Sasha Seymore

Co-Founder & COO
Learn to Win

Sasha Seymore is a co-founder and the COO of Learn to Win, an education technology company based in Redwood City, California, that improves training and onboarding for commercial enterprises, the Department of Defense, and athletic teams and programs. Sasha is also a reserve intelligence officer for the US Navy serving with the Defense Innovation Unit (DIU), helping the U.S. military make faster use of emerging commercial technologies.


Prior to Learn to Win, Sasha worked as a consultant for McKinsey & Company and played professional basketball in Europe. Sasha received an MBA from Stanford as a Knight-Hennessey scholar, an MA from Queen's University Belfast as a George Mitchell Scholar, and a BA from the University of North Carolina, where he was a Morehead-Cain Scholar, Senior Class President, and Scholar-Athlete of the Year on the men's basketball team. Sasha serves on the National Leadership Council for the Positive Coaching Alliance and was named to the 2022 Forbes 30 under 30 list in Education.