Head of Schools

KaiPod Learning • Boston, MA

3d • Remote

About The Position

KaiPod Learning operates a network of microschools across 21 states, aiming to make desirable schools accessible and affordable. The company partners with educators to help them start their own microschools through its KaiPod Catalyst program and builds the technology platform and services to support these schools. The Head of Schools role is critical to ensuring the success of school leaders and partners by providing systems, support, and strategic guidance for strong, sustainable, and high-quality schools. This role involves building a playbook for a new generation of schools, supporting company-operated sites and partner schools, and leading teams to help founders grow their schools. The position sits at the intersection of school leadership, coaching, operations, and product strategy.

Requirements

• 7+ years of experience in school leadership, customer success, or 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.
• Strong customer orientation with a focus on helping people succeed and building trust-based, supportive, and results-driven relationships.
• Demonstrated experience coaching school leaders, entrepreneurs, or operators in non-traditional settings.
• Comfort working across school operations, finance, enrollment and marketing, and academics.
• A bias toward action: resourceful, entrepreneurial, and excited to build in an environment with evolving priorities and emerging opportunities.
• Ability to work remotely with the capacity to travel and visit partner sites as needed.

Responsibilities

• Lead and scale KaiPod’s school success function across the network, ensuring the long-term health, satisfaction, and performance of schools.
• Define exceptional school success within the KaiPod Network and develop strategies to support founders in academics, operations, enrollment, and finance.
• Develop systems to coach school leaders in launching thriving, sustainable microschools with outstanding student and family experiences.
• Identify network-wide patterns and translate them into actionable improvements through playbooks, new services, and enhancements to the Newton operating system.
• Collaborate with cross-functional teams to ensure founder insights influence product development and school support at scale.
• Oversee the commercial health of company-operated sites and the partner network, including retention, renewal, expansion, and long-term school success.
• Hire, lead, and develop a team of account managers, setting clear outcomes, high standards, and fostering a culture of excellence.
• Act as a key company leader in defining the infrastructure for the next generation of schools.

What This Job Offers

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