Independent School Moonshot Podcast

In this episode, Mattingly Messina, Founder of Throughline and Moonshot Lab Advisors, breaks down the potentially misaligned relationship between boards and fundraising in independent schools.Drawing from his experience as a trustee, former director of advancement, and consultant, he explains why the traditional board committee structure no longer serves schools and how it’s holding back strategic progress.Mattingly offers a fresh framework for embedding philanthropy across all board priorities, shares how heads of school can manage up with confidence, and challenges schools to stop apologizing for fundraising.If you’ve ever said, “My board doesn’t know how to fundraise,” this conversation is a must-listen.What You'll Learn from Mattingly Messina:Fundraising is a Board-Wide Responsibility: Advancement shouldn’t live in one siloed committee. Because funding affects everything, philanthropy must be embedded across all strategic focus areas.Shift from Function to Focus: Instead of organizing board committees around operational functions like finance or development, structure them around strategic priorities. This creates cross-functional collaboration and deeper trustee engagement.Stop Apologizing for Fundraising: Heads and leaders should confidently speak about fundraising. When it’s treated as essential and mission-driven, not uncomfortable or transactional, it changes how trustees show up.Manage Up with Courage and Strategy: Heads often try to fix advancement quietly behind the scenes. Real change happens when they name the dysfunction, invite the board into a new paradigm, and align with the board chair on a shared vision.Relationship Before Ask: Fundraising isn’t about the ask but the connection. When trustees speak authentically about why they believe in the school, that personal story is often more powerful than any solicitation.Discussion PromptsWhat assumptions do we hold about board members’ roles in fundraising, and where might those be outdated?How does our current board committee structure support or hinder our strategic goals?Where in our strategic plan is philanthropy required but not explicitly acknowledged?How can we better prepare trustees to be effective ambassadors rather than reluctant fundraisers?What’s one story a trustee could share that would inspire confidence and connection from a donor?

In this episode, John Farber, former head of school and current managing partner at RG175, shares hard-earned insights from conducting over 60 leadership searches.He dives deep into the evolving expectations for heads of school, especially the growing demand for business acumen and strategic thinking.From managing up to building strong board relationships and financial fluency, John explores what aspiring heads must understand to thrive. He also candidly reflects on why tenure has shortened and how boards can better support heads.This is essential listening for anyone exploring or supporting the headship path.What You'll Learn from John Farber:Business acumen is no longer optional. Heads must understand budgets, financial levers, and how to partner with their CFO and board.Managing up is a critical leadership skill. Strong board relationships enable heads to lead with confidence rather than fear.Most aspiring heads are underexposed to key responsibilities. Strategy, governance, and operational leadership are often learned on the job.Strategic clarity supports execution. When schools socialize their strategy and use it as a North Star, decisions are easier, and leadership alignment improves.Cultural fit is essential for success. Heads who align with the school’s culture have greater longevity and fulfillment.Discussion PromptsHow does your board currently assess business acumen during head or leadership searches?What support structures exist for new heads to develop their financial and operational fluency?How can your school better educate faculty and staff about the board’s expectations of the head?What would building a truly supportive board-head relationship at your school look like?How can you help aspiring leaders at your school get real exposure to board dynamics, finance, and governance?

Auxiliary programs can be a school’s hidden powerhouse if built with intention.In this episode of the Independent School Moonshot Podcast, St. Mark’s School’s Director of Operations, Kristi Jacobi, and Summer Programs and Auxiliary Revenue Collaborative's (SPARC) Senior Advisor, Bob Rojee, share how they transformed an empty summer campus into a dynamic, revenue-generating engine.You’ll hear how they aligned strategy with mission, managed culture shifts, and grew camp enrollment from 49 campers to over 1,000 sessions in just two summers.Whether starting an auxiliary from scratch or expanding what you have, their story offers invaluable lessons for any school leader ready to think iteratively and entrepreneurially.What You'll Learn from Kristi Jacobi and Bob Rojee:Prioritize with Purpose: Force-rank your goals before launching any auxiliary initiative to ensure strategic clarity and accountability.Invest in the Right Talent: Successful auxiliary programs need leaders who blend educational experience with business acumen.Market Demand Matters: Conduct thorough market analysis to uncover unmet demand, even in saturated markets.Be Mission-Adjacent: Programs must align with the school’s values while creating distinct experiences (e.g., brand-aligned but separate from full academic offerings)Manage Change Thoughtfully: Transparent communication and leadership endorsement are crucial to overcoming internal cultural resistance.Discussion PromptsHow clear are our priorities when it comes to generating non-tuition revenue?What hidden assets (space, expertise, brand) could we leverage better?Where might cultural resistance exist on our campus, and how can we thoughtfully address it?How could auxiliary programs enhance our school’s community relationships?Are we investing in the right talent to grow entrepreneurial programs?

