Preparing Every Classroom for Career Success

Jarrad Grandy, Executive Director of Student, Oakland Schools

Jarrad Grandy is a visionary education leader, driving countywide career readiness initiatives impacting over 28 local districts. He holds a Master’s in Educational Leadership from Grand Valley State University and brings expertise in teaching, program design, career readiness and STEM education. With his extensive educational background, Grandy bridges the gap between employers, educators, and students to create impactful, real-world learning experiences that prepare youth for meaningful careers.

Moving into Career Tech Education

When I reflect on my career in educational leadership, I often trace it back to my beginnings as a social studies teacher. My transition into administration came through my work in career and technical education (CTE), where I realized the importance of making learning relevant. Over the years, my role has expanded well beyond CTE, but that foundation still influences everything I do today.

One key thing I have learned on this journey is that all students, regardless of their zip code, socioeconomic status, race, or gender, benefit when their education is tied to something meaningful. I believe students learn best when lessons are connected to real-world challenges, and it's up to leaders like us to ensure they make the greatest impact. That’s where relevance becomes a powerful driver of engagement and success.

The way I think about student learning and equity wasn’t formed all at once. It gradually took shape as I stepped out of general education and immersed myself in CTE. I came to see career readiness as a fundamental right for every student. But it's not just about finding a job; it's about helping students discover what they're good at, what they enjoy and whether there’s a demand for those skills in the world.

Leadership, Focus and Service

As Executive Director, ensuring student success and wellbeing means building systems that are both strategic and inclusive. None of this work happens in isolation; it requires aligned leadership at every level, from the superintendent and fellow cabinet members to direct reports. Particularly, it needs clarity of purpose and the discipline to say no to initiatives that dilute focus. People in education are often inclined to say yes, but I stand firm in the belief that true impact comes from focusing on what is meaningful.

That's precisely what Oakland Schools embodies, staying focused on what matters most and setting aside the rest. As part of the team, I see how it supports the entire county, not just a single district or school. That means listening carefully, analyzing data and responding to the actual needs of districts rather than relying on assumptions. It involves establishing measurable goals, fostering open communication and continually reassessing whether we are solving the right problems.

A considerable part of our strategy involves community partnerships. Connecting students with employers and industry leaders isn't just beneficial—it's essential. We build relationships with trade associations, workforce development groups and other backbone organizations to drive collaboration and strengthen the talent pipeline.

“I believe students learn best when lessons are tied to real-world challenges, and it’s up to leaders like us to ensure they make the greatest impact”

That said, the most valuable contribution employers can offer is their time, expertise and willingness to engage. We facilitate experiences that bring employers into schools and take students and educators into workplaces. Whether it’s through job shadowing, field trips, guest speakers or immersive projects, these connections only become meaningful when they are intentionally tied back to instruction.

The Scale Dilemma

At Oakland Schools, we place career readiness at the core of every classroom from the very beginning. This approach requires a shift in how we teach, where real-world problems, industry challenges and purpose-driven instruction guide the learning experience. It’s a major pedagogical shift, and we are embracing it more deeply than ever.

Of course, coordinating equitable services across a diverse set of districts presents its challenges. The greatest of these is scale. It's one thing to implement an initiative in a single classroom or school, but bringing that level of excellence to an entire county is a different challenge altogether. As a service agency, our influence is often persuasive rather than directive— we can guide, support and resource our districts, but not mandate their actions. But through it all, we remain committed to continuous improvement, ensuring every student gains the skills and experiences needed for career readiness and future success.

A Call for Change

If I could offer one piece of advice to those who want to lead in student services, it would be to keep the focus on the classroom. They must understand what’s happening in classrooms and analyze how often relevance is truly present in what students are learning. If it’s not happening consistently, then it’s time to reformulate their instructional strategy.

Lasting change depends on adults who are willing to evolve at a pace that meets students’ needs, because they can’t afford to wait. At its core, creating a relevant, inclusive and careerconnected education system means building a future where students don’t just pass through school—they find purpose in it. That, I believe, is the heart of equity.