Informed by his undergraduate and graduate work at Middlebury College and Columbia University’s Klingenstein Center, Josh Cobb built an extensive career in education, culminating in his role as Head of School at Graland Country Day School. He initially joined Graland as an English teacher before advancing to Head of Middle School for seven years. His leadership further expanded to Head of School in 2017. For nearly a decade, he has lead Graland, while focusing primarily on creating a dynamic culture of growth for both students and educators. In 2025, one of these efforts, the Sphere Compensation System, was recognized nationally with the NBOA Jeffrey Shields Innovation Award. Outside of Graland, he is proud to serve as the Association of Colorado Independent School’s Board President. Informed by his undergraduate and graduate work at Middlebury College and Columbia University’s Klingenstein Center, Josh Cobb built an extensive career in education, culminating in his role as Head of School at Graland Country Day School. He initially joined Graland as an English teacher before advancing to Head of Middle School for seven years. His leadership further expanded to Head of School in 2017. For nearly a decade, he has lead Graland, while focusing primarily on creating a dynamic culture of growth for both students and educators. In 2025, one of these efforts, the Sphere Compensation System, was recognized nationally with the NBOA Jeffrey Shields Innovation Award. Outside of Graland, he is proud to serve as the Association of Colorado Independent School’s Board President.