By Aviv Weiss, Khan Academy Districts team
When Jeff Oldfield transitioned from a 14-year career at Apple into public education, he brought more than industry expertise—he brought a fresh set of questions. Now serving as Executive Director of Innovation and Competitive Advantage at the Riverside County Office of Education (RCOE), Oldfield is partnering with innovative educators across one of California’s largest counties to reimagine learning together.
In this wide-ranging conversation, Jeff talks candidly about the flaws of conventional edtech, his vision for student-centered AI, and how Riverside is using Khanmigo to create more equitable learning environments—especially for students in alternative education and foster care.
Aviv: How did your journey lead you to rethink the role of technology in education?
Jeff: My entire career has been about exploring how technology can disrupt systems. And when I got into education, I noticed a pattern. Most edtech tools answer the question, “How can I do what I’m already doing faster?” That’s efficiency. But I think that’s the wrong question.
The real question should be: “What can I now do that was never possible before?” That’s where real innovation happens. Sadly, not many people are asking that in education.
Aviv: So what stood out about Khan Academy and Khanmigo?
Jeff: We looked at a lot of tools. Most of them rely on teachers to create the space where AI is used. But that reinforces the same limitations we’ve always had—one teacher for 30 kids, trying to differentiate for everyone.
Khanmigo is different. It allows students to directly interact with an AI tutor. It’s not just a tool teachers use to push content. It’s a partner for the learner.
Imagine a kid sitting down with a cardboard rollercoaster project and needing help writing a speech. They open Khanmigo and say, “Can you help me express what I built?” That happened in our schools. And it was transformative. The student would never have written or presented something like that without this support. That’s the magic.
Aviv: What does student-centered really mean in practice?
Jeff: It means removing the artificial barriers of grade levels and seat time. A 10-year-old should be able to do algebra if they’re ready—and not feel weird about it. Similarly, if a student is struggling with foundational math, they should get the help they need without stigma.
Khanmigo supports this because it responds to where the learner is—not where the system says they should be.
Eventually, I’d love to see a toggle in Khan Academy for “true mastery mode”—where content is just content, and age is irrelevant. We’re not quite there yet, but Khan Academy is the closest to this vision.
Aviv: How are you using this in alternative ed?
Jeff: Alternative ed in Riverside is a one-room schoolhouse. Grades 7 through 12 in the same room. It’s not just challenging—it’s impossible to differentiate effectively without technology.
We use project-based learning. So the student isn’t just doing drill-and-kill worksheets. They’re building things, presenting, creating. But they need support along the way. That’s where Khanmigo comes in.
It allows each student to move independently, ask for help when they need it, and feel supported even if a teacher can’t immediately jump in. AI doesn’t get tired. It doesn’t judge. It’s just there to help.
Aviv: What’s the role of the teacher in this model?
Jeff: I think teachers become designers of experiences. It is then less about delivering content, and more about setting up the environment where learning happens.
Think about the best coaches or mentors you’ve had. They weren’t just experts—they were matchmakers. They knew who you were and helped you get into the right situation to grow.
Teachers can do the same—facilitate collaboration, encourage curiosity, guide students toward problems worth solving. If AI can handle the basics, it frees up teachers to spend more time helping kids become the best version of themselves.
Aviv: You talk a lot about starting with the most underserved students.
Jeff: Absolutely. We don’t want to design only for kids who already have everything. Let’s solve for the hardest cases first—students who’ve been expelled, or who don’t have consistent access to schools—and then scale what works.
It’s like universal design. If you build a sidewalk ramp for wheelchairs, you make it easier for strollers and bicycles, too.
That’s why we’re starting with foster youth and community day schools. If Khanmigo can work there, it can work anywhere.
Aviv: What’s next?
Jeff: Our superintendent is focused on giving every kid in Riverside a competitive edge. AI tutoring, differentiated learning, mastery-based progress—those are pieces of that puzzle.
Khanmigo isn’t the whole picture, but it’s a foundational part of it. The work now is to keep growing our cohort of the willing—teachers and principals who are ready to build this new vision with us.
Aviv: You’re also piloting a program for foster youth?
Jeff: Yes. This is one of the projects I’m most excited about. We partnered with Temecula Valley Unified School District to give 22 foster youth an iPad and access to Khanmigo and Khan Academy—nothing else.
Why? Because foster students often move between seven or eight schools a year. Different curriculum. Different textbooks. No consistency.
With Khanmigo, they have a constant companion—a tutor that’s always there, regardless of which district they’re in. If they land in a new math class mid-semester, they can say, “Khanmigo, I don’t know how to do this,” and get the help they need right then.
This is how we bring equity. Not by lowering the bar, but by giving kids tools that travel with them.
Final Thoughts
Riverside’s story is still being written, but what’s clear is that Oldfield and the RCOE team are asking the right questions: not how to do school more efficiently, but how to make it fundamentally better. For every student.
“Learning is a lot more fun when it’s relevant, and you can be curious, and you can go at your own pace,” Jeff says. “It’s not rocket science.”
Riverside County Office of Education is partnered with Khan Academy Districts to drive greater impact at scale.
👉 Get in touch to talk about strategic implementation of AI for learning in your district.
