Head of Schools

KaiPod Learning • Boston, MA

2d • Remote

About The Position

KaiPod Learning operates a network of microschools across 21 states, aiming to make preferred schools accessible and affordable. The company partners with educators to start microschools through its accelerator program and builds a technology platform to support these schools. As Head of Schools, you will lead the function responsible for ensuring schools in the network have the necessary systems, support, and strategic guidance to be strong, sustainable, and high-quality. This role involves building the playbook for a new generation of schools, supporting company-operated sites and partner schools, and working at the intersection of school leadership, coaching, operations, and product strategy.

Requirements

• 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.
• Ability to travel and visit partner sites, as needed.

Responsibilities

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed