INDEPENDENT SCHOOL STRATEGIST
Peter Baron
Strategist for independent schools
I work with independent schools to develop strategic plans and operating systems that help them win in their markets.
WHAT DRIVES THIS WORK
Independent schools are operating in the most competitive market they have ever faced. The schools that win are the ones that lead with strategy and execute with discipline.
I've spent 20+ years in the independent school community, working in ed tech, association leadership, and enrollment marketing. That breadth is what shapes my approach. I've seen these challenges from angles most strategists haven't, and that's what allows me to help schools build strategy that wins their markets.
ABOUT
Strategy shaped by 20+ years in the field.
My connection to independent schools isn't just professional. I attended Brewster Academy as a boarding student. I know firsthand how independent schools change lives, and that's always in my mind when I'm working with schools. This work is about creating more opportunities for students.
Over the past 20 years I've worked across virtually every corner of the independent school community. The Enrollment Management Association. Blackbaud. Whipple Hill. AdmissionsQuest. That work took me into thousands of schools and gave me a clear picture of where strategy breaks down and what it takes to build one that holds.
In conversations with more than 200 school heads, I kept hearing the same thing: the market is getting harder, the stakes are getting higher, and strategy isn't keeping pace. I built MoonshotOS to change that.
I hold a BA from Skidmore College and an MAT from Tufts University, and have served as a trustee for Wolfeboro Camp School, Historic Neighborhoods, and Emerald City Football Club.
MY WORK
Strategy is the work.
MoonshotOS is how I do it.
I founded MoonshotOS to give independent school leaders the business clarity, winning strategy, and operational systems their schools need to build a sustainable future. Every engagement starts with the same conviction: strategy has to be rooted in the business model, and it has to be built to execute.
The flagship is Strategy + School Operating System, a modern approach to strategic planning built specifically for independent schools. It combines a four-month strategic planning process with a full year of operating system support: annual planning, 90-day sprint cadence, weekly meeting structure, and monthly advisory. Co-delivered with David Hanson of Winthrop & Associates, this offering brings financial rigor, strategic clarity, and operational execution together in a single integrated engagement.
MoonshotOS also offers the School Operating System as a standalone engagement, the Business Model Retreat as a one-day diagnostic, and Moonshot Lab as an ongoing membership for leaders building business acumen at every career stage.
BACKGROUND
20+ years serving the community.
MoonshotOS
Founder - Strategy & leadership systems for independent schools
Enrollment Management Association
Chief Member Relations Officer - Community building, member growth, marketing, research, leadership programs
Blackbaud & WhippleHill
Senior Leader - Product evangelism, partner ecosystem, marketing & relationship development
AdmissionsQuest
Leader - Enrollment strategy & school partnerships
Education
Brewster Academy · Skidmore College (BA) · Tufts University (MAT)
Board Service
Wolfeboro Camp School · Historic Neighborhoods · Emerald City FC
PODCAST
Each week I sit down with heads of school, board leaders, and senior administrators for honest conversations about what it actually takes to lead a financially sustainable independent school. A new episode every Monday. Free, wherever you listen.
Let's stay in touch.
If you're a school leader thinking about strategy, sustainability, or what it takes to build a school that's still thriving in 20 years, I'd like to know you.
Peter Baron
© 2026 Peter Baron