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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

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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.