In the very first episode of Autonome, host Fran Kenton, Founder and Creator of Autonome, sits down with Jarrad Grandy, Executive Director of Student Services at Oakland Schools. Serving more than 176,000 students across 28 districts, Jarrad shares how his journey from teacher to administrator to countywide leader shaped his mission to help every student become career ready.
Fran and Jarrad discuss how students can explore three essential questions: What are you good at? What do you like to do? Is someone willing to pay you for it? They also talk about the challenge of moving from isolated success to scalable systems, and how Oakland Schools is building a first-of-its-kind K–12 nanotech, AI, and synthetic biology lab designed to make learning relevant to the real world.
Key Moments
01:18 Jarrad’s path from student to teacher to district leader
03:03 Why early career challenges pushed him toward leadership
04:16 The conversation that shifted him from building work to district work
05:21 How family guidance influenced his leadership decisions
06:15 The biggest challenge in education: scaling excellence
07:04 Why making every student career ready is his core mission
08:28 Moving from pockets of excellence to consistent systems
09:03 Using clear, measurable targets to drive districtwide progress
11:11 Funding and supports available for district experiences
12:48 Awareness, exploration, and preparation as a continuous cycle
14:24 Why educators need industry experiences to teach real relevance
18:09 Teaching human skills like communication and collaboration
20:12 Using real problems instead of symbolic examples
23:02 What systems must shift to ensure true career readiness
Why You’ll Love This Episode
This episode gives a practical and clear look at what career readiness should mean today. Jarrad shares a simple but powerful framework that blends relevance, industry alignment, and repeated student experiences so districts can help learners connect their strengths to real opportunities. His examples show how to make learning stick and how to redesign experiences so students can understand what is possible for their futures.
You will also hear a thoughtful perspective on systems change. Jarrad explains how teacher externships, industry partnerships, and meaningful curriculum shifts can help districts scale what works. Whether you are a teacher, principal, or district leader, you will find concrete steps to elevate student agency and future readiness.
Connect with Jarrad Grandy | Executive Director of Student Services, Oakland Schools
Connect with Fran Kenton and Autonome
About Autonome
Autonome is the podcast where district leaders share practical, scalable ways to build students’ foundational life skills—wellbeing, identity and purpose, relationships, and executive function—so they can manage life today and be ready for what’s next.
If you enjoyed this episode, subscribe to Autonome for more conversations with leaders shaping the future of student success.