Is your school's "system" running on intention or tradition? Jason Kern, Senior Innovation & Operations Strategist at Mission & Data, unpacks the role of systems in driving strategic execution across independent schools.Whether it's your strategic plan, enrollment, meetings, or sunset decisions, Jason shares why the path to progress starts with how we work, not just what we work on.This is a must-listen for school leaders ready to shift from reactive to strategic.What You'll Learn from Jason Kern:Start with Systems, Not Just Strategy: Strategy often fails in schools, not because of poor planning, but because there is no system to carry it through. A strong operational framework helps schools execute on priorities, not just talk about them.Operationalize, Don't Just Add: Schools excel at adding programs but struggle to retire outdated ones. Shift strategic initiatives into ongoing operations—or sunset them with clear rationale and community buy-in.Design Meetings with Purpose: A school's priorities show up in how it spends time. Redesign leadership meetings to focus on strategy, not status updates. Use consent agendas and dashboards to keep people informed outside the room.Adopt Agile Tools for Education: Tools like Scrum and School Operating Systems (SOS) offer proven ways to break big plans into manageable actions, bringing business discipline to school leadership.Use Data to Inform, Not Just Report: Systems aren't just about workflows—they're about insights. Jason urges schools to use data to drive decisions, not just to reflect on them after the fact.Discussion PromptsWhat systems in our school are implicit rather than intentionally designed?How do we know if our strategic plan is influencing day-to-day work?How do we currently transition initiatives from strategic to operational?Who is responsible for major priorities, and is that clear to everyone?What’s one recurring meeting we could redesign to be more effective?

You know that moment when it all clicks? When you finally understand how one decision leads to the next-why does a school that seemed stuck suddenly take off?That's this episode.David Lee, Head of Daycroft School, shares the story of how his team rebuilt trust, grew community, and nearly doubled enrollment (a 99% increase) in just five years.From personal touches in the admissions process to bold, calculated risks, this is a behind-the-scenes look at what it really takes to turn a school around.And the impact?Tuition now covers nearly all operating costs, freeing the school to grow auxiliary revenue and reinvest in facilities, benefits, and programs that make the community even stronger.This episode is a must-listen if you're trying to unlock sustainable growth.What You'll Learn from David Lee:Enrollment is everyone's job, but the head must lead. David joined every tour, followed up with families, and helped close enrollment conversations. His hands-on approach set the tone for success.Community creates Velcro. Focusing on building relationships between families, faculty, and students created a sticky environment where people wanted to stay.Hiring with purpose builds culture. Beyond credentials, David recruited educators with unique passions and a team-first mindset.Auxiliary programs are more than add-ons. Daycroft's summer camp and after-school enrichment generate 7% of annual revenue and extend the school's brand and culture.Bold decisions pay off. Opening during the pandemic and hiring ahead of enrollment were high-risk, high-reward moves that catalyzed growth.Discussion PromptsWhat is the head’s current role in the admissions process, and should that change?How might we create more “Velcro” between families at our school?What qualities do we prioritize when hiring teachers? Do we include community-building skills?Are we maximizing the potential of auxiliary programming?When was the last time we made a bold enrollment decision? What did we learn?

