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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:
  • Apple Podcasts
  • Spotify
  • Amazon Music
• 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

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:
  • Apple Podcasts
  • Spotify
  • Amazon Music
• 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.