Cindy Schaller joined Upside in mid-2022. As she nears her third anniversary, we caught up with her to talk about her career and experience. 

Q: To get started, tell us about how you ended up at Upside.

Cindy: I joined Upside because several former co-workers who worked here had consistently great things to say about the culture. Their stories about the supportive environment, the incredible people, and the chance to make an impact convinced me it was a place where I could thrive – both professionally and personally.

Q: Here at Upside you’re a senior manager in engineering, but how did you originally get started in the software engineering field?

Cindy: I started in software engineering because I loved the challenge of breaking down complex problems and turning ideas into something real — with just a few lines of code. The creativity and logic behind building something from scratch felt like a perfect mix of puzzle-solving and innovation, and it pulled me in from the start.

Q: What advice would you give to other people starting out in software engineering?

Cindy: Stay curious, ask questions, and build relationships. Learn from everyone – teammates, mentors, even your own mistakes. Grow your technical and people skills in parallel and don’t stress about having a perfect plan. Your path will change, and that’s a good thing.

Q: What is an important lesson you’ve learned from your direct team?

Cindy: Support means different things to different people. Some teammates recharge with space and autonomy, while others thrive with frequent check-ins or a quick gut-check on direction. My teams have shown me how important it is to pay attention to those cues – what helps each person feel steady, motivated, and heard. It’s helped me approach leadership with more curiosity and adaptability. 

Q: What are your hobbies outside of work? 

Cindy: I’m part explorer, part homebody – I’m just as happy wandering local trails and lake paths with my dog as I am perfecting a flaky pot pie or obsessing over the perfect pizza crust. I also love diving into crafty projects – half the fun is seeing the possibilities, even if they remain as charming works-in-progress.

Q: If you could travel anywhere, where would it be?

Cindy: Somewhere to see the Northern Lights – probably northern Norway or Iceland. There’s something magical about the idea of being under a sky dancing with color, curled up in a glass-domed abode. I’ve caught a glimpse before, but getting to take it in fully with my own eyes feels like the ultimate unplug-and-reset experience.

Q: What superpower would you pick? 

Cindy: I’d choose rapid learning, like in The Matrix, where you just download a skill and instantly know it. I’ve got an endless list of things I want to learn, so the idea of picking up new abilities on the spot sounds amazing. Today: fluent in Italian. Tomorrow: gourmet chef. Next week: drumming pro. The possibilities are endless.

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