What makes teachers stay in your school?In this episode, Dr. Dennis Chapman shares the findings from his PhD dissertation, which explored teacher retention through the lens of servant leadership. Drawing on data from 2,000 independent school educators, Dennis reveals the seven leadership traits that matter most—and how school heads can lead with authenticity, trust, and purpose.At The Village School of Naples, where Dennis serves as Head of School, this approach isn’t just academic—it’s real. The school achieved a 97% teacher retention rate last year, underscoring how powerful values-driven leadership can be in practice.Whether you’re an aspiring leader or a seasoned head of school, this conversation will reshape how you think about faculty culture and retention.What You'll Learn from Dr. Dennis Chapman:Servant Leadership Matters – Teachers who feel seen, valued, and trusted by their head of school are significantly more likely to stay, regardless of compensation.The “7 C’s” of Retention – Communication, Culture of Appreciation, Compassion, Connection, Cultivating Trust, Compensation, and Coaching the Admin Team emerged as consistent themes among satisfied faculty.Compensation Is Not Always King – Teachers committed to their schools rated pay as less important, while those looking to leave ranked it highest.Authenticity Over Performance – Leaders who “perform” appreciation or visibility without sincerity risk damaging trust rather than building it.Early Feedback Prevents Surprises – Pulse surveys, transparent compensation models, and open conversations help reduce last-minute departures.Discussion PromptsWhich of the “7 C’s” of servant leadership—Communication, Culture of Appreciation, Compassion, Connection, Cultivating Trust, Compensation, and Coaching the Admin Team—are we currently strong in, and which ones need more focus?How does our current compensation structure support or hinder faculty retention?In what ways are we showing appreciation to our teachers consistently? Are those efforts meaningful and authentic?What systems do we have to gather honest faculty feedback, and how effectively are we acting on it?How transparent are we with our communication around key decisions? Where could we be more open or inclusive?How are we developing our division heads and admin team to embody servant leadership in their daily work?

What if your school's success depended on adopting a true growth mindset?In this episode of the Independent School Moonshot Podcast, Trace Urdan, Managing Director and education analyst at Tyton Partners, unpacks the sobering realities shaking up higher education and how independent schools can learn from them.Inspired by his Substack article "Surviving the Higher Ed Apocalypse," this conversation explores five growth models institutions can use to navigate demographic shifts, tuition pressures, and changing family expectations.Whether you're a head of school, board member, or aspiring leader, this episode offers practical insights for the road ahead.What You'll Learn from Trace Urdan:The Tuition Trap is Real: Schools that try to appear elite by raising prices often fall into a cycle of unsustainable discounting.Demographics Are Destiny: A declining population of affluent 18-year-olds is already reshaping education demand and independent schools are not immune.Differentiation is a Growth Strategy: Trace outlines five models (e.g., the Harvard, Juilliard, and Northeastern models) that schools can adopt to carve out a distinct niche.Shared Understanding Powers Change: The most crucial step school leaders can take is building a shared strategic view with their boards and leadership teams.Mission Can Fuel Growth: Schools can live their mission in new ways to unlock revenue if they're willing to break from tradition.Discussion PromptsWhat pressures from the higher ed world are already in our school?Which of the five models (Harvard, Juilliard, Northeastern, SNHU, Western Governors) feels closest to our current approach?How aligned are our board and leadership team on the core challenges we face?What new revenue streams allow us to live our mission in different ways?Are we pricing to reflect quality or pricing to stay competitive? What are the implications?What would it take for us to adopt a genuinely growth-oriented mindset?

