HEADS BUSINESS STRATEGY GROUP
The business challenges facing independent schools are real. Working through them alone doesn't have to be.
Tuition strategy. Non-tuition revenue. Board financial literacy. Risk. These are the decisions shaping whether your school has runway five years from now, and they rarely have a clean answer.
This group exists to break them down together. Five to eight heads of school. One focused business topic a month. Real schools, real numbers, peers doing this work at the same time you are.
Included with Moonshot Lab Membership
The Numbers
5-8
Heads per group. Small enough that everyone talks, every session.
1
Focused business topic each month. No scattered agenda.
100%
Confidential. What's said in the group stays in the group.
10
Months a cohort typically runs together, so context compounds.
WHY THIS EXISTS
Every head is facing some version of the same business questions.
Now there's a place to think it through with peers.
Pricing ceilings. Discount rates. Non-tuition revenue. Board members who want a surplus without calling it profit.
These aren't questions with a textbook answer. They depend on your market, your history, your board, your community, and they shift year to year. Most heads end up working through them solo, piecing it together meeting by meeting, budget cycle by budget cycle.
The Heads Business Strategy Group takes a different approach. Same five to eight heads, meeting monthly, breaking down one real business topic at a time, sometimes with an outside expert, sometimes with a head bringing a live problem from their own school. Everyone in the room is doing this work in real time, at their own school, right now.
Not a webinar
No audience, no slides to sit through. Five to eight heads working through one real problem.
Not a one time event
The same cohort meets monthly, so context builds instead of resetting every session.
Not theory
Frameworks get tested against real numbers from real schools in the room, including yours.
Not public
Confidential by design. What gets said about your school stays with the group.
WHAT ACTUALLY HAPPENS
One topic. One hour. Real business problems, not theory.
Every session opens the same way. A quick round where each head shares a personal or professional win. It sounds small. It's what makes the rest of the hour work, because heads show up as full people, not just as their title. From there, the group works through one business topic in depth.
01
Managing up to the board
Where power actually sits in the head-board relationship, succession planning, and what to share in a head's report without inviting the board into operations.
02
Building an anti-fragile business model
Why the strengths that feel safest are often the most exposed, and how a barbell approach to resource allocation protects a school when conditions shift.
03
Tuition strategy and pricing
How to find your school's real pricing ceiling, what discount rate math actually tells you, and whether your school is more price-inelastic than you think.
04
Non-tuition revenue
Auxiliary programs, summer camps, facility rentals, and how to build the investment case for a new revenue stream before asking a board to fund it.
05
AI in daily practice
What's actually saving time right now, from strategic planning to notetaking to market research, and where AI hasn't yet moved the bottom line.
06
Competitive positioning
What it means to define winning on your own terms, without abandoning the mission that makes your school what it is.
Every topic gets tested against real schools in the room. Heads leave with something to try Monday morning, not a framework to file away.
Who this is for
Built for heads who want to think through hard business problems with people doing the same work.
You're a current head of school facing real financial, enrollment, or strategic pressure, and want peers wrestling with it too.
You want a group that carries context from month to month, not a new room of strangers every time.
You're open to being challenged on your thinking, not just supported.
You'd rather break down a live problem with people who've run a school than sit through a generic training.
You're looking for practical frameworks and real numbers, not theory.
WHAT CHANGES OVER TIME
What a year in the group actually builds.
01
A go-to group for the hard decisions
Tuition strategy, board dynamics, a new revenue idea you're not sure is worth the investment.
02
Sharper instincts on your business model
Twelve months of breaking down real topics with real peers builds pattern recognition no single workshop can.
03
Language you bring back to your team
Anti-fragility, barbell resource allocation, non-tuition core revenue. Concepts stress-tested by the group.
04
A standing relationship, not a one-time event
The same five to eight heads, month after month. That continuity is what separates this from a conference.
The Impact
“
Peter's passion for independent schools and their leaders is palpable. The Moonshot Lab experiences I have engaged with thus far have been thoughtful and intentional and designed to empower me to make the best business leadership decisions I can for my school's future.
Brenda Leaks
Head of School, San Francisco Friends School
MEET THE FOUNDER
Peter Baron built this group after hundreds of conversations with heads facing the same business questions.
Peter spent two decades working alongside heads of school, admissions directors, and boards on enrollment and sustainability challenges before founding MoonshotOS in January 2024.
The Heads Business Strategy Group grew directly out of a listening tour with heads across the country, all working through versions of the same business pressure, with nowhere built for them to break it down together.
HOW TO JOIN
The Heads Business Strategy Group is included with Moonshot Lab Membership.
There's no separate fee or application. Whether you enroll through Individual Membership or your school enrolls through School Membership, the current head of school receives a seat in a Strategy Group cohort as part of the package, along with expert coaching sessions, the AI Lab & Library, and access to all nine MoonshotOS advisors.
Groups are kept small on purpose, so seats are limited and matched by cohort timing.
COMMON QUESTIONS
Frequently asked questions
What is the Heads Business Strategy Group?
A confidential peer group of five to eight current heads of school who meet monthly to break down one focused business topic together. Sometimes with an outside expert, sometimes working through a live problem from one head's own school.
Is this only for heads of school?
Yes. It's the one part of Moonshot Lab reserved specifically for current heads. Aspiring leaders get full access to everything else in the Individual Membership, but the Strategy Group itself is limited to sitting heads.
How is this different from the Expert Lab Coaching Sessions in Moonshot Lab?
The coaching sessions are open to the whole Lab community and built around specific skills. The Strategy Group is smaller, confidential, and built around an ongoing peer relationship. Same faces every month, working through what's actually happening at each other's schools.
What if I'm not ready to talk openly about what's going on at my school?
That's normal at first. Every session opens with something low stakes, a quick personal or professional win, before getting into the business topic. Most heads say the trust builds faster than they expected, usually within the first two or three sessions.
Can I join the group without enrolling my whole school in Moonshot Lab?
Yes. If you're a current head of school, you can join as an Individual Member on your own; your school doesn't need to enroll you to get a seat. School Membership includes it too, and adds coverage for the rest of your leadership team. If you want help deciding which path fits, book a free 30-minute call.
Do I need to prepare anything before a session?
No. Just show up ready to think. If you have something specific going on at your school, you're welcome to bring it, but there's no required prep.
Member Resources
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