James Cryan

James believes every young person deserves a clear, high-quality path to economic opportunity. Not just college. Not just a job. A purpose-driven path that leads to a flourishing life. He is the Founder and CEO of Willow Education, PBC, a career exploration and postsecondary planning platform built for school systems working to strengthen purpose development, career readiness, and postsecondary outcomes. Willow’s vision is a world where all learners find quality next steps that enrich their lives through education, durable skills, and an economic return on their investment. The company’s mission is to help 10 million students choose quality education next steps by 2033. James also serves as a Senior Advisor to Harvard’s Next Level Lab at the Harvard Graduate School of Education, helping infuse the science of learning into K12 and workforce education. He writes the Purposeful Paths newsletter on Substack, challenging the “college for all” paradigm and advocating for a broader, more honest vision of preparing young people for the future. Previously, James founded Rocky Mountain Preparatory Schools (RMP), a network of 12 high-performing, nonprofit public charter schools serving approximately 5,000 students across the Denver Metro Area. The network earned recognition from the State of Colorado, Denver Public Schools, and Colorado Succeeds for exceptional student growth and achievement, and The Denver Post named RMP one of Denver’s Top 100 Workplaces three times during his tenure. James has been named one of Colorado’s “Public Education Game-Changers” by A+ Colorado and “Leader of the Year” in 2021 by the Colorado League of Charter Schools. He currently serves as co-chair of the Middlebury Area Land Trust board and has served as an entrepreneurship mentor and lecturer at MIT, Middlebury, and Champlain College. James holds an MBA from the University of Denver, was a member of Teach for America, and graduated magna cum laude from Colby College. He lives in Vermont with his wife Liz, a pediatrician, and their three children. When they’re not working, you’ll find them hiking, biking, skiing, or getting dirt under their fingernails in the garden, chicken coop, or beehive.