How do you build an AI-powered assistant that teachers will actually use? In this episode of Just Now Possible, Teresa Torres talks with Thom van der Doef (Principal Product Designer), Mary Gurley (Director of Learning Design & Product Manager), and Ray Lyons (VP of Product & Engineering) from eSpark. Together, they’ve spent more than a decade building adaptive learning tools for K–5 classrooms—and recently launched an AI-powered Teacher Assistant that helps educators align eSpark’s supplemental lessons with district-mandated core curricula. We dig into the real story behind this feature: - How post-COVID shifts in education created new pressures for teachers and administrators - Why their first instinct—a chatbot interface—failed in testing, and what design finally worked - The technical challenges of building their first RAG system and learning to wrangle embeddings - How their background in education shaped a surprisingly rigorous eval process, long before “evals” became a buzzword - What they’ve learned from thousands of teachers using the product this school year It’s a detailed look at the messy, iterative process of building AI-powered products in the real world—straight from the team doing the work.