps can we take to strengthen trust and communication among our leadership team and the board?Crisis Response Planning: Are our roles clearly defined during a crisis? Who is responsible for key communication tasks? Do we have redundancies to ensure crisis messaging can go out smoothly even if a key team member is unavailable?Building Trust Capital: Are our current communication strategies fostering trust with stakeholders? How can we improve? How do we balance vulnerability and professionalism in our messaging to maintain authenticity?Identifying Core Values: What are our school’s “immovables”? If one of these were to change, would our school lose its identity? How can we ensure these immovables are consistently communicated to our community?

In this episode, David Sullivan, Senior Advisor at the Summer Programs and Auxiliary Revenue Collaborative (SPARC) and former Head of School at Breakwater School in Portland, Maine, reveals how he transformed a $350,000 deficit into consistent surpluses.Through innovative auxiliary revenue strategies and bold leadership, David shares actionable insights for independent schools looking to achieve financial sustainability and unlock new growth opportunities.What You'll Learn:Leadership Change and Financial Opportunities: When David Sullivan took over as head of Breakwater School, he faced a $350,000 deficit on a $2.5 million budget. This challenge spurred him to innovate, leading to a strategic focus on auxiliary revenue that would ultimately transform the school’s financial health.Auxiliary Revenue as a Lifeline: Sullivan’s background in auxiliary programs and the school’s financial situation led him to develop innovative auxiliary revenue streams. Incorporating these streams with traditional fundraising and enrollment strategies provided financial stability for the school.Living Endowment Concept: A major donor advised Sullivan to view auxiliary programs as a living endowment. Instead of relying on large donations to build an endowment, generating consistent revenue through auxiliary programs provided a sustainable financial model.Initial Investments and Growth: Breakwater School initially faced financial losses in its auxiliary programs, but within two years, the programs began to break even and eventually grew by 20% annually. Over time, these programs contributed significantly to the school’s financial health, increasing their budget contribution from less than 3% to 25%.Community Integration and Public Purpose: By developing programs for public school students, Sullivan fostered community goodwill and enhanced the school’s public purpose. This integration helped rebrand the school as a community resource rather than an isolated institution.Discussion Prompts:Mission Alignment: How can we ensure our auxiliary programs align with and enhance our school’s mission and educational philosophy, creating a cohesive and consistent experience for all students?Strategic Priorities: What strategic priorities should guide the development of our auxiliary programs, and how can they support our long-term goals and financial stability?Community Engagement: How can we use auxiliary programs to strengthen our ties with the local community and serve a broader population, enhancing our school’s public image and outreach?Leadership and Investment: What investments in leadership and resources are necessary to successfully expand and manage our auxiliary programs and ensure their positive contribution to our school’s overall operation?Operational Challenges: What operational changes or innovations are required to support the growth of our auxiliary programs, and how can we address potential challenges related to facilities, staffing, and communication?

Discover how strategic leadership, data-driven insights, and collaborative governance can reimagine longstanding programs in schools. Join Autumn Graves, Head of School at St. Anne’s-Belfield School, and Ari Betof, Co-Founder & Partner of Mission & Data, as they share actionable strategies to drive meaningful change.What You'll Learn:Strategic Evaluation Techniques: Learn how to assess core programs against your school's mission and identity, ensuring they remain relevant and impactful in an ever-changing educational landscape.Engaging Governance: Discover effective strategies for involving your board in critical discussions, enhancing their understanding and support of necessary institutional changes.The Power of External Insights: Understand the value external consultants can bring to your strategic planning, offering fresh perspectives and data-driven analyses to guide your decisions.Mission-Driven, Data-Informed Decisions: See how balancing quantitative data with your school's mission can lead to more nuanced and effective strategic decisions.Discussion Prompts:Identifying Core Programs and Values: How do we determine which programs or aspects of our school are core to our identity and mission? Reflect on a process to evaluate whether a program is immovable, essential, or exceptional to the school's identity.Engaging the Board in Strategic Decisions: What strategies can we use to effectively engage our board in discussions about significant institutional changes or evaluations? Discuss how to present data and strategic considerations to the board to facilitate informed decision-making.The Role of External Consultants: Under what circumstances should we consider bringing in external consultants to assist with school projects or evaluations? Debate the benefits and challenges of external consultation, including potential impacts on data analysis, strategic planning, and professional development.Balancing Data-Driven Decisions with Mission Alignment: How do we ensure that our decision-making process remains data-informed and mission-driven? Share methods for integrating qualitative and quantitative data in strategic planning and decision-making.Long-Term Tracking and Evaluation of Strategic Initiatives: What mechanisms can we implement to track the success of reimagined or newly invested programs? Discuss establishing metrics for success and periodic reviews to assess the alignment and impact of strategic initiatives on the school's mission and goals.

How can schools save time, reduce overwhelm, and achieve better outcomes with the right external partnerships? Chris Pryor, founder of Lead Team Partners and School Partner Connect, shares the answer in this episode.As school leaders juggle daily demands and big-picture priorities, Chris shares why outsourcing is more critical than ever—and how to find the right partner to move your initiatives forward.Tune in for actionable strategies to streamline the process and unlock new possibilities for your school.What You'll Learn From Chris Pryor:Clarify the Problem First: Before seeking external partners, school leaders must clearly define the problem, goals, budget, and internal resources needed.Outsourcing Saves Time, When Done Right: Finding external partners can reduce workload and increase efficiency, especially for initiatives that demand specific expertise.Avoid Local Bias: Schools often default to nearby providers but miss valuable talent. A national or global search can uncover high-quality partners.Alignment and Preparation Are Key: Successful partnerships require internal buy-in, thoughtful preparation, and a shared understanding of the project scope.Measure Twice, Cut Once: Develop a rubric to objectively evaluate external partners and encourage healthy discussion when narrowing down options.Discussion PromptsClarify the Problem: Are we clear on the problem we are trying to solve with our current or future projects? How can we ensure alignment across our team before engaging external partners?Evaluate Outsourcing Opportunities: What current initiatives could benefit from external expertise or support? Are there tasks we’re handling internally that external partners would more efficiently manage?Rethink Partner Selection: Do we default to local providers, and could broadening our search lead to better options? How can we diversify the types of external experts we consider?Align Internal Resources: How can we better prepare internally to support successful partnerships? What steps can we take to align internal stakeholders before initiating a project?Plan for Long-Term Impact: How might outsourcing help us tackle big-picture priorities more effectively? What systems or tools could we implement to improve how we manage external partnerships in the future?