What if your school’s strategy wasn’t just a plan—but a competitive advantage?This case study dives into a conversation with Tom Olverson, author of Leading Through Strategy: How Business Principles Can Help Independent Schools Thrive, who brings a fresh, business-minded lens to independent school leadership. More than an interview, it’s a roadmap for schools ready to move beyond imitation and build strategy around what makes them truly unique.Through real-world insights and lessons from Tom’s time as head of school and consultant, this episode offers a clear framework for defining your market position, aligning your team, and leading with purpose in a crowded and evolving landscape.What You'll Learn From Tom Olverson You:Strategic Differentiation: Dive into Tom Olverson's expert strategies for setting your school apart in a competitive landscape. Learn how you can propel your institution beyond the conventional, ensuring a unique position in the education market.Calculated Risks: Discover why embracing risks in your strategic plan is essential for breakthrough growth. Tom Olverson shares insights on stepping out of the comfort zone, advocating for strategies that challenge the status quo and spark innovation.External Insights: Learn the importance of incorporating external perspectives into your school's strategic planning. Olverson emphasizes how mentorship and outside expertise can offer fresh viewpoints, enhancing the depth and breadth of your strategic initiatives.Faculty Innovation: Understand the critical role of faculty in achieving strategic goals through innovation. Tom Olverson discusses creating supportive environments where educators can experiment and innovate, driving the school's strategic vision forward while fostering a culture of creativity and alignment.Discussion Prompts:What assumptions are baked into your current strategic plan? Where did they come from?How might your school’s mythology be preventing necessary change?Have you clearly defined the market segment in which your school is competing?How does your leadership team involve faculty in shaping and owning strategy?What risks are you taking or avoiding that could affect your school’s future?

How can independent school leaders embrace fundraising as a core leadership skill, even without formal training?In this episode, Jill Goodman, Jill Goodman Consulting, a consultant with decades of experience in independent schools and development strategy.Jill breaks down how school heads can shift their mindset around fundraising, build stronger donor relationships, and ensure that development is not an afterthought but an integral part of school leadership.Whether you’re a new head of school or a seasoned leader, this conversation offers actionable insights to strengthen your approach to development.What You'll Learn from Jill Goodman:Fundraising Requires a Leadership Mindset – Heads of school must embrace bravery and curiosity to engage with donors effectively rather than viewing fundraising as an intimidating task.The Power of Vision in Development – A compelling vision fuels fundraising success by aligning donor passion with the school’s strategic priorities.Heads & Development Directors Must Work Together – Development directors should have a seat at the leadership table, ideally reporting at board meetings to build trust and align donor strategies with institutional goals.Avoid the ‘Big Fish’ Trap – Schools often chase high-profile philanthropists rather than focusing on cultivating relationships with their most dedicated supporters.Donors Aren’t an ATM for Budget Shortfalls – Treating donors as a quick fix for financial gaps can damage long-term relationships. Instead, schools should diagnose and address the root cause of financial challenges.Discussion PromptsWhat are the most significant barriers that keep independent school leaders from embracing fundraising as part of their leadership role?How can school heads shift their mindset from fear to curiosity regarding donor relationships?Why is it essential for development directors to have a seat at the leadership table, and how can schools facilitate this?What are the risks of relying on donors to cover budget shortfalls rather than addressing systemic financial issues?How can schools better engage their existing donor base instead of chasing high-profile philanthropists?

What if the key to filling your school’s enrollment wasn’t just about more marketing but about truly understanding your market?In this episode, Annie Davis, Chief Product Officer at WeVideo, shares how independent schools can use market analysis to not only validate new programs but also uncover hidden opportunities for growth.What You'll Learn:Market Sizing is Critical: Before launching new programs or adjusting tuition, schools need to assess the true size of their potential market to avoid costly missteps.Research and Data Matter: Competitive analysis, demographic research, and surveys can provide invaluable insights into who might be interested in your school—and why.Value Proposition Clarity: Schools that understand and communicate their unique value are more likely to attract families that are a good fit.Embrace Authenticity: Schools that confidently own their identity can avoid trying to be everything to everyone, leading to stronger community alignment and better word-of-mouth marketing.Iterate and Refine Regularly: Market analysis is not a one-and-done task. Regularly revisiting and updating your market research ensures strategies stay relevant and practical.Discussion Prompts:How well do we understand the demographics and motivations of our current families?What tools and resources could we use to conduct competitive and market analysis in our area?Are we confidently and clearly communicating our school’s brand identity and value proposition to prospective families?Have we proactively tested and validated new ideas before investing time and resources?What small, strategic changes could we make to broaden our addressable market without diluting our brand?