Episode 256: Rethinking Intervention and Tutoring with Jennifer Sheffield

School leaders everywhere are wrestling with the same challenge:

How do we support students who are behind — without overwhelming teachers or relying on systems that don’t deliver results?

In this episode of Leaning Into Leadership, Darrin Peppard sits down with Jennifer Sheffield, CEO of HeyTutor, for a grounded, practical conversation about what effective tutoring and intervention really look like in today’s schools.

Jennifer brings a unique leadership lens — blending her background in law, governance, and education — to help leaders rethink how tutoring fits into MTSS, Tier 2 and Tier 3 supports, and daily school operations.

In this episode, you’ll hear about:

1. Why “tutoring” means very different things — and what defines high-impact tutoring
2. The biggest barriers schools face when implementing interventions
3. How districts can address the human capital challenge without adding strain to teachers
4. Creative push-in and pull-out models that work in middle and high schools
5. Why relationships and student champions matter as much as curriculum
6. How tutoring can become a pipeline for future educators
7. What it means to lead with purpose, trust, and whole-person leadership

Jennifer also shares a powerful personal story that shapes her leadership philosophy — reminding us that great leadership is ultimately about people, belief, and opportunity.

Learn more:

1. HeyTutor: https://www.heytutor.com
2. Contact Jennifer directly: jennifer@heytutor.com

If you’re a school or district leader searching for intervention strategies that actually move the needle — this conversation will help you think differently.

Episode Sponsors:

This episode is sponsored by digiCOACH — an easy-to-use mobile platform that empowers school leaders to provide teachers with positive, actionable feedback tied to research-based instructional practices, with real-time data to support fidelity and instructional decision-making.

Learn more at digicoach.com (mention the show for special partner pricing)

This episode is also brought to you by HeyTutor - HeyTutor delivers customized, evidence-based, high-dosage Math and ELA tutoring to K–12 school districts nationwide. Their focus is on in-person tutoring, while also offering flexible online options — all tailored to meet diverse student needs and aligned with state standards.

Head over to HeyTutor.com to learn more - tell them you heard about them on the Leaning into Leadership podcast.