Since 1990, Jay has partnered with like-minded parents and educators to provide quality educational opportunities for students in New Orleans open-admission public schools. He taught in the city for several years before co-founding New Orleans Charter Middle School. He was also a founder of James Lewis Extension School, New Orleans Outreach, New Orleans Summerbridge, and Leading Educators. As director of education for London-based ARK schools from 2005 to 2008, Jay helped develop a British network of academies, charter- like schools in complex urban environments. He also was instrumental in establishing two training programs there – Future Leaders for aspiring principals of open-admission schools, and Teaching Leaders for mid-level school leadership.