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Tammy Wincup has served for over 25 years as a business executive at the intersection of technology and education. Tammy is currently the Chief Executive Officer of Securly, the leading digital safety and wellness company serving over 22,000 K-12 schools globally to keep students safe, secure, and ready to learn.

Before Securly, Tammy was a partner at Rethink Education, an impact venture fund investing in global education technology. For almost a decade, Tammy was the Chief Operating Officer (COO) at EVERFI, a leading education technology company. She also served as the President of Revolution Foods and the Founding President of Protocol, a media company covering the intersection of technology and policy.

💡 5 Things You’ll Learn in This Episode:

1. Why Securly sees digital safety as a shared responsibility between schools, families, and communities
2. How schools can implement AI without compromising student privacy
3. What real-time data from 40% of U.S. schools reveals about device use, social media, and AI trends
4. Why human-in-the-loop systems matter for student mental health monitoring
5. The emerging role of CTOs as strategy leaders in K-12 districts

✨ Episode Highlights:

[00:02:29] Tammy Wincup explains Securly’s mission to protect students across digital environments
[00:04:42] How classroom management and device use connect to digital wellness
[00:09:20] Phone bans lead to 30% spikes in school device usage
[00:14:16] What Securly learns from 40% of U.S. K-12 schools
[00:16:08] Why Tammy urges districts: “Don’t block AI — manage it transparently”
[00:24:31] Using anonymous trends to flag real student wellness risks
[00:34:03] How AI puts school tech leaders back in strategic roles
[00:46:20] Tammy’s go-to sources for spotting big edtech shifts

😎 Stay updated with Edtech Insiders!

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🎉 Presenting Sponsor/s:

This season of Edtech Insiders is brought to you by Starbridge. 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 once again brought to you by Tuck Advisors, the M&A firm for EdTech companies. Run by serial entrepreneurs with over 25 years of experience founding, investing in, and selling companies, Tuck believes you deserve M&A advisors who work as hard as you do.

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Join hosts Alex Sarlin and Ben Kornell as they explore the latest developments in education technology, from AI showdowns to immersive learning pilots and funding updates.

✨ Episode Highlights:

[00:02:00] OpenAI announces $28M K-12 AI training initiative with AFT, UFT, and Microsoft
[00:04:34] Gallup-Walton poll reveals 68% of teachers lack AI training despite high usage
[00:07:11] OpenAI takes a bottom-up approach as teachers criticize Google’s AI rollout
[00:23:41] Meta forms Superintelligence Labs, aggressively hiring AI talent across the industry
[00:36:17] Senate blocks AI regulation ban, states retain power to legislate AI in education
[00:37:31] Higher Ground Education files for Chapter 11 bankruptcy, prompting edtech funding debate
[00:42:05] Honor Education raises $38M to enhance asynchronous social learning
[00:42:45] Teaching Lab merges with Relay Graduate School of Education to scale AI-aligned PD

Plus, special guests:

[00:44:17] Josh Reibel, CEO of Dreamscape Learn and Dr. Jennifer Cruz, Superintendent of the Pendergast Elementary School District discuss VR and immersive learning with Dreamscape Learn
[01:46:15] Eduaide.Ai founders Thomas Thompson and Thomas Hummel on empowering teacherpreneurs with AI

😎 Stay updated with Edtech Insiders!

• Follow our Podcast on:
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• Sign up for the Edtech Insiders newsletter.
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🎉 Presenting Sponsor/s:

This season of Edtech Insiders is brought to you by Starbridge. 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 once again brought to you by Tuck Advisors, the M&A firm for EdTech companies. Run by serial entrepreneurs with over 25 years of experience founding, investing in, and selling companies, Tuck believes you deserve M&A advisors who work as hard as you do.

Send us a text

In this special episode, we speak with the founder of Edthena and five outstanding educators who were honored as 2025 Teacher Leader Impact Award winners. Each guest shares how they’re shaping the future of professional learning, using technology in smart and supportive ways, and leading from the classroom and beyond.

💡 5 Things You’ll Learn in This Episode:

1. Why teacher leadership goes beyond classroom walls.
2. How video coaching and AI are transforming PD.
3. What real educators want from edtech tools.
4. Creative ways teachers are building community and sharing practice.
5. How teachers use tech to boost resilience, reading, and student engagement.

✨ Episode Highlights:

[00:01:22] Adam Geller, Founder of Edthena, on designing teacher-first technology
[00:10:06] Why Edthena launched the Teacher Leader Impact Awards

Teacher Interviews:

[00:17:54] Betsy Springer, Instructional Coach at Gull Lake Virtual Partnership, on virtual instructional coaching, teacher visibility, and learning walks
[00:29:08] Wavell Blades, Deputy Head of British International School of New York, on how his school builds belonging and tracks student citizenship through tech
[00:38:49] LeeAnn Caradine, Teacher at Scandia Elementary in Travis Unified School District, on introducing coding, typing, and 3D printing to young learners
[00:50:44] Davina Lyons, Educator & Founder of Rising Resilience, on supporting student and teacher resilience post-pandemic
[01:06:22] Qingyan Kang, 3rd Grade Mandarin Teacher at Broadway Elementary in Venice, on leading in a bilingual immersion program with cross-cultural collaboration

😎 Stay updated with Edtech Insiders!

