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Sam Olivieri is the CEO of and has spent more than two decades expanding educational opportunity through leadership roles at GreatSchools, Entangled Solutions, and Guild Education. Daniel Halper is Co-Founder of Step Up Tutoring and leads Step Up AI Labs, where he develops AI-powered tools that help novice tutors deliver high-impact instruction at scale.

💡 5 Things You’ll Learn in This Episode:

1. Why Step Up Tutoring believes relationships and not AI alone drive student success
2. How AI can coach and support tutors instead of replacing them
3. The opportunity to transform federal work-study into a national tutoring corps
4. How Step Up uses AI to align tutoring with district curricula like Eureka Math
5. What it takes to scale high-impact tutoring affordably across the country

✨ Episode Highlights:
[00:03:15] Sam Olivieri explains why tutoring remains one of education’s most evidence-based interventions.
[00:07:00] Daniel Halper shares how Step Up Tutoring launched during COVID as a grassroots volunteer movement.
[00:09:48] Daniel discusses why AI should support tutors rather than replace human relationships in learning.
[00:11:36] Sam outlines how federal work-study funding could help build a national tutoring corps.
[00:14:41] Daniel breaks down how Step Up’s AI tools support tutors before, during, and after sessions.
[00:18:52] Sam explains how AI evolved from tutor feedback into curriculum alignment and student mastery assessment.
[00:21:20] Step Up Tutoring shares its vision of providing every child in need with an effective human tutor supported by AI.

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