This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

Can a school truly shape its own word of mouth?

That's the challenge Head of School Torsie Judkins and strategist Barbara Egan (StoryScape) tackled at Wingra School in Madison, Wisconsin.

When enrollment lagged and perceptions didn't match campus reality, they partnered to uncover the real story the community needed to hear.

Through market research, thoughtful messaging, and disciplined storytelling, they distilled Wingra's essence into three clear, resonant ideas. These ideas empowered every stakeholder (teachers, trustees, and parents) to share a unified story.

This conversation reveals how message clarity transforms enrollment strategy, culture, and community confidence.

1. Treat enrollment like your primary revenue engine: Adopt business discipline in a nonprofit context. Put enrollment impact at the front of every programmatic decision.
2. Interdependence beats silos: Make CFO and enrollment leadership true partners. Strategic decisions should be cross-functional by design
3. Titles do not equal strategy: Shifting from admissions to enrollment management requires new responsibilities, decision rights, and data habits.
4. Pilot before you promise: Frame new initiatives as pre-launch pilots with clear thresholds for participation, dollars, and timeline. If thresholds are not met, sunset with transparency.
5. Clean data, longer horizon: Aim for five to seven years of usable enrollment data. Start where you are, improve data hygiene, and plan across multiple years, not just this cycle.

1. Convene the core trio: Schedule a working session with head, CFO, and enrollment lead to align on goals, roles, and nonnegotiables.
2. Run a program audit: Build a simple four-column sheet: program, revenue influence, expense, mission impact 1–10. Use it to surface what to keep, fix, or retire.
3. Design pilot criteria now: For any proposed program, set thresholds for enrollment lift, participation, cost, philanthropy, and decision date. Communicate them upfront.
4. Build three budget scenarios: Create best case, base case, and downside linked to enrollment targets and tuition outcomes. Share with the board and faculty.
5. Start the data clean-up: Commit to standard fields and definitions across systems. Backfill at least one prior year to begin a reliable five-year view.

Visit the episode page for complete details: https://www.moonshotos.com/how-to-build-an-enrollment-driven-strategic-plan

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

Visit the episode page for complete details: https://www.moonshotos.com/what-if-you-could-reclaim-time

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

What if AI could give independent school teams back hours each week without adding a single staff member?

This episode features Brendan Schneider, CEO of SchneiderB Media and long-time independent school marketer, exploring how AI is reshaping school marketing workflows.

Brendan shares real use cases from competitive research and persona development to website rewrites and simulated parent interviews that show how AI can help marketers move faster, think deeper, and spend more time on meaningful work.

The conversation examines how independent schools can use AI to address Baumol’s cost disease by creating real productivity gains where they have never been possible before.

• AI Adoption is Accelerating: Most schools have experimented with AI but have not yet integrated it into daily workflows. The next step is consistent use.
• AI Can Bridge the Staffing Gap: Marketing teams are under-resourced and rarely grow. AI can help offset that by automating repetitive or time-consuming tasks.
• Use AI for Deep Research: Move beyond writing copy. Use AI to analyze competitor websites, identify unique selling propositions, and surface blind spots.
• Prompting is a Skill: Apply the RACEQ framework (Role, Action, Context, Execute, Question) and keep refining prompts until the output is sharp.
• Train, Don’t Fear: Start small, experiment, and use tools like ChatGPT voice mode or custom GPTs to simulate parent conversations and strengthen strategy.

• Audit weekly marketing tasks and identify where AI could help.
• Create a one-page AI use policy outlining what is allowed, what is not, and how to stay ethical.
• Train staff in effective prompting using the RACEQ framework.
• Experiment with deep research prompts to compare messaging against competitors.
• Include a short “AI share” segment in team meetings to normalize learning.

Visit the episode page for all of the details!

➡️ https://www.moonshotos.com/why-every-head-of-school-needs-a-personal-brand

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

What does it look like when a head of school builds a personal brand that amplifies the school’s reputation? In this episode, Josh Clark, Head of School at Landmark School, shares how he has amplified the school’s visibility by intentionally developing his own professional presence as an extension of the school’s mission. From LinkedIn engagement to speaking and thought leadership, Josh shows how a strong head of school brand can serve as a multiplier for institutional awareness and impact.

He discusses how he partners with his communications team, how his experience with dyslexia informs his authentic communication style, and why heads of school must embrace an entrepreneurial mindset. Building your personal brand as a head of school, Josh explains, can elevate your school’s credibility and influence far beyond campus.

