Independent School Moonshot Podcast

Peter Baron

Curious about the latest trends and breakthroughs in independent schools reimagining the business model? The Independent School Moonshot Podcast, packed with real-world examples, is just what you need!

  1. 1d ago

    Why Advancement Talent Is Hard to Find, and Where to Look Next

    Heads across the country are noticing the same thing: it is getting harder to find strong advancement people. Jill Goodman of Jill Goodman Consulting returns to the podcast to help us understand why and what schools can do about it. Jill has spent nearly 30 years in and around schools as a parent volunteer, trustee, and administrator before founding her consulting practice in 2017, and she now works with development offices and heads of school nationwide. Her starting point is honest and practical. Schools want deep experience from higher ed, nonprofits, or other independent schools. Still, the role at a small or mid-sized school is broader and less defined than at a traditional nonprofit, often a one- or two-person shop carrying a long list of assigned duties. Candidates who have specialized in one area, such as annual fund or alumni relations, can look at that scope and reasonably wonder whether it is realistic. From there, Jill opens up the opportunity side of the picture. Schools offer real advantages, including tuition remission, a fundraising goal that is a modest share of the operating budget, and the daily lift of being around curious, healthy kids and teachers who care. She makes a strong case for nontraditional hires, describing the background and qualities she looks for, from corporate sales and entrepreneurial instincts to comfort around wealth and a healthy relationship with hearing no. She is equally clear about what success requires from the school: enough hours to do the job, a mentoring budget, a head comfortable in their fundraising role, and a board that understands advancement as a core part of the financial plan. In the extended conversation for Moonshot Lab members, Jill lays out what a new advancement director should accomplish in years one, two, and three, and when fractional support makes sense. Top 5 TakeawaysThe small-school advancement role demands breadth, and that changes who will say yes. A candidate coming from a large school or nonprofit has often specialized in one function. At a small school, one person handles everything from events to the database to major gifts, usually alongside duties outside development. Jill advises heads to name the real priorities clearly and offer support so the role reads as a focused opportunity rather than an open-ended list.Nontraditional candidates can be a strong source of advancement talent. Jill looks for corporate sales experience, an entrepreneurial spirit, project management skills, tech fluency, and a genuine connection to the school as a parent, alum, or faculty member. She also looks for something harder to interview for: comfort with wealth and power, and a personality that makes people pick up the phone. Many of these qualities are easier to see in person than over Zoom.Hearing no is part of the work, and it is useful information. Jill reframes rejection as feedback. A no might mean the ask came too early, the room was misread, or the gift needs to be shaped differently. People comfortable with that tend to grow quickly in the role, while those who fear it struggle to move relationships forward.Hiring a great person for too few hours sets everyone up to fall short. Jill describes schools that hire for fifteen hours a week and then require five hours of internal meetings, leaving ten hours for an entire advancement program. Her point is that the board and head need to budget for the actual time the work requires, plus a year of mentoring, so a promising hire has a fair chance to succeed and stay.Advancement is a prong of the financial strategy, and the head is a key partner in it. The largest gifts rarely move forward without the head’s involvement, because transformational donors want to hear the strategy from the person leading the school. Jill coaches some heads specifically on their fundraising role, and she encourages schools to treat development as a fully planned part of the financial model rather than an add-on.

  2. Oct 26

    The Living Endowment: How One School Turned Auxiliary Programs Into a Quarter of Its Budget (Rebroadcast)

