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Head of Schools
KaiPod Learning
Boston, MA, USA
Posted on May 28, 2026
ABOUT US
KaiPod Learning operates a network of microschools across 21 states.
We believe deeply that every parent deserves the right to send their children to a school they love. Unfortunately, most parents cannot access these schools – either because they don’t exist near them or they’re simply unaffordable.
We are working to change that reality in two ways. First, we partner with exceptional educators to help them start their own microschools. KaiPod Catalyst, our school startup accelerator, is the largest in the nation and can cut the time and cost to start a school by 90%.
Second, we are building the operating system to power this new generation of schools. We are the fastest growing network of our kind anywhere and our technology platform and our services help these schools grow, have greater impact, and change the face of American education.
Our long-term vision is bold: to connect 1 million students globally through the power of microschooling. The name KaiPod comes from the Greek word kairos, meaning “the right moment to act.” For millions of families, that moment is now.
We’re backed by Y Combinator, Reach Capital, and other top-tier investors who believe in the future of personalized, place-based education.
ABOUT THE ROLE
KaiPod's success depends on the success of the school leaders and partners we serve. As Head of Schools, you will lead one of the most important functions in the company: ensuring that every school in our network has the systems, support, and strategic guidance to become strong, sustainable, and high-quality.
This is a rare opportunity to build the playbook for how a new generation of schools succeeds. You will support our national portfolio of company-operated sites and partner schools, building the systems and leading the teams that help Founders grow stronger schools over time. You will sit at the intersection of school leadership, coaching, operations, and product strategy.
Specifically, you will:
- Lead and scale KaiPod’s school success function across our network, owning the long-term health, satisfaction, and performance of the schools we serve
- Define what exceptional school success looks like in the KaiPod Network and build the strategy for how we support founders across academics, operations, enrollment, and finance
- Develop systems to coach school leaders who are launching thriving, sustainable microschools that deliver outstanding experiences for students and families
- Identify patterns across the network and turn them into action, through stronger internal playbooks, new services, and improvements to Newton, our microschool operating system
- Partner closely with our cross-functional teams to ensure founder insights directly shape what we build and how we serve schools at scale
- Own the commercial health of the company-operated sites and partner network, including retention, renewal, expansion, and long-term school success
- Hire, lead, and develop a strong team of account managers, creating clarity around outcomes, raising the bar for execution, and building a culture of excellence
- Serve as a key leader in the company as KaiPod continues to define the infrastructure that powers the next generation of schools
ABOUT YOU
You are a builder at heart. You love stepping into ambiguity, bringing order to complex challenges, and creating systems that help people thrive. You are equally comfortable thinking strategically at a high level and rolling up your sleeves to solve problems in real time.
You are energized by working with school leaders. You know what it takes to build something meaningful from the ground up, and you bring empathy and high standards to the people you support. You know how to build trust quickly, coach with credibility, and push for excellence.
You are excited by the opportunity to help shape a fast-growing company at an important stage. That means you are adaptable, low-ego, hungry to learn, and open to feedback. You thrive in environments where the playbook is still being written and your voice shapes what comes next.
More specifically, we are looking for candidates with:
- 7+ years of experience in school leadership, customer success, or other roles supporting school operators, founders, or education entrepreneurs
- Experience building, managing, or scaling account management or partner success teams, including defining success metrics, building systems, and developing team members
- A strong customer orientation. You are energized by helping people succeed and know how to build trust-based relationships that are both supportive and results-driven
- Demonstrated experience coaching school leaders, entrepreneurs, or operators in nontraditional settings
- Comfort working across school operations, finance, enrollment and marketing, and academics. You do not need to be the deepest expert in every area, but you can engage credibly and strategically across all of them
- A bias toward action. You are resourceful, entrepreneurial, and excited to build in an environment where priorities evolve and opportunities emerge quickly
Our team, along with our school network, spans the country. We are looking for strong candidates to work remotely and with the ability to travel and visit partner sites, as needed.