If you’re a head of school wondering how to position your brand, how to find your voice, share your school’s story, and balance external visibility with internal leadership, this episode is for you. Josh offers practical, authentic advice on how to start small, partner with your communications team, and show up consistently in ways that align with your school’s values and goals.

• Heads as storytellers: The head of school isn’t just a leader but the chief storyteller for the institution and its broader mission.
• External presence fuels internal impact: Speaking, posting, and networking externally can strengthen internal conversations and strategy.
• Partnership with communications staff is key: Having a trusted colleague translate ideas into posts ensures consistency and rhythm.
• Entrepreneurial mindset matters: Today’s heads must think like entrepreneurs, embracing uncertainty and finding inspiration outside the normal independent school circles.
• Brand awareness drives enrollment: Building thought leadership makes families view Landmark like a “teaching hospital,” a place where expertise is generated, not just applied.

• Audit your school’s communications strategy to ensure the head is visible as the chief storyteller.
• Schedule weekly or biweekly syncs with communications staff to align ideas and messaging.
• Encourage heads and leadership teams to engage on LinkedIn by sharing insights tied to the school’s expertise.
• Identify external conferences outside the education sector where your leaders can learn, connect, and share.
• Track how thought leadership activities correlate with inquiries, advancement opportunities, or partnerships.

Visit the episode page for full details.

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

Across independent schools, leaders are grappling with how to approach AI, with some banning it outright and others embracing it wholeheartedly. In the middle lies a growing interest in shared exploration and careful experimentation.

This episode examines Vail Mountain School’s collaborative approach, where students, faculty, and parents were all invited to participate in the AI conversation.

What began as a small student committee experimenting with new tools grew into a shared effort to shape policy, create guidelines, and teach peers about ethics, prompting, and responsible use.

In this episode, Kelly Enright, Director of Technology at Vail Mountain School, explains how giving students a leading voice has transformed the school’s approach.

From helping faculty draft department-level guidelines to running lessons for ninth graders, students helped create clarity while teachers gained confidence to experiment. For independent school leaders, it’s a practical example of how collective ownership can turn an overwhelming challenge into a community strength.

• Collaboration is the foundation: Students, faculty, and parents all contributed to shaping AI policy and practice.
• Student leadership drives impact: A student committee grew into a force influencing faculty and teaching peers.
• Policies must be iterative: Guidelines were refined department by department with feedback from students and teachers.
• Faculty buy-in matters: Teachers were given space to express their concerns and then encouraged to experiment safely.
• AI is a tool for growth: The emphasis remains on critical thinking, ethics, and student voice. AI enhances but doesn’t replace learning.

• Form a cross-community AI working group including students.
• Pilot one practical classroom use before scaling it up.
• Develop a tiered framework for AI use across assignments.
• Gather alum insights to prepare students for college and careers.
• Share success stories across the faculty to build momentum.

Visit the episode page for full details: https://www.moonshotos.com/a-strategic-plan-without-funding-is-just-poetry

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

What's the difference between a strategic plan that inspires and one that actually changes a school? In this episode, Mattingly Messina, advancement strategist and founder of Throughline, returns to the podcast and makes the case that the answer is money.

A plan without funding pathways, he says, is just poetry; beautiful language without impact.

We explore how to integrate financial planning early in the strategic process, the role of advancement leaders in shaping strategy, and why schools must get comfortable with sunsetting programs, not just adding more.

Messina makes the case for linking every strategic ambition to a realistic funding plan, providing independent school leaders with a practical framework for turning their vision into reality.

• Strategy without funding is fiction: Schools often create inspiring documents, but unless revenue sources are mapped, the plan remains aspirational.
• Day One vs. Day Two thinking: Begin with uninhibited ideation, but quickly move to financial feasibility to test which ideas can truly advance.
• Involve advancement early: Advancement leaders know donors, timelines, and feasibility; waiting until the end leaves them taking impossible “orders.”
• Addition must equal subtraction: True strategy involves tough choices, including sunsetting programs that drain resources without mission impact.
• Accountability matters: Leaders and boards should regularly audit plans against cost, funding source, and realistic timelines to avoid over-promising.

