From “Edtech Insiders” | Alex Sarelin and Jamie Rosenberg, Founder & Executive Chairman, ClassWallet
| Published November 24, 2025
A Conversation with ClassWallet Founder Jamie Rosenberg on EdTech Insiders
How Modern Financial Infrastructure Is Powering the Future of Education Funding
In this episode of EdTech Insiders, ClassWallet Founder & Executive Chairman Jamie Rosenberg joins host Alex Sarlin to unpack one of the most persistent challenges in education: how public funds actually move – and why outdated financial systems prevent dollars from reaching the students who need them most.
Drawing on more than two decades of experience at the intersection of education, technology, and public finance, Jamie explains how modern financial infrastructure can reduce friction, protect compliance, and expand opportunity for educators and families alike.
What you’ll learn in this episode
- Why compliance-heavy reimbursement systems limit impact at scale
- How ClassWallet replaces friction with guardrails – without sacrificing accountability
- What’s driving the rapid expansion of ESAs and school choice programs
- How supplemental funding supports students with special needs and neurodivergent learners
- Why financial technology is the linchpin for equitable, student-centered funding
EdTech Insiders Podcast Transcript
Host: Alex Sarlin
Guest: Jamie Rosenberg, Founder & Executive Chairman, ClassWallet
Introduction
Alex Sarlin:
Welcome to EdTech Insiders, the leading podcast covering the education technology industry. From funding rounds and impact to AI developments across early childhood, K-12, higher ed, and workforce learning—you’ll find it all here.
Remember to subscribe, check out our newsletter and event calendar, and for deeper access, join EdTech Insiders Plus for premium content, early event access, and back-channel insights from Ben and me.
For today’s interview, we’re joined by Jamie Rosenberg, founder and executive chairman of ClassWallet, a financial technology platform modernizing how public funds are distributed. A longtime social impact entrepreneur, Jamie also founded AdoptAClassroom.org and has dedicated his career to expanding opportunity and reducing inequality.
Jamie, welcome to EdTech Insiders.
Origins of ClassWallet
Jamie Rosenberg:
It’s great to be here, Alex. A pleasure to meet you.
Alex Sarlin:
Likewise. We don’t often talk to fintech platforms that are also clearly edtech companies, so I’m really curious about how ClassWallet operates—especially at this moment in public funding. Let’s start at the beginning. Can you share your background, how AdoptAClassroom.org came about, and how that journey led to ClassWallet?
Jamie Rosenberg:
Absolutely. At the core of everything I’ve done is a simple mission: get the dollar as close to the student as possible. Money empowers the people who can make the greatest difference in a child’s life, and that’s where education and financial technology intersect.
That journey started in 1998. I was a corporate attorney mentoring a student at a Miami pre-K school serving children with physical and cognitive disabilities. That experience changed my life. I wanted to be closer to helping students—and the people who help students.
At the time, there was no easy way to donate directly to a classroom teacher. You could give to a PTA or a school foundation, but teachers themselves – who arguably have the greatest impact—were hard to support directly. So I started AdoptAClassroom.org to streamline classroom-level giving.
What I didn’t realize at the time was that I was building wallet infrastructure. A donor could give $500 to a teacher in Philadelphia, but no money ever physically changed hands. The teacher received a digital wallet, spent the funds on approved resources, and the donor had full transparency – down to the penny – on how the money was used.
AdoptAClassroom grew to distribute about $25 million to teachers in 30% of U.S. public schools, with a staff of never more than two people. That showed me the power of financial technology to drive impact.
Around 2010, I realized this problem was much bigger than philanthropy. Lots of people were trying to get money into school systems—and struggling. That insight led to the launch of ClassWallet in 2014, where we took that bespoke system and built an enterprise-grade platform for districts and states.
Today, ClassWallet has distributed about $6 billion to teachers and families across 33 states. Combined with AdoptAClassroom, we’ve positively impacted the lives of over 15 million children.
Why Financial Flows Are the Bottleneck
Alex Sarlin:
That’s incredible. When did it click for you that how money flows was one of the biggest bottlenecks in education?
Jamie Rosenberg:
It was crystal clear from day one. Early on, I approached the Florida Marlins Education Foundation, and they said, "We’ve been trying to donate $15,000 to the school district for three years, and they won’t take the money."
That told me everything. The friction wasn’t a lack of goodwill—it was compliance, process, and bureaucracy. Everyone was trying to do the right thing, but compliance often trumped outcomes.
So we built technology that satisfies compliance requirements while removing gridlock, allowing dollars to move efficiently and have the impact they were intended to have.
