Meet Wayne Cross

My Story

Years in Education. One Recurring Problem.

I grew up knowing school mattered but not always knowing where it was headed. That stayed with me, and it’s a big reason I ended up doing this work.

After finishing my B.A. in English at USD as a McNair Scholar, I went to Penn State for a Master’s in Counselor Education with a focus on career counseling. I worked at their Career Services Center while I was there, sitting down with students and alumni who were trying to make sense of what came next. Some of them were in a good place. A lot of them were not, and had been drifting longer than they realized.

While I was at Penn State, I had a conversation with the head of the career center that stuck with me. He said students who arrive knowing what they want to major in, who have actually thought it through, tend to get a lot more out of their time there. They’re not spending a year and a half figuring out the basics while paying tuition. He had been trying to build something around that idea but it never got off the ground. I kept thinking about it.

Back in San Diego

I moved back to San Diego and spent time in academic advising at CIAT before eventually moving into K–12 education. I’ve been Lead Academic Coach and Resident Teacher at High Tech Elementary and Middle, working with students who have IEPs, multilingual learners, and kids who just need someone in their corner.

That K–12 experience changed how I approach coaching. You learn pretty quickly that every student is different, that the same approach does not work for everyone, and that listening matters a lot more than having the right script.

Why One-on-One

School counselors are stretched thin. Most of them are managing hundreds of students and doing their best with limited time. Career planning in that environment often ends up rushed or generic, and it usually happens too late anyway.

Cross College and Career Readiness exists to give students the individual attention that kind of process actually requires. One person. Real conversation. A result that makes sense for them specifically.