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

Send us Fan MailSam 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. 😎 Stay updated with Edtech Insiders! Follow us on our podcast, newsletter & LinkedIn here.🎉 Presenting Sponsor/s: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. 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. 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.