    A quick note before you press play. This is one of my most popular episodes, and I share it with schools in my consulting work all the time. I'm bringing it back under a new title, The Living Endowment: How One School Turned Auxiliary Programs Into a Quarter of Its Budget, because the central idea feels more relevant now than when we first recorded it. If you've heard it before, I think you'll hear it differently with that frame in mind. If it's new to you, I hope it sparks a conversation with your team about the revenue you can build and control yourself. My guest is David Sullivan, Senior Advisor at SPARC, the Summer Programs and Auxiliary Revenue Collaborative, which supports independent schools in building strong auxiliary and summer programs. Before joining SPARC, David spent 16 years leading Breakwater School in Portland, Maine, and this episode is the story of what that school community built together. What if the most valuable gift a donor could give your school wasn't a million dollars for the endowment, but the advice to stop asking for it? That question sits at the center of Breakwater's turnaround. When David arrived in 2007 as the sixth head in seven years, the school was carrying a $350,000 deficit on a $2.5 million budget, a strategic plan built on enrollment growth that never came, and then a recession. One of the school's leading donors offered a different way forward: a million-dollar gift would yield perhaps $40,000 to $50,000 a year in draw, but investing in a business that earned net revenue every year would create a living endowment. Every $40,000 to $50,000 in net auxiliary income works like having a million dollars in the bank. Over the next 16 years, the Breakwater community grew auxiliary revenue from under 3 percent of the budget to about 25 percent, the budget grew to $4.5 million, and the school moved out of deficit, funded a facilities reserve, and began building its true endowment. This conversation is worth revisiting because the money was only part of the return. David describes how the school bused public school students into after-school programs; how faculty embraced the idea that every classroom belonged to the school and could be used year-round; how the auxiliary director joined the leadership team; and how part-time specialists gained full-time roles combining day and afternoon teaching. Breakwater eventually reincorporated as a learning center, which opened the door to foundation funding, broadened the board, and gave faculty a sense of public purpose. Enrollment grew from about 125 to 175 before COVID, partly because families first met the school through its programs. For heads and boards looking for a revenue lever they can control, Breakwater's experience offers both the mindset and a practical roadmap to get started. Five Top Takeaways 1. A living endowment earns every year, and it can be measured against the real one. The donor's math anchors the episode. At a typical draw rate, a million-dollar endowment produces roughly $40,000 to $50,000 a year, so a program netting that amount does the same work for the budget without requiring a million-dollar campaign. Framing auxiliary revenue this way gives boards a familiar yardstick for an unfamiliar line item. 2. Auxiliary positions should be evaluated as investments rather than costs. Breakwater learned to ask a different question when someone proposed a new auxiliary hire. For the day program, the reflex is to ask how much a position will hurt the budget. For auxiliary, the better question is how much it will help. The school lost money in year one, broke even in year two, and then grew at least 20 percent a year for over a decade, which is the pattern of a business that needed startup capital to reach scale. 3. The returns extend well beyond revenue. Auxiliary programs helped Breakwater retain and attract faculty, convert public school families into day students, build goodwill with the city, and recruit board members who otherwise would never have connected with the school. David's image is the Swiss Army knife: one investment that serves admissions, advancement, staffing, and community relationships at the same time. 4. Donors respond to being asked for an investment rather than a subsidy. When a grandparent offered a gift for the maker space, the school asked for three times the amount and explained that it would serve kids who lacked access to such a space and generate revenue for years. For business-minded donors, the language of investing in a venture that reduces the school's dependence on future gifts proved more compelling than another annual ask, and some came back for the next venture. 5. A growing auxiliary program reveals how well the whole school is running. David calls auxiliary the canary in the coal mine. Because it touches facilities, food service, athletics, academics, and communication, a growing program will bump against every weak system in the school. Rather than treating that friction as a problem, he encourages leaders to read it as diagnostic information about where the operation needs attention.

