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

Jan 12, 2026

Jamie Rosenberg, the Founder and Executive Chairman of ClassWallet, shares insights on transforming education funding. He discusses how bureaucratic hurdles hinder dollars from reaching students and how ClassWallet's digital wallet streamlines this process. Rosenberg highlights the importance of empowering teachers and families to enhance creativity in learning. The episode delves into the scaling of Education Savings Accounts and the crucial role of AI in improving compliance and funding outcomes. A must-listen for those invested in education innovation!

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ANECDOTE

Mentorship Sparked A Funding Platform

Jamie built AdoptAClassroom after mentoring a pre-K student and seeing teachers lack easy funding access.
That wallet tech later scaled into ClassWallet to distribute billions and reach over 15 million children.

INSIGHT

Compliance Creates Friction, Not Lack Of Funds

Bureaucratic compliance often blocks money from reaching classrooms rather than lack of donor intent.
Jamie built technology to satisfy compliance while removing friction so funds actually flow.

ADVICE

Move From Reimbursement To Digital Wallets

Replace reimbursement with pre-programmed digital wallets to eliminate paperwork and retroactive claims.
Pre-vet vendors and automate transaction-level checks to keep spending compliant and auditable in real time.

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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

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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.

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