Ryan is a Managing Director at Achieve Partners and was formerly an MD at University Ventures. Ryan’s commentary on where the puck is going in education and workforce regularly appears in the biweekly Gap Letter, Forbes, and Inside Higher Education. He is the author of the book Apprentice Nation: How the "Earn and Learn" Alternative to Higher Education Will Create a Stronger and Fairer America (2023). He is also author of A New U: Faster + Cheaper Alternatives to College (2018), which describes the critical importance of last-mile training and the emergence of bootcamps, income share programs, staffing and apprenticeship models as preferred pathways to good first digital jobs and was named in the Wall Street Journal as one the Books of the Year for 2018. Ryan’s first book was College Disrupted: The Great Unbundling of Higher Education (2015), which profiles the coming shift toward competency-based education and hiring. Ryan is a co-founder of Apprenticeships for America, a national nonprofit dedicated to scaling apprenticeships across the U.S. economy, a member of the Los Angeles County Workforce Development Board, and a senior fellow at the Progressive Policy Institute.

Previously, Ryan led the Education & Training sector at Warburg Pincus. His prior experience in higher education was at Columbia University. Ryan also founded and built Wellspring, a national network of boarding schools and summer camps for overweight and obese children, adolescents, and young adults. He began his career at McKinsey & Co.Ryan received bachelor's degrees summa cum laude and Phi Beta Kappa from Yale University, and his law degree from the Yale Law School.‍