  3. Oct 19

    How the International School of Portland Became a Top Place to Work

    What does it take for a school to be named a Top Workplace in its city when it never set out to win the award? Bodo Heiliger, Head of School at the International School of Portland, leads a pre-K through fifth grade language immersion IB school of just under 400 students learning in Japanese, Mandarin, and Spanish. Roughly 80 percent of his employees grew up outside the United States, and Bodo describes the Top Workplace recognition as the cherry on top of years of deliberate work: climate checks, small touch points, constant requests for feedback, and a leadership team that went looking for the excellence already happening in classrooms so it could name it and celebrate it. Adopting the IB gave three language tracks a shared definition of good teaching, and cross-track collaborative planning turned three separate schools into one coherent experience for kids. The conversation reaches well beyond the staff room. Bodo shares how ISP chose to lean into its downtown Portland location, including partnering with City Hall and neighbors when a transitional houseless village opened across the street, a relationship that now shapes how students understand their role in the community. In the extended conversation for Moonshot Lab members, we get into the operating side of culture: bringing after-school programming in-house, giving extended day staff full-time status so they become part of the faculty community rather than an add-on, treating a summer camp of roughly 600 children as a meaningful enrollment opportunity, and building the endowed Spear Center for Teaching Excellence into both a professional learning engine and a bridge to public school educators. Bodo closes with how he knows culture is working, pairing retention data and an external benchmark with something harder to measure but just as real: whether you hear laughter when you walk the building. Top 5 TakeawaysBelonging Is Built on Intentional Systems: Earning recognition as a top workplace isn't about aiming for a title; it is the natural byproduct of continuous climate checks, feedback loops, and creating psychological safety for a diverse faculty.Cross-Track Collaboration Drives Coherence: Bringing teachers and students together across distinct language tracks around shared inquiry topics, such as marketing or revolutions, breaks down organizational silos and elevates teaching quality.Auxiliary Programs Are Strategic Drivers: In-housing after-school care and hiring language-specific, full-time staff turns extended-day programs into seamless cultural extensions, improving retention and generating meaningful revenue.Lean Into Your Local Context: Rather than isolating the campus, active engagement with local city leadership and neighborhood initiatives, such as partnering with a nearby transitional housing village, teaches authentic, local-first global citizenship.Endowed PD Centers Create Long-Term Value: Establishing an external-facing professional learning center elevates internal teacher leadership, attracts public school partners, and serves as a foundational bridge for future capital campaigns.

  4. Oct 12

    From 134 to Nearly 200 Students: The Power of Getting the Fundamentals Right

    What if meaningful enrollment growth comes from getting the fundamentals right, week after week, rather than from a sweeping overhaul? Pete Moore, Head of School at Oak Hill School in Eugene, Oregon, joins me to talk about how his team grew from 134 students to nearly 200 over three years. Pete describes it as compound decision-making: small, thoughtful choices made consistently until they start to add up. We talk about how that played out across parent communication, the look and feel of campus, and the standard operating procedures that now carry much of the school's daily work. What stood out to me is how much of this began with listening. Pete and his team listened closely to what families and staff were telling them, found where friction kept showing up, and built simple checklists and routines to address it. Over time, that steady attention to detail built trust across the community, and that trust became the foundation for financial stability, community pride, and a better experience for students. For heads, trustees, and senior administrators who are stretched thin and wary of quick fixes, this conversation offers a practical, encouraging model for lasting growth. Top 5 TakeawaysThe Power of Compound Decisions: Sustainable institutional growth relies on small, consistent, and thoughtful operational improvements made over time rather than a single major initiative.Trust Drives Retention: Small operational friction points, such as disorganized communication or chaotic event logistics, erode parent trust, making fundamentals the true foundation of enrollment.Standard Operating Procedures as Institutional Assets: Building comprehensive checklists and conducting post-event reviews ensure seamless execution, reduce administrative burnout, and preserve institutional memory.Enrollment Is a Lagging Indicator: Compounding efforts require patience; noticeable enrollment gains often follow two or three years of disciplined, behind-the-scenes operational refinement.Proactive Positive Communication: Structured outreach programs, such as intentional, frequent positive updates to families, strengthen community connection and turn parents into active advocates.

