The Fintech Behind School Choice: How ClassWallet Moves $1.5B to Families and Schools with Jamie Rosenberg

Send us Fan MailJamie Rosenberg is the Founder and Executive Chairman of ClassWallet, a fintech platform modernizing how public education funds are distributed to schools and families. A longtime social impact entrepreneur, he previously founded AdoptAClassroom.org and has spent over two decades focused on getting dollars closer to students.💡 5 Things You’ll Learn in This EpisodeWhy education funding breakdowns are often about infrastructure, not intentHow ClassWallet replaced reimbursement with real-time, compliant digital walletsWhat it takes to run ESA and school choice programs at scaleHow empowering teachers and families unlocks creativity and efficiencyWhere AI and data can maximize the impact of every education dollar✨ Episode Highlights[00:02:31] Jamie’s journey from AdoptAClassroom to building ClassWallet [00:09:07] Why reimbursement systems create massive friction in education funding [00:13:55] How simple purchases (like pencil sharpeners) can unlock learning time [00:22:35] ClassWallet’s role in scaling ESAs and the modern school choice movement [00:33:01] What edtech founders need to know about accessing ESA-funded markets [00:41:58] Why supplemental funding is critical for students with special needs [00:47:12] How AI will shape compliance, recommendations, and impact measurement😎 Stay updated with Edtech Insiders! Follow us on our podcast, newsletter & LinkedIn here.🎉 Presenting Sponsor/s:Innovation in preK to gray learning is powered by exceptional people. For over 15 years, EdTech companies of all sizes and stages have trusted HireEducation to find the talent that drives impact. When specific skills and experiences are mission-critical, HireEducation is a partner that delivers. Offering permanent, fractional, and executive recruitment, HireEducation knows the go-to-market talent you need. Learn more at HireEdu.com. This season of Edtech Insiders is brought to you by Cooley LLP. Cooley is the go-to law firm for education and edtech innovators, offering industry-informed counsel across the 'pre-K to gray' spectrum. With a multidisciplinary approach and a powerful edtech ecosystem, Cooley helps shape the future of education. Tuck Advisors was founded by entrepreneurs who built and sold their own companies, frustrated by other m and a firms, they created the one they wished they could have hired but couldn't find. One who understands what matters to founders and whose North Star KPI is the percentage of deals closed. If you're thinking of selling your ed tech company or buying one contact Tuck advisors now. Every year, K-12 districts and higher ed institutions spend over half a trillion dollars—but most sales teams miss the signals. Starbridge tracks early signs like board minutes, budget drafts, and strategic plans, then helps you turn them into personalized outreach—fast. Win the deal before it hits the RFP stage. That’s how top edtech teams stay ahead.