Building Stronger School Communities Through Enrollment and Retention with Benjamin Welbourn

In this episode of Chalk and Code, host Theron Davis is joined by Benjamin Welbourn, CEO of Schola, a Phoenix-based edtech platform helping families find the schools that fit them best. What began as a startup helping parents navigate school options has evolved into a full ecosystem, streamlining enrollment, managing community programs, and even using AI to help schools build stronger relationships with families.Ben shares his own experience as a learner who didn’t feel at home in traditional classrooms, and how that journey shaped his commitment to personalized, student-centered education. From hiking the Appalachian Trail to launching Virto Education and now leading Schola, his story is one of building bridges between students, systems, and meaningful outcomes.This conversation explores how school choice, AI, community engagement, and human connection intersect and what it takes to make education feel less like a system and more like a fit.Key Moments03:47 Global College Pathway Expansion08:24 Expanding Enrollment Through Extracurriculars11:23 Improving School Enrollment Practices14:28 Family School Engagement Strategy20:13 Prioritizing Psychological Safety in Schools22:08 Enrollment Challenges and Cycles24:30 School Consolidation Necessity28:57 "Real-Time School Engagement Insights"32:55 Parent-School Connection Challenges37:07 AI-Powered School Program Recommendations39:31 Ed Tech Challenges and Growth41:03 Esser Funds' Aftermath on Schools47:31 Substance Over AI HypeWhy You’ll Love This EpisodeYou’ll hear how Benjamin and the team at Schola are flipping the script on traditional K–12 marketing by helping schools build trust, communicate value, and become hubs for their communities. If you're in education, product, policy, or just want to know how schools can thrive in an era of rapid change, this episode offers a playbook for putting families first and using data, tech, and empathy to make it happen.You’ll walk away with:A fresh perspective on school choice and community engagementReal examples of how Schola helps schools attract and retain the right studentsInsights into how AI can amplify, not replace, human relationships in educationLessons on navigating today’s rapidly shifting education landscape with integrityConnect with Benjamin WelbournLinkedIn: https://www.linkedin.com/in/benwelbourn  Breshna: https://home.schola.com/ Connect with UsCompany’s LinkedIn: https://www.linkedin.com/company/flexion-incCompany Website: https://flexion.us/If this conversation sparked a new idea or challenged your assumptions, share this episode with a colleague and subscribe for more thoughtful discussions at the intersection of learning, leadership, and educational technology.Join us next time on Chalk and Code, where the science of learning meets modern technology.