  5. Oct 5

    How to Know When Fractional Support Is Right for Your School

    What does it mean for a school to go fractional? After my conversation with Pete Moore of Oak Hill School, I heard from more listeners about fractional services than almost any other topic, and nearly all of them were asking some version of that question. So I invited back two people who do this work every day: Mattingly Messina, Founder of Throughline, who serves schools in advancement and fundraising, and David Hanson, Founder of Winthrop and Associates, who supports the business side of schools with services that include fractional CFO and COO work. Together, they offer a clear working definition, separating fractional from interim and outsourcing, and explain why this model is gaining momentum as schools look for specialized expertise that may not exist in their local market. From there, the conversation moves from definition to decision, anchored by a simple four-step framework David and Mattingly use to help schools decide whether and how to go fractional. Mattingly describes three types of schools that benefit from fractional support, from the well-resourced school managing a transition to the smaller school that treats a fractional leader as its long-term solution. David shows how an enterprise risk framework, built in the fall to inform the winter budget, helps schools plan for fractional help before a crisis instead of during one. They share what a strong engagement looks like in practice, including weekly reporting, a seat at leadership team meetings, and a scope built around the real rhythm of the work. The episode closes with David walking through that framework step by step. Schools start by assessing their needs, capacity, and gaps. They then clarify what stays in-house and what the fractional partner will own, evaluate both the financial case and the practical considerations of giving an outside partner access to systems and data, and finally plan what success should look like a year or 18 months out. David encourages schools to spend the most time on that last step, and both guests share a belief that the best fractional partners leave a school stronger than they found it. Want to put this framework to work at your school? David and Mattingly built two free resources to go with this conversation: the Fractional Pathway Matrix and the Fractional Readiness Discussion Guide. Bring them to your next leadership team or board conversation to map where fractional support fits and talk through whether your school is ready. Get both resources here. Top 5 TakeawaysFractional Leadership is an Intentional Strategy, Not Just an Interim Fix: True fractional engagements are planned, strategic decisions that bring specialized expertise into key roles, differing from emergency interim solutions designed solely to fill a vacant seat.Focus on Specialized Skill Sets Over Cost Savings: While fractional roles can save money, treating them purely as a cost-cutting measure often leads to mismatched skills; the main value lies in acquiring targeted, high-level expertise when needed.Enterprise Risk Management (ERM) Drives Talent Strategy: Aligning fractional needs with an Enterprise Risk Matrix allows leadership teams to identify operational gaps early and budget for specialized help well before a crisis occurs.AI and Evolving Tools Will Reshape Staffing Models: Non-student-facing departments, such as advancement and finance, are expected to shrink in direct full-time count over the next decade as automation takes hold, and fractional expertise fills remaining gaps.Fractional Leaders Must Be Fully Embedded: To succeed, fractional experts need deep engagement, participating in weekly leadership team meetings and building trust across campus rather than operating as distant outside consultants.

  6. Sep 28

    Designing the Organizational Health Dashboard for Independent Schools

    How can independent school leaders transition from fragmented departmental data to a unified system that accurately measures organizational health? In this episode, Cara Gallagher, founder of Cara Gallagher Consulting, returns to discuss how integrating behavioral science and organizational psychology allows leadership teams to build dynamic organizational health dashboards. By consolidating siloed indicators- spanning enrollment metrics, employee retention, financial variance, and workplace sentiment- into a single strategic perspective, schools can shift from reactive management to long-term sustainability. The discussion emphasizes framing internal metrics as shared evidence rather than departmental evaluation. Gallagher introduces a three-part behavioral framework: Align, Execute, and Renew, that helps executive teams and boards build data literacy, break down administrative silos, and ground strategic planning in clear organizational realities. Ultimately, this systems-oriented approach helps school leaders build strategic trust, support workplace satisfaction, and safeguard institutional health. 5 Top TakeawaysIntegrate Siloed Data to Reveal Organizational Systems: Viewing administrative, financial, and climate indicators within a single health framework transforms isolated departmental metrics into a comprehensive picture of institutional health.Frame Metrics as Evidence for Collaborative Inquiry: Presenting organizational data as shared evidence rather than individual evaluations fosters psychological safety and encourages constructive dialogue across administrative teams and boards.Anchor Long-Range Strategy in Present Organizational Reality: Conducting a thorough audit of existing institutional data provides a clear baseline, ensuring multi-year strategic plans address immediate priorities and real conditions.Organize Strategic Execution Around Behavioral Frameworks: Structuring leadership reflection around three key phases—Align, Execute, and Renew—translates broad institutional goals into measurable daily actions and long-term adaptability.Develop Organizational Data Literacy to Strengthen Governance: Cultivating shared data literacy among trustees and senior leaders grounds board conversations in strategic inquiries rather than operational assumptions.

