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Advice / Career Paths / Career Stories

How This Principal Software Engineer Learned to Handle Challenges and Grow as a Leader

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Willie Miller, a principal software engineer at Upside.
| Courtesy of Upside

At an early age, Willie Miller was fascinated by computers, software, and programming. When he learned you could study technology in college and earn a degree, he jumped at the chance to immerse himself in that world. After gaining valuable experience at a startup, Miller decided to pursue a promising opportunity at Upside.

“Working at a startup provides a rich experience for someone to learn a lot and make an impact on the trajectory of a company,” he says.

In 2019, he entered the retail technology company as a senior software engineer; today, he’s a principal software engineer.

Upside’s supportive culture has empowered Miller to refine his skills and further develop his talents. He’s also contributed to the company’s mission of transforming brick-and-mortar commerce.

Here, Miller shares what he’s responsible for in his role, how Upside has actively encouraged his professional growth, and why he appreciates the company’s values.

What attracted you to Upside, and how did you know the company would be a good fit?

I knew I wanted to work at another startup. When I had my first discussions with Upside, I knew this startup was different. I was sold on their core business model and the focus on doing good for brick-and-mortar businesses and their customers.

What are your core responsibilities as a principal software engineer? Why does this work excite or inspire you?

As a principal software engineer, I work with our product team’s ideas to shape and design the path from an idea to reality. I work with my teammates to deliver those results. I like building and making things, so being able to build software on a regular basis keeps me excited.

You’ve been at Upside for nearly six years. How has the company encouraged and supported your professional development and growth? In what ways does Upside nurture and cultivate tech talent?

With my relatively long tenure at Upside, it’s clear that the company cares about progressional growth. Upside provides opportunities to learn and grow—whether through projects that stretch your abilities or gaining a new skill through training.

What are some unique challenges to your work at Upside, and how have you overcome them?

Upside has grown a lot since I joined, and it continues to maintain a startup mindset. Upholding that mindset means a sense of ownership and flexibility for individuals. That ownership can be challenging as priorities can change quickly. For me, staying tapped into the priorities of the business helps me understand why sudden changes are sometimes required.

What’s one project or accomplishment you’re most proud of, and why? How did your team and Upside’s work culture assist in this success?

One of my proudest accomplishments was a project that didn’t get launched. It was a long-running effort that had a lot of twists and turns. Although it didn’t get released for reasons outside of the project, I learned a lot. I worked with many people across the company and got an in-depth look into the full life cycle of a very large project. Upside was supportive during the process, helping move the project forward.

How have you changed or evolved as a leader since first joining Upside? What valuable lessons have you learned?

I’ve learned a lot about how a business is run. Upside does a really good job of explaining how the business works, both in process and financially. This has taught me how to tie the work I do to business goals.

Why do Upside’s values and mission resonate with you? How does your work incorporate or reflect the values of “Be an Owner” and “Represent the Real World”?

Upside’s mission brought me to the company in the first place. The work I do has an impact on the real world and real people. The ability to own projects and do my part to further this mission is what I’m at this company to do.

What advice would you give to those pursuing a leadership role at Upside? What skills should a potential candidate acquire to thrive at the company and in their tech careers?

Be clear and direct with communication—that’s kind of advice for life in general. However, communication is of the utmost importance at Upside.

Outside of work, what are you most passionate about, and why?

I’m an avid baker, both sweet and savory. I enjoy the process of baking complex desserts and eating the results.