Edtech Insiders

Redefining School Discipline with Technology and Empathy with Nathan Maynard of HighFive


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Roosh X is an investment arm of Roosh Investment Group.

Nathan Maynard is the CEO and Founder of HighFive, a company using mobile technology to foster connected school communities and reduce recidivism for negative classroom behaviors. With over 11 years of experience as a youth worker, teacher, and school administrator, Nathan co-authored the best-selling book "Hacking School Discipline," and is a global thought leader in reimagining discipline practices in education.

💡 5 Things You’ll Learn in This Episode:

  • How Highfive uses technology and empathy to reshape school discipline.
  • The importance of creating a sense of belonging to reduce negative behaviors.
  • Nathan's journey from youth worker to edtech entrepreneur and thought leader.
  • The impact of AI on real-time behavioral interventions in schools.
  • How Highfive is expanding its reach across the U.S. with new partnerships and funding.

✨ Episode Highlights:

[00:01:46] Introduction to Nathan Maynard and Highfive’s mission to transform school discipline.
[00:03:34] Building connected school communities to reduce negative behaviors.
[00:05:43] How real-time technology supports teachers in managing discipline
[00:08:13] From "Hacking School Discipline" to scaling Highfive’s impact
[00:21:26] Using AI to address systemic bias and improve behavioral insights
[00:24:34] Highfive’s expansion strategy across key U.S. states.
[00:27:55] Partnership with Roosh X to support growth and mental health initiatives.
[00:34:22] Promoting positive behavior with Highfive's virtual "high fives" system.

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Tuck Advisors was founded by entrepreneurs who built and sold their own companies. Frustrated by other M&A firms, they created the one they wished they could have hired, but couldn’t find. One who understands what matters to founders, and whose northstar KPI is % of deals closed. If you’re thinking of selling your EdTech company or buying one, contact Tuck Advisors now!

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.

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Edtech InsidersBy Alex Sarlin and Ben Kornell

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