  7. Sep 21

    Designing Systems for Head of School Longevity and Board Alignment

    In this episode, Ann Snyder, Vice President for Strategic Initiatives at NAIS, joins the podcast to explore leadership longevity, board alignment, and organizational design across independent schools. With average headship tenures shrinking and roughly 20% of new leaders transitioning within their first three years, establishing proactive alignment mechanisms early in a head’s tenure has become a cornerstone of institutional stability. The conversation centers on shifting leadership transitions from transactional search cycles toward structured, long-term onboarding systems. Snyder introduces strategic frameworks designed to build cohesion between boards and executive teams, including appointment charters, realistic job previews, and distributed governance models that integrate senior leaders directly into board conversations. By framing leadership transitions around shared expectations, transparent data-sharing, and continuous dialogue, independent school leaders can cultivate strategic trust and position their communities for long-term impact. 5 Top TakeawaysEstablish Early Strategic Alignment Through Appointment Charters: Formulating an explicit appointment charter during onboarding establishes clear, shared expectations and measurable focus areas between the board and the new head, laying a stable foundation for multi-year strategic progress.Implement Realistic Job Previews to Bridge Expectation Gaps: Move beyond traditional search prospectuses to provide comprehensive, operational snapshots so prospective leaders can assess institutional dynamics accurately and align their expertise with the school's actual needs.Integrate Senior Administrative Teams into Governance Cadences: Broaden board engagement to include key administrative leaders to foster distributed leadership, deepen trustees' contextual understanding, and strengthen succession capacity across the administrative structure.Shift Leadership Evaluation from Reactive Reviews to Continuous Dialogue: Regular alignment meetings between the head of school and the board chair ensure consistent feedback loops, reduce operational surprises, and strengthen strategic trust.Cultivate Multi-Perspective Signal Tracking: Assessing institutional indicators, such as enrollment shifts and financial trends, through diverse internal perspectives helps boards and executive teams distinguish underlying systemic dynamics from immediate market noise.

  8. Sep 14

    100+ Episodes: What I Have Learned Building MoonshotOS

    To celebrate more than a hundred episodes, I handed over the microphone. Pete Moore, head of school at Oak Hill School, reached out with an idea: flip the format and let him interview me. We covered my career supporting independent schools, the companies I started at the dawn of the internet, why I named the company MoonshotOS, and the calls I made to heads of school in the fall of 2023 that told me the pressure on the business model wasn't something I was imagining. Pete also asked me to reflect on more than a hundred episodes of the podcast. I have recorded more than four hundred episodes across four different shows, and a good part of how I program this one is selfish. I don't have the answer, so I find someone who has done that well and ask them about it. That is why I understand the intricacies of the school business model far better than I did when I started this show. The rest of the conversation gets into where a school should start when everything feels overwhelming. My thanks to Pete for his questions. Reflection is a practice I keep, and I am always grateful for another occasion to do it, particularly when someone else is choosing the questions. 5 Top TakeawaysThe pressure on the business model is real, and discovery calls confirmed it. Calling heads of school in the fall of 2023 turned a hunch into evidence. Hiring, enrollment, birth rates, and discounting kept surfacing in the same conversations.The independent school business model is challenged, not broken. We talked about that in the conversation, because the word matters. Broken suggests the thing needs replacing and invites panic at the board table. Challenged points to specific pressures a leadership team can identify and work on.What the market says it wants shifts, so validate before you build. Ask the same questions of everyone you talk to, because patterns only show up when the questions are consistent.Getting to root cause beats reacting to the symptom. Enrollment declines build quietly over years. Pulling one lever against the number you can see usually buys very little.Consistency is what makes a podcast work, not production value. Four hundred episodes across four shows, and the ones that lasted were the ones where the topic still held my interest three years in.

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Curious about the latest trends and breakthroughs in independent schools reimagining the business model? The Independent School Moonshot Podcast, packed with real-world examples, is just what you need!

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