Send us a text

Jamie 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 Episode

Why education funding breakdowns are often about infrastructure, not intent
How ClassWallet replaced reimbursement with real-time, compliant digital wallets
What it takes to run ESA and school choice programs at scale
How empowering teachers and families unlocks creativity and efficiency
Where 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:

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.

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.

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.

As a tech-first company, Tuck Advisors has developed a suite of proprietary tools to serve its clients better. Tuck was the first firm in the world to launch a custom GPT around M&A. If you haven’t already, try our proprietary M&A Analyzer, which assesses fit between your company and a specific buyer. To explore this free tool and the rest of our technology, visit tuckadvisors.com.

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

Edtech Insiders

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