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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!

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🎉 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.

Send us a text

Nolan Bushnell is the founder of Atari and Chuck E. Cheese and is widely known as the father of the video game industry. Dr. Leah Hanes is the CEO of ExoDexa, co-author of the ExoDexa Manifesto, and leads the Two Bit Circus Foundation, where she has impacted over 460,000 students through game-based and project-based learning.

💡 5 Things You’ll Learn in This Episode:

1. Why traditional schooling fails students who don’t learn at the “right” pace
2. How game design principles like flow and mastery can transform learning
3. The role AI can play in personalized, no-grades education
4. Why gamification efforts led by academics often fall short
5. What a “perfect school day” could look like in an AI-driven future

✨ Episode Highlights:
[00:03:00] Nolan Bushnell on the throughline from Atari to education reform
[00:05:10] Dr. Leah Hanes on why learning by doing leads to deeper retention
[00:07:52] How AI enables true individualized learning inside ExoDexa
[00:12:16] Nolan on eliminating grades and batch-processing in education
[00:16:58] Why homeschoolers may lead the next wave of education innovation
[00:21:33] The science of “flow” and what makes learning feel addictive
[00:27:51] Leah’s vision for AI tutors, physical activity, and student agency
[00:29:30] Nolan’s radical take on VR, exercise, naps, and brain science in school

😎 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

Join hosts Alex Sarlin, Ben Kornell, Michael Horn and Dhawal Shah as they break down major moves in online learning, AI, and higher education shaping the end of 2025.

✨ Episode Highlights:
[00:00:00] Coursera and Udemy announce a $2.5B all-stock merger forming a 175M-learner platform
[00:00:30] Michael Horn on Coursera’s growing leverage over university partners
[00:02:08] Ben Kornell explores Coursera’s potential to become a global university
[00:05:40] Dhawal Shah explains the financial motivations behind the merger
[00:09:54] Michael Horn compares the deal to the 2U–edX acquisition
[00:11:54] The hosts discuss channel power and aggregation in edtech
[00:16:49] Debate on Coursera’s acquisition strategy and platform future
[00:21:43] Dhawal Shah on why these businesses may perform better as private companies
[00:22:33] Ben Kornell outlines Coursera’s two paths: efficiency or AI-led reinvention
[00:30:24] Gaps in online learning around mentorship and advanced skills
[00:35:29] OpenAI’s latest release and rising competition with Google Gemini
[00:38:55] Why content and IP still matter in the AI era
[00:48:36] Purdue introduces an AI competency requirement for graduates

Plus, special guests:
[00:52:54] Isabelle Hau, Executive Director of the Stanford Accelerator for Learning, on human-centered and social AI in 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 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

2025 was a defining year for AI in education. From rapid adoption to rising educator confidence and growing questions about what comes next.

In Part 1 of our year-end reflections and predictions, Alex Sarlin and Ben Kornell revisit their 2025 reflections and look ahead to what 2026 may bring for EdTech, AI, and the future of learning.

🎙️ Featuring insights from:

• Tom Vander Ark, Founder & CEO, Getting Smart
• Bjorn Billhardt, CEO, Abilitie
• Jacob Kantor, Founder & Chief DODO, JK K12 EDU
• Arman Jaffer, Founder & CEO, Brisk Teaching
• Ian McCullough, Founder & Principal, McCullough Marketing and Management
• Jennifer Carolan, General Partner, Reach Capital
• Andrew Goldman, EVP, HMH Labs

From educator adoption curves to Big Tech’s growing influence, this episode brings together operators, investors, and strategists to unpack what’s shaping education’s next chapter.

😎 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

Rene Kizilcec is an Associate Professor at Cornell University, where he directs the Cornell Future of Learning Lab and leads the National Tutoring Observatory. His research focuses on learning science, AI in education, and the behavioral and computational factors that shape student success. His work has appeared in Science, PNAS, and other top journals.

💡 5 Things You’ll Learn in This Episode

1. How the National Tutoring Observatory is building the largest dataset of real tutoring interactions.
2. What specific “tutoring moves” actually drive learning outcomes.
3. How AI models can be trained to use stronger pedagogical strategies.
4. Why education needs real benchmarks for measuring teaching quality in AI.
5. How simulation-based learning is transforming medical and language training at Cornell.

✨ Episode Highlights
[00:00:00] Rene on aligning AI study tools with real pedagogy.
[00:02:33] Lessons from early MOOC research on equity and completion.
[00:05:58] How motivation and belonging interventions improved outcomes.
[00:10:57] The mission and structure of the National Tutoring Observatory.
[00:13:01] Why tutoring works—and why we haven’t known which moves matter.
[00:18:28] Tools for identifying tutoring moves across huge datasets.
[00:20:00] Using tutoring data to influence hyperscalers and AI product design.
[00:22:37] The need for robust benchmarks for AI tutoring quality.
[00:27:42] Why great tutors ask questions instead of giving answers.
[00:31:03] How tutoring data can improve AI models while preserving privacy.
[00:34:34] How tutoring providers can join the NTO consortium.
[00:37:16] Simulation-based learning with MedSimAI and Chitter Chatter.
[00:41:34] How AI-assisted development accelerates EdTech innovation.

😎 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.

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

Join hosts Alex Sarlin, Ben Wallerstein, and Matt Tower for Week in Edtech, exploring OpenAI’s teacher certifications, kids’ online safety legislation, early literacy declines, college admissions pressures, and what remains irreplaceable in education as AI advances.

✨ Episode Highlights
[00:03:00] OpenAI launches teacher certifications, expanding into K–12
[00:05:00] Big Tech credentials raise control and gatekeeping concerns
[00:07:55] Doubts emerge around certifying AI pedagogy
[00:12:40] Google and OpenAI intensify competition for schools
[00:14:15] Congress advances online safety bills affecting edtech
[00:19:15] COPPA changes threaten AI personalization
[00:24:05] Parent reading declines deepen literacy gaps
[00:26:45] Early childhood remains underfunded despite high impact
[00:31:15] College admissions lean further into yield management
[00:33:10] AI reshapes admissions essay review
[00:36:20] Trust in higher education continues to fall
[00:40:40] Education systems face pressure to adapt

Plus, special guests:
[00:45:30] Maya Bialik, Founder of QuestionWell, and Peter Nilsson, Founder of Athena Lab, on their book Irreplaceable: How AI Changes Everything (and Nothing) in Teaching and Learning

[01:11:16] Emily Gill, Co-Founder & COO of LEVRA, on AI simulations for human skills development

😎 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 person

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.