Alumni Focus - Brittany Oberstadt ('09)

Brittany Oberstadt (’09) shares her memories of SCLA and how the unique cross-cultural context prepared her for the technical and creative dimensions of her career.  While working in the cybersecurity industry and performing professionally with the Mystery Café and as a member of the St. Paul Saints Baseball Entertainment team, she shares joy, curiosity, and humor while pursuing adventure and traveling the world. 

What are some of your favorite memories from your time at St. Croix?
Were there any teachers or staff who had a big impact on you?
Were you involved in any extracurricular activities that helped shape who you are today?

Some of my favorite memories from my time at St. Croix are tied to the wide range of extracurricular opportunities I was able to experience. I really did try just about everything. I played soccer with Pastor Huebner and joined the basketball team, but soon realized I was mostly in it for the social aspect. That’s when I switched to being a team manager, which required significantly less conditioning, but was just as much fun being part of the group.

Performing in children’s theatre with Mr. Hanson and participating in one-acts with Mr. Strehlow sparked my love for acting. They taught me how to share joy through humor and whimsy, lessons that have stayed with me ever since.

Music also became a lifelong passion thanks to my experiences singing with the Croixaliers, performing in musicals, and band with Mr. Pufahl and Mr. Kassulke. Additionally, I got my start in leadership through student council, which helped me grow in confidence and responsibility.

How did your experience at St. Croix shape your understanding of international cultures?

Building friendships with international students deepened my appreciation for the varying ways people live, think, and connect. Those experiences encouraged me to listen without assumptions and to value each perspective for its uniqueness. I’ve learned to approach cultural differences with curiosity and respect, seeing them as opportunities to broaden my own understanding rather than as points of comparison. This mindset continues to inspire my passion for traveling and exploring new places. Whether I am in Taiwan, Iceland, or Peru, I seek to learn from the rich diversity our world offers.

What path did you take after graduating? 

I never had a single, clear vision of what I wanted to “be” when I grew up. After graduating from St. Croix, I found myself in need of a summer job. Thanks to a timely recommendation (I still owe that person a thank you!), I connected with Lisa LaFrance, who managed all of St. Croix’s technology infrastructure at the time. Lisa needed help updating the computer labs, installing software, and supporting teachers and staff, so I jumped in. I quickly discovered how much I enjoyed solving technical challenges.

For college, I chose UW-River Falls, following in my dad’s footsteps. My academic journey was anything but linear. I changed majors several times, moving from Communications to Digital Film and Television, before ultimately finding my place in Teaching English to Speakers of Other Languages (TESOL). While juggling classes, I drew on my St. Croix experience to work as a Desktop Support technician with the university’s Technology Services team.

After completing my coursework and student teaching, I realized that classroom teaching was not the right fit for me. Fortunately, a friend (a fellow campus tech services and theatre alum) reached out from a local software company that was hiring. I sent in my resume, landed the job, and have now spent the past ten years growing with the company. Today, I have the privilege of managing a talented team of cybersecurity software engineers. It challenges me daily but keeps me excited about the future.

What advice would you give to your high school self or to current students?

Be curious. Be adventurous. Don't let fear stop you from trying new things.

How did your experiences at St. Croix influence the kind of work you wanted to do in adulthood?

So much of what I do today is rooted in the opportunities and experiences I had at St. Croix. My current career is a direct extension of the hands-on work I started on campus during my summer before college.

Beyond my day job, I perform professionally around the Twin Cities with The Mystery Cafe and am a member of the St. Paul Saints Baseball Entertainment team. These experiences continue to bring me joy and fulfillment, and I credit St. Croix for providing opportunities to explore both my technical and creative sides.

Watch a video of Brittany as "Dawn Under" at the St. Paul Saints.