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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

1. Why education funding breakdowns are often about infrastructure, not intent
2. How ClassWallet replaced reimbursement with real-time, compliant digital wallets
3. What it takes to run ESA and school choice programs at scale
4. How empowering teachers and families unlocks creativity and efficiency
5. 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.

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Henry Motte de la Motte is the Founder and CEO of EDGE Tutor, a global tutor outsourcing company supporting over 50 leading education and training organizations. Under his leadership, EDGE Tutor has scaled to 1,000+ teachers across 30+ countries, delivering millions of live tutoring sessions with a focus on quality, reliability, and human-centered learning.

💡 5 Things You’ll Learn in This Episode:

1. Why tutor reliability matters more than most EdTech's realize
2. How outsourcing enables high-quality tutoring at global scale
3. What makes matching tutors to learners actually work
4. How platforms use external tutor supply to handle peak demand
5. Why AI works best as support and not a replacement for human tutors

✨ Episode Highlights:
[00:02:23] EDGE Tutor as behind-the-scenes tutoring infrastructure
[00:03:32] BPO lessons applied to education
[00:06:18] Reliability as the core of learning quality
[00:09:46] Cultural training across markets
[00:13:08] Why EDGE Tutor chose white-label over brand
[00:16:21] Diversifying tutor supply to reduce risk
[00:21:47] How COVID reshaped online tutoring
[00:25:14] A pragmatic take on AI tutoring
[00:30:00] The rise of hybrid human + AI models
[00:42:31] Consolidation coming to edtech

😎 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.

Send us a text

In Part 2 of our year-end reflections, Alex speaks with educators, founders, investors, and platform leaders about what 2026 may bring for AI and learning at scale.

🎙️ Featuring insights from:

• Shantanu Sinha, Director of Education, Google for Education
• Katie Kurtz, Managing Director & Global Head of Youth & Learning, YouTube
• Amit Patel, Co-Founder & Managing Partner, Owl Ventures
• Jomayra Herrera, Partner, Reach Capital
• Jean-Claude Brizard, President & CEO, Digital Promise
• Sunil Gunderia, Co-Founder & CEO, Stealth
• Sofia Fenichell, Founder & CEO, Study Hall.AI
• Soren Rosier, Founder, PeerTeach
• Dan Carroll, Co-Founder, Clever
• Juliette Reid, Director of Market Research, Reading Horizons
• Amanda Bickerstaff, CEO, AI for Education

😎 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 hit

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.