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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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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 30 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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