• Audit your current plan: For each initiative, ask, 'What does it cost?' Where will funds come from? What's the timeline?
• Engage your advancement team now: Don't wait until after priorities are set; bring them into the design process from the start.
• Create a program viability grid: Score programs based on revenue, cost, and mission impact to identify which ones to grow, maintain, or sunset.
• Build cross-functional task forces: Include CFOs, advancement, faculty, and board finance chairs in planning conversations.
• Document incremental wins: Track financial and strategic progress to hold leadership accountable and sustain board confidence.

Visit the episode page for full details: https://www.moonshotos.com/everyone-in-your-school-should-be-a-strategist

This episode of the Independent School Moonshot Podcast was originally released in August 2024 and is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

What if strategic planning in independent schools wasn’t a one-off exercise but a living, breathing practice woven into daily culture? In this episode, Alanna McKee, founder and CEO of Scarlet Oak Consulting, challenges schools to move beyond glossy one-pagers and accreditation checklists.

She makes the case for strategy as a continuous leadership mindset, anchored at the board level, carried through senior leadership, and embedded across faculty and staff.

Together, we explore how schools can balance bold ambition with realistic execution, operationalize strategy so it doesn’t collect dust, and create a culture of innovation where testing small ideas builds the muscle for bigger shifts.

Alanna also shares candid thoughts on revenue diversification, board governance, and how overwhelmed heads can get started without overcomplicating the process.

• Strategy is not a document; it’s a culture: Effective schools embed strategic thinking into boardrooms, leadership meetings, and faculty practices.
• Boards set the tone: Strong orientation, generative thinking, and tools like “Elmo, Enough, Let’s Move On” help keep them at the right altitude.
• Operational plans are non-negotiable: Without them, even the boldest strategic vision struggles to gain traction.
• Ambition must be matched with achievability: Schools must prioritize, make trade-offs, and build the endurance to test and scale ideas.
• Innovation grows from small experiments. Celebrating both wins and failures creates a safe environment and builds the innovation muscle across the organization.

• Audit your school’s current approach. Do you have a true operating plan tied to your strategic vision?
• Train your board and leadership team in generative thinking and strategic decision-making.
• Introduce small, low-risk experiments that test new ideas and build confidence in innovation.
• Tie KPIs directly to your strategic goals and make them a standing agenda item at board and admin meetings.
• Begin revenue diversification discussions with an openness to non-traditional streams that don’t dilute mission impact.

Visit the episode page for full details: https://www.moonshotos.com/what-moves-independent-school-families-to-enroll

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit https://blackbaud.com to learn more.

What if your school could attract families not by being everything to everyone, but by understanding what truly moves them to enroll?

In this conversation with Adam Olenn, CEO of Rustle & Spark and former Director of Communications at Moses Brown School, we explore "The Emotion Switch," examining how applied empathy, smart brand positioning, and authentic storytelling drive enrollment in independent schools.

Adam shares actionable insights on how emotion plays a central role in family decision-making, how to uncover what your school is genuinely great at, and why a mosaic of personal stories can shape a powerful, unified brand identity.

This episode is essential for school leaders rethinking how they communicate their value to the families they aim to serve.

What You'll Learn from Adam Olenn:

Emotions Drive Enrollment Decisions: Families often decide based on how a school makes them feel, not just what it offers. Emotion, not logic, is the final switch in decision-making.

Brand is What You're Known For: Your brand lives in the shorthand others use to describe you. The clearer and more differentiated this identity is, the more powerful your marketing becomes.

Different Beats Better: Instead of trying to be better than other schools, aim to be different. Positioning your school around a unique strength (e.g., entrepreneurship, community, diversity) creates a new category where you can be #1.

Empathy is a Strategic Tool: Applied empathy means deeply understanding what your audience feels and needs. Ask "why" multiple times to uncover the real motivations behind prospective families' questions.

Stories Convey Strategy: Real, personal stories bring your school's brand to life. A mosaic of authentic stories told through a common theme (like Beethoven's Fifth) helps families extract and extrapolate your school’s core values.

Recommended Next Steps

Map Your Brand Position: Identify what your school is truly known for in your local market. Compare with peers to find your unique place.

Gather Mosaic Stories: Ask faculty, students, parents, and alumni to share a specific time they experienced the school’s core value in action.

Interview Like a 4-Year-Old: Train your admissions and advancement team to ask "why" until they reach emotional bedrock. Use those insights to inform messaging.

Align Investments with Brand Strength: Use your brand identity to guide where to invest, choose the best language lab over the sixth-best STEM lab if it extends your school’s story.

