Rethinking School for the Age of AI with Jennifer Womble

In this episode of The Boyz of EdTech, Rick Fernandez, Jacob Kantor, and Jeff Piontek sit down with Jennifer Womble, Conference Chair and EdTech Advisor for the Future of Education Technology Conference (FETC), for a wide-ranging conversation about where education is headed and what schools need to rethink along the way. Jennifer shares her unconventional path into education, from studying economics and criminology to becoming a teacher, working at the state and national levels, and developing a broad view of the education ecosystem.

The conversation explores a fundamental question: What is school actually preparing students for? Jennifer argues that education cannot simply train students for jobs that may look completely different in the future. Schools need to develop lifelong learners who can think critically, solve problems, communicate, adapt, and understand their own learning. As AI accelerates change, those durable human skills, along with curiosity, metacognition, autonomy, and agency, become even more important.

Jennifer also explains why successful technology adoption starts with community, strategy, and trust. Rather than beginning with a product, districts should involve families, educators, businesses, and other stakeholders in defining what learning should look like. The group discusses cybersecurity, responsible AI implementation, outcomes-based contracting, parent communication, and why EdTech companies need to listen before they sell. Jennifer emphasizes that AI should amplify strong curriculum and pedagogy rather than become the foundation itself.

The conversation then turns toward what comes next, from AI-powered creativity and immersive learning to CTE, esports, cybersecurity, accessibility, and new approaches to assessment. Jennifer shares what FETC is seeing across districts and why some of the most exciting innovation is happening in career and technical education. The episode closes with a vision of schools that combine competency-based learning, multiple learning environments, human connection, and emerging technology while keeping curiosity, belonging, and student growth at the center.

Connect with the Boyz
Rick Fernandez: https://www.linkedin.com/in/dr....-rick-fernandez-4069
Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/
Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/
Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/
Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/

Key Moments

03:54 How a nontraditional background shaped Jennifer’s perspective

07:52 Rethinking the purpose of school and preparing lifelong learners

15:11 Why AI is forcing districts to examine deeper systemic challenges

17:45 Building AI strategy with community involvement from the start

22:09 Why EdTech companies need honest district feedback and co-building

27:42 Trust, listening, and stronger partnerships between districts and vendors

30:22 The risks and realities of outcomes-based contracting

38:02 Rethinking how districts communicate learning with families

40:54 Teaching AI wisdom, critical thinking, and responsible use

46:45 How AI can expand creativity and student problem-solving

50:20 What FETC is seeing across AI, CTE, immersive learning, and cybersecurity

56:21 Why CTE is becoming one of the most innovative areas in education

58:17 Integrating AI into authentic, project-based learning experiences

01:03:20 Competency-based learning and the future redesign of school

Connect with Guest
Jennifer Womble: https://www.linkedin.com/in/jennwomble

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38