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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:

Why Step Up Tutoring believes relationships and not AI alone drive student success
How AI can coach and support tutors instead of replacing them
The opportunity to transform federal work-study into a national tutoring corps
How Step Up uses AI to align tutoring with district curricula like Eureka Math
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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The Future of Tutoring Is Human + AI: Sam Olivieri & Daniel Halper of Step Up Tutoring

Edtech Insiders

The Future of Tutoring Is Human + AI: Sam Olivieri & Daniel Halper of Step Up Tutoring