• Follow our Podcast on:
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• Sign up for the Edtech Insiders newsletter.
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🎉 Presenting Sponsor/s:

This season of Edtech Insiders is brought to you by Starbridge. 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 once again brought to you by Tuck Advisors, the M&A firm for EdTech companies. Run by serial entrepreneurs with over 25 years of experience founding, investing in, and selling companies, Tuck believes you deserve M&A advisors who work as hard as you do.

Send us a text

Sam Whitaker is the Senior Director of Social Impact and Institutional Development at StudyFetch, an all-encompassing AI learning platform for students. His primary focuses are bringing advanced AI education to underserved communities around the world and developing safe and responsible K-12 AI solutions.

💡 5 Things You’ll Learn in This Episode:

1. How StudyFetch is redefining AI as a learning tool, not a shortcut.
2. The story behind Sparky, the AI tutor designed for real engagement.
3. Why AI literacy is becoming essential for K-12 students.
4. What a million student interactions reveal about how AI is used for learning.
5. How StudyFetch is expanding access to AI education from North Philadelphia to Uganda.

✨ Episode Highlights:

[00:03:08] What makes StudyFetch different from generic chatbots
[00:06:47] Sam on why AI literacy should be taught like reading and math
[00:09:09] Why AI must be implemented despite hesitations: “If we wait, we lose.”
[00:12:32] Explaining the difference between using AI to learn and learning AI itself
[00:15:29] A third-grade use case for prompting skills with Sparky the tutor
[00:23:46] The tension between growth and staying true to learning principles
[00:32:55] The big reveal: findings from over a million StudyFetch conversations
[00:38:52] Why students prefer step-by-step help in math and STEM subjects
[00:42:34] On making AI a true equalizer in education, not a divider

😎 Stay updated with Edtech Insiders!

• Follow our Podcast on:
  • Apple Podcasts
  • Spotify
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• Sign up for the Edtech Insiders newsletter.
• Follow Edtech Insiders on LinkedIn!

🎉 Presenting Sponsor/s:

This season of Edtech Insiders is brought to you by Starbridge. 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 once again brought to you by Tuck Advisors, the M&A firm for EdTech companies. Run by serial entrepreneurs with over 25 years of experience founding, investing in, and selling companies, Tuck believes you deserve M&A advisors who work as hard as you do.

Send us a text

Join hosts Alex Sarlin and Ben Kornell with guest Jacob Kantor as they explore a transformative Week-in-Edtech, from Google’s AI-powered classroom revolution to major political shifts affecting schools nationwide.

Episode Highlights:

[00:03:17] Google launches 50 AI tools for educators through Classroom and Gemini
[00:05:47] Startup funding threatened as Google expands free AI features
[00:13:41] Google solidifies K-12 dominance, pushing out AI competitors
[00:24:51] OpenAI and Microsoft fund new AI training hub for 400,000 teachers
[00:33:22] Survey finds 60% of teachers using AI, saving nearly 6 hours per week
[00:36:22] Federal government freezes $6B in school funding, including EL programs
[00:38:17] ICE raids linked to 30% rise in school absences among Latino students
[00:43:32] Families turning to private edtech as school trust declines
[00:46:49] ISTE highlights include Amplify, Brisk, Quizziz rebrand, Meta’s school mode
[00:50:34] Edtech Insiders WhatsApp group emerges as top source for breaking news

Plus, special guests:

[00:51:36] Matt Dalio, Founder of Endless Studios on teaching real-world skills through student-designed video games
[00:53:56] Anne Trumbore, author of The Teacher in the Machine, on AI, learning platforms, and the future of teaching

😎 Stay updated with Edtech Insiders!

• Follow our Podcast on:
  • Apple Podcasts
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• Sign up for the Edtech Insiders newsletter.
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🎉 Presenting Sponsor/s:

This season of Edtech Insiders is brought to you by Starbridge. 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 once again brought to you by Tuck Advisors, the M&A firm for EdTech companies. Run by serial entrepreneurs with over 25 years of experience founding, investing in, and selling companies, Tuck believes you deserve M&A advisors who work as hard as you do.

Send us a text

Matt Miller is the CEO and Co-Founder of OKO Labs, an innovative EdTech company developing human-centric, pro-social AI to power collaborative learning in K-12 classrooms. With a background as CTO and VP of Labs at Amplify Education and VP of Product at Flatiron School, Matt brings deep technical expertise and a passion for leveraging technology to solve real-world educational challenges. Holding BS and MS degrees in Computer Science and Intelligent Systems from Columbia University, Matt co-founded OKO in 2020 to address the critical need for scalable, engaging, and equitable small-group learning solutions, starting with a focus on math intervention. He leads OKO's mission to foster not only academic growth but also essential skills like teamwork and communication, driven by a commitment to evidence-based practices and rigorous R&D.

