Winston Roberts wears many hats: former classroom teacher, AI Innovation Lead at Foundation Academies, graduate student at the University of Pennsylvania, and founder of Tailored for Education—a consulting platform offering AI training and keynotes to educators across the country. He’s spoken at South by Southwest EDU, ASU+GSV, ISTE, and dozens of AI summits, bringing a teacher’s clarity and a technologist’s urgency to conversations about what’s changing in schools.
But Winston’s deepest influence comes from his family story. His parents grew up in Flint, Michigan, where a teacher named Miss Blight predicted the factory collapse years before it happened. Few listened. A community was left behind. That history shapes everything Winston does now. His daughter was born the day before ChatGPT’s public launch in November 2022—and watching both grow up together has crystallized his conviction that teachers must see the trends, understand the stakes, and act with purpose.
Known as the “teacher in a suit,” Winston brings a classroom sensibility to complex conversations: practical, grounded in what actually works with students, and unafraid to challenge systems that have stopped serving learning. His work centers on helping educators find their authentic voice in an AI-enabled world—and ensuring that the tools available to the elite become tools available to all.
