Kelly Cassaro

Kelly Cassaro is a global leader in education, workforce development, and organizational transformation, focused on using AI and digital innovation to solve unemployment at scale and unlock human potential across systems. She is the Chief of Learning at Generation, a global education-to-employment nonprofit that prepares and places learners of all ages into careers previously beyond their reach. Kelly leads the design and scaling of online-first, role-specific training programs that have served more than 150,000 learners worldwide. Her work sits at the intersection of learning, technology, and organizational strategy, ensuring that Generation’s programs remain relevant in a rapidly changing labor market. Kelly is a driving force behind Generation’s enterprise AI strategy. She co-leads...