Flip Faculty Storytelling: Ask teachers to "rat out" their colleagues doing great work. It opens up rich storytelling opportunities without self-promotion pressure.

Visit the episode page for full details: https://www.moonshotos.com/unlocking-your-leadership-superpowers-in-independent-schools

This episode of the Independent School Moonshot Podcast was originally released in August 2024 and is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit https://blackbaud.com to learn more.

What does it really take to grow into leadership in independent schools?

Denise Musselwhite, former CIO at Trinity Prep and founder of Tech and Thrive, examines the traits, habits, and strategies that enable aspiring leaders to move forward with clarity and confidence.

Drawing on her journey to senior leadership, she shares practical ways leaders can identify gaps, practice new skills, and avoid being "boxed in" by their current roles.

This conversation digs into self-awareness, the role of coaching and assessment, and why schools must rethink how they evaluate and nurture talent.

Denise challenges leaders to embrace self-advocacy, leverage uniqueness as a strength, and create opportunities inside and outside their schools. Independent school leaders at all levels will find both inspiration and practical tools to enhance their leadership journey.

What You'll Learn from Denise Musselwhite:

Self-awareness is foundational: Leaders must identify their value proposition and acknowledge experience gaps early on.

Data-informed coaching accelerates growth: Assessments like the CDR provide leaders with a clear mirror of their strengths, motivations, and derailers.

Don't wait for opportunities: Aspiring leaders should create them by volunteering, taking on projects, or engaging in external leadership roles.

Schools must evolve their evaluations: Teaching assessments often fail to measure leadership; schools need competency models that accurately reflect leadership qualities.

Uniqueness is a superpower: Leaders who embrace rather than hide their distinct background and strengths often unlock their most significant impact.

Recommended Next Steps

Conduct a self-inventory: Map your strengths, motivations, and areas for improvement, either using an assessment tool or engaging in structured reflection.

Practice outside your comfort zone: Take on roles that stretch interpersonal and vision-setting skills, especially if you come from non-academic tracks.

Reimagine meetings: Streamline agendas to include roadblocks, celebrations, and blue-sky thinking, making space for innovation.

Advocate for leadership competencies: If your school doesn't define them, suggest creating a competency model to clarify expectations.

Reframe self-promotion as advocacy: Share your story and strengths openly, recognizing the impact your example may have on others.

Visit the episode page for full details: https://www.moonshotos.com/the-changing-role-of-headship

This episode of the Independent School Moonshot Podcast was originally released in January 2024 and is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

What does it truly mean to be a head of school today?

In this episode, guest Mark Crotty, former Executive Director of NWAIS and now Consultant and Partner at Educators Collaborative, explores how the role of headship has evolved.

He unpacks the shifting expectations for heads, the growing complexity of the job, and what aspiring leaders should know as they consider stepping into this demanding but rewarding role.

From loneliness in leadership to the board–head dynamic, Crotty offers hard-won insights from more than 40 years in independent schools.

For school leaders and boards, this episode is both a wake-up call and a guidepost. Crotty emphasizes the importance of clarity, self-awareness, and team building, while also challenging schools to rethink how they prepare and select future heads.

The conversation frames headship not simply as management of an institution, but as a calling grounded in service, vision, and the ability to see possibilities for others.

• Headship is now more complex and externally focused: Today’s heads must juggle marketing, fundraising, facilities, and brand management in ways that weren’t as central 25 years ago.
• The loneliness of leadership is real: With no true peers inside their school, heads need intentional coaching, mentorship, and support systems.
• Boards are both vital and challenging partners: Misalignment around strategy vs. operations creates tension; boards must see hiring a head as their most important strategic decision.
• Aspiring heads must start with the “why”: Motivation matters. A desire for service, not just the title, sustains leaders through the demands of the role.
• Team building is ongoing, not a one-time event: Heads must continuously shape leadership teams and practice distributed leadership to thrive.

• Aspiring leaders should reflect on their motivation: Write down why you want to pursue headship and test it against the realities Crotty describes.
• Current heads should build intentional support systems: Invest in a coach or peer group to counteract leadership isolation.
• Boards should reframe head searches: Evaluate not just resumes but the person’s long-term potential and how the board itself will support them.
• Leadership teams should embrace constant evolution: Use regular check-ins to assess how the team needs to shift as the school advances its vision.
• Schools should integrate business acumen training: Provide aspiring leaders with exposure to finance, governance, and external relations early.