How ClassWallet Works
Alex Sarlin:
Let’s dig into that. How does ClassWallet actually reduce friction while maintaining compliance?
Jamie Rosenberg:
ClassWallet replaces the reimbursement model.
Before us, beneficiaries—teachers, schools, families—would spend their own money, submit paper receipts, wait for approvals, and hope to get reimbursed. At scale, that’s incredibly inefficient.
ClassWallet is a digital wallet. A beneficiary receives funds – say $10,000 – and every rule about how those funds can be used is pre-programmed. Eligible? Yes. Ineligible? Blocked automatically.
We integrate with about 400 education vendors, including Amazon, Staples, Scholastic, Lakeshore, Best Buy, and many more. We also support:
- Direct pay (ACH, like Zelle or Venmo)
- Reimbursements
- Debit cards (when allowed)
Every vendor is vetted against program rules before entering the system. At the transaction level, we validate eligibility before payment happens. And everything – reconciliation, reporting, auditing – is automated in real time.
The result: compliance without friction, and maximum agency for the person closest to the student.
Empowering Teachers: Small Purchases, Big Impact
Alex Sarlin:
Do you have examples that really illustrate the value of this approach?
Jamie Rosenberg:
Two come to mind.
One teacher spent a significant amount of funding on Post-it notes. At first, that sounded unimpressive. But she used them as movable letter tiles—essentially a low-cost Scrabble system—for phonics instruction. It was creative, effective, and tailored to her students.
Another common purchase: electric pencil sharpeners in kindergarten classrooms. That doesn’t sound transformative – until you realize teachers were losing 15 minutes a day managing pencil sharpening. Multiply that across a year, and it’s a huge instructional loss.
The lesson is simple: trust educators. When you remove bureaucratic barriers and provide guardrails instead of red tape, creativity and efficiency flourish.
School Choice & ESAs
Alex Sarlin:
Let’s talk about school choice and ESAs. This is a huge moment for public funding.
Jamie Rosenberg:
Leaders in the school choice movement approached us around 2016. Early programs relied on debit cards, which created massive compliance issues.
The problem they faced was the same one we had already solved inside school systems. So we adapted ClassWallet for families.
Today, ClassWallet powers eight ESA programs and manages about $1.5 billion annually for families—set to nearly double. Since 2017, families have purchased 1.8 million unique items through ClassWallet.
Every child is different. ESAs allow families to personalize learning—devices, tutoring, therapy, books—while still maintaining accountability. That balance is what we’re built for.
What This Means for EdTech Companies
Alex Sarlin:
For edtech founders listening—how do they become part of this ecosystem?
Jamie Rosenberg:
ClassWallet is a two-sided marketplace. For vendors with e-commerce capabilities, integration is straightforward—we already support all major platforms. Even bespoke systems can integrate via a lightweight API in under six hours.
Our vendor team also helps companies navigate state-by-state compliance requirements. We’ve processed billions of dollars across dozens of programs—we know the rules.
This opens a massive new market where vendors can reach families, educators, microschools, and ESA participants directly.
Data, Outcomes, and AI
Alex Sarlin:
Do you see a role for ClassWallet in connecting spending data with outcomes?
Jamie Rosenberg:
We’re cautious about causation claims, but the opportunity is real.
On the front end, we’re investing in using data to help families make better decisions – recommendations based on similar learners, popularity, reviews, and usage patterns.
On the back end, we’re working with partners to feed spending data into broader outcome analyses. We don’t claim sole attribution, but we can provide a powerful piece of the puzzle.
AI plays a major role here – both in streamlining compliance and in helping families maximize the impact of each dollar.
Special Needs & the Future of Funding
Alex Sarlin:
How does this all intersect with special needs and neurodivergent learners?
Jamie Rosenberg:
Special needs students were the genesis of school choice. One Texas program we support has distributed $250 million to families with special needs children—many of whom remain in public schools while supplementing with outside services.
This isn’t an either / or future. It’s hybrid. Families can stay in public schools and still access therapy, tutoring, and tools beyond the school day. Programs like ECCA could dramatically expand that model.
Over the next decade, funding will be more blended, flexible, and personalized—especially for students with the greatest needs.
Closing
Alex Sarlin:
That’s a powerful vision. Jamie, it’s clear that financial technology is the linchpin making all of this possible. Thank you for the work you’re doing and for joining us on EdTech Insiders.
Jamie Rosenberg:
Thank you, Alex. It’s been a pleasure.
Read entire transcript here (click "transcript" tag).