February 3, 2026

Bridging Campus to Career with Dana Stephenson

How can educational institutions work together with employers to best prepare students for the workforce? Dana Stephenson recommends that they design scaffolded work experiences for students.

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About the episode

In this episode, Dana Stephenson, the co-founder and CEO of Riipen, offers a comprehensive framework for how education can shift to set students up for stronger careers. He makes the case that the classroom and on-the-job learning should be united, not separated, and offers several ways to implement this. He describes how part-time or remote work can be incorporated into a student’s schedule, and offers a ‘scaffolding’ model to help scale students up from short-term, low-stakes work projects to longer-term, high-stakes initiatives.

Dana makes the case for a tighter feedback loop between educators and employers. He argues that employers should be letting educators know what prepares students for the workforce, and what doesn’t. He also goes into some of the character-building benefits of working a job that students stand to benefit from.

Finally, Dana advises students to pick a major that genuinely motivates them and to prioritize programs with experiential learning. He closes with some thoughts on how AI will change the way startups do business.

Mentioned in the episode

Riipen – Dana’s company. A project-based learning platform for educators, learners, and employers.
Council of Independent Colleges – A partner of Riipen.
U.S. Chamber of Commerce’s Employer Provided Innovation Challenges (EPIC) initiative – A project-based learning initiative from the U.S. Chamber of Commerce that also partners with Riipen.

Host

Will Geiger

Will Geiger is the co-founder of Scholarships360 and has a decade of experience in college admissions and financial aid. He is a former Senior Assistant Director of Admissions at Kenyon College where he personally reviewed 10,000 admissions applications and essays. Will also managed the Kenyon College merit scholarship program and served on the financial aid appeals committee. He has also worked as an Associate Director of College Counseling at a high school in New Haven, Connecticut.Will earned his master’s in education from the University of Pennsylvania and received his undergraduate degree in history from Wake Forest University.

Guest

Dana Stephenson

Dana Stephenson is the Co-Founder and CEO of Riipen, a future-of-work platform dedicated to scaling experiential learning opportunities for learners of all backgrounds. Dana’s entrepreneurial journey began with a mission to end underemployment by ensuring every learner has access to authentic, career-relevant experiences that support a smoother transition into the workforce.

Under his leadership, Riipen has partnered with hundreds of academic institutions, non-profit organizations, and employers to make project-based learning more accessible and impactful for students everywhere. Dana works closely with universities, industry associations, and government agencies to expand experiential learning programs internationally, advancing both workforce readiness and educational innovation at scale.