Cassie Oleson

I attribute my success to staying curious and never becoming too comfortable. I believe growth begins when we are willing to ask questions, challenge what we think we know, and step into spaces where we are not yet the expert. I am always asking “why,” looking for a better way, and pushing myself to learn what comes next. That curiosity has carried me from direct student support into the corporate EdTech world and continues to drive my education in psychology, all while keeping me grounded in my purpose of creating meaningful change for children and the systems that support them.

The best career advice I can give is to never let where you are today define where you are capable of going. Stay curious, ask the questions no one else is asking, and be willing to step into opportunities before you feel completely ready. Some of the greatest growth in my career has come from being uncomfortable enough to learn something new and confident enough to trust that I could figure it out. Your career does not have to follow a straight line to be meaningful. Sometimes the unexpected turns are exactly what prepare you for where you are meant to go.

Never underestimate the influence you can have simply by being the person who truly sees a student. Education is demanding and constantly evolving, but the heart of the work remains human connection. Stay curious, remain willing to learn, and don’t become so comfortable with “the way things have always been done” that you stop asking whether there is a better way. Whether you are a teacher, coach, administrator, or support professional, advocate for what students need, even when it requires you to challenge existing systems. You may not always see the impact you make, but the stability, encouragement, and belief you give a child can stay with them long after they leave your classroom.

One of the greatest challenges in education today is balancing increasing demands for documentation, compliance, technology, and data with the reality that educators entered this profession to serve students, not systems. In school-based Medicaid, that challenge is especially important because accurate documentation and effective processes can directly impact the funding available to support Special Education programs and services. I also see tremendous opportunity in using technology more intentionally to simplify those processes, reduce administrative burden, and allow educators to spend more time focused on students. The goal should never be technology for technology’s sake, but creating smarter systems that better support the people doing the work and ultimately the children they serve.

I value integrity, curiosity, empathy, and growth. I believe in doing what is right even when it is not the easiest path, asking difficult questions, and never becoming so comfortable with what I know that I stop being curious about what I don’t.

I try to keep the bigger picture in perspective and remain willing to change course when something is not working. One philosophy I carry with me is, “You weren’t hired to survive the day; you were hired to change it.” To me, success means leaving people, places, and situations better than I found them—and making sure the people I encounter feel seen, heard, and valued.