💡 5 Things You’ll Learn in This Episode:

1. Why small group learning is a critical—and underserved—area in K-12 education
2. How OKO uses AI to foster real-time collaboration and discourse among students
3. The benefits of integrating AI to support, not replace, educators
4. How rigorous research and efficacy studies shaped OKO’s product design
5. Insights into OKO’s 30x classroom growth and founder-led sales strategy

✨ Episode Highlights:

[00:03:07] Origin of OKO: Solving the challenge of small group instruction
[00:05:17] Using AI bots to facilitate collaborative student learning
[00:10:18] What a typical AI-powered OKO math session looks like
[00:14:47] Research partnership with WestEd shows strong early results
[00:19:42] Making efficacy a sales advantage in founder-led growth
[00:25:59] Combining grant funding and equity to scale responsibly
[00:31:37] Defining a new edtech category: small group AI instruction
[00:36:22] Future plans for subject expansion and deeper SEL integration
[00:40:14] Vision for AI-enabled, pro-social, human-centered classrooms

😎 Stay updated with Edtech Insiders!

• Follow our Podcast on:
  • Apple Podcasts
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• Sign up for the Edtech Insiders newsletter.
• Follow Edtech Insiders on LinkedIn!

🎉 Presenting Sponsor/s:

This season of Edtech Insiders is brought to you by Starbridge. 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 once again brought to you by Tuck Advisors, the M&A firm for EdTech companies. Run by serial entrepreneurs with over 25 years of experience founding, investing in, and selling companies, Tuck believes you deserve M&A advisors who work as hard as you do.

Send us a text

Join hosts Alex Sarlin and Ben Kornell for a thought-provoking summer edition of Week in Edtech, featuring headline debates on AI in education, a rare look into PBS KIDS’ funding crisis, and grassroots innovation in ocean learning from Ecuador.

✨ Episode Highlights:

[00:03:16] MIT study raises alarms about AI's impact on student thinking
[00:07:42] AI cheating scandal hits national debate championships
[00:12:33] Teachers vent frustration as AI disrupts classroom dynamics
[00:14:45] Educators face a crossroads: ban AI or embrace it as a teaching tool

Plus, special guests:

[00:19:09] Sara DeWitt, SVP & General Manager of PBS KIDS, on funding cuts, educational media, and AI experiments in public broadcasting
[00:41:38] José Francisco Ochoa Ordóñez, Co-founder of Academia del Oceano, on democratizing ocean education through hybrid EdTech in Latin America

😎 Stay updated with Edtech Insiders!

• Follow our Podcast on:
  • Apple Podcasts
  • Spotify
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• Sign up for the Edtech Insiders newsletter.
• Follow Edtech Insiders on LinkedIn!

🎉 Presenting Sponsor/s:

This season of Edtech Insiders is brought to you by Starbridge. 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 once again brought to you by Tuck Advisors, the M&A firm for EdTech companies. Run by serial entrepreneurs with over 25 years of experience founding, investing in, and selling companies, Tuck believes you deserve M&A advisors who work as hard as you do.

Send us a text

Jerome Pesenti is the founder of Sizzle AI, an AI-for-learning company whose mission is to make learning amazing for everyone. Jerome has worked in AI for the past 25 years, including as VP of AI at Meta, co-CEO of BenevolentAI, VP at IBM Watson, and co-founder of Vivisimo (sold to IBM).

💡 5 Things You’ll Learn in This Episode:

1. How Sizzle AI uses bite-sized, adaptive learning to help students study more effectively.
2. Why Jerome left big tech to tackle educational challenges with AI.
3. The evolving role of homework and assessments in the age of generative AI.
4. How AI can personalize learning paths and study plans for individual learners.
5. The future vision for AI as a lifelong learning companion across school, work, and personal interests.

✨ Episode Highlights:

[00:02:21] Sizzle AI turns study guides into personalized learning paths.
[00:03:10] Jerome shares why he left Meta to focus on AI for learning.
[00:05:45] Test prep mode boosts readiness with smart study plans.
[00:06:51] Students love Sizzle for making hard content manageable.
[00:08:18] Gamification features are coming soon to enhance engagement.
[00:09:16] Why Sizzle chose a direct-to-learner approach over schools.
[00:11:00] AI shows steps, not just answers, to promote real learning.
[00:14:36] AI can assess student readiness, not just complete tasks.
[00:17:29] Future of testing: both AI-assisted and AI-free formats.
[00:20:14] Sizzle already supports learning beyond the classroom.
[00:23:04] The role of personality in AI study companions.
[00:25:03] Using data to drive learning science at scale.

😎 Stay updated with Edtech Insiders!

• Follow our Podcast on:
  • Apple Podcasts
  • Spotify
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• Sign up for the Edtech Insiders newsletter.
• Follow Edtech Insiders on LinkedIn!

🎉 Presenting Sponsor/s:

This season of Edtech Insiders is brought to you by Starbridge. 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 once again brought to you by Tuck Advisors, the M&A firm for EdTech companies. Run by serial entrepreneurs with over 25 years of experience founding, investing in, and selling companies, Tuck believes you deserve M&A advisors who work as hard as you do.