Discovering Non-Traditional Pathways to Success

Killian Brackey

Co-founder and CTO at Sezzle


A Journey from Intern to CTO

I joined my team as a software engineering intern in college. It was my first professional career experience that I’ve had – outside of self-taught engineering work I had done prior. It was an interesting and probably non-traditional journey, going from intern to CTO/co-founder without a college degree.

Transitions of Life and Roles

The Early Years:

I’ve been a technologist for as long as I can remember. My first memories of tech revolve around figuring out how to use the hardware and software of my iPod. It was middle school when I first started getting into programming, learning code on a TI-84 calculator. I quickly fell in love, and it only progressed from there.

In high school, I started doing some web development and learned how to automate software. Once I entered college, I began focusing on economics but disliked the lack of hard science – so I changed tracks.

After I found my way back to computer science, I started working at the IT help desk – learning what tier 1 support looks like at a large corporation. I really valued that time and the knowledge that it provided me.

Joining a Company:

Shortly after my time at the IT desk, I met the CEO of a startup through an online tech group. The group was for engineers that were learning Python, and the CEO connected with me. I joined the company a few weeks later with my friend, who was also in the Python group.

The CEO was trying to build the team out in Minneapolis. At the time, there were only international developers, and the company was behind on the launch of its product. I developed a bond with him, as he was previously a developer, and he acted as a mentor to me. Our team looked into the code, trying to get an MVP to market.

Delving into the Product:

At that time, we were building a product that would give users cashback rewards for paying with their bank. The company was founded around a few data points that showed there was a huge drop in credit card applications between millennials and younger generations. We asked ourselves a major product question: why do users pull their credit cards out more than their debit cards? The answer was simple: users receive more benefits from using a credit card.

All of my lifelong tinkering and playing around with technology came together at this point. I had many tools in my possession and finally an outlet to use them on. In the early days of the company, we had just enough guidance to get a product to market; it was the kindling to start my fire. I definitely lived in that classic startup world, working 120 hour weeks but loving every minute of it.

We ended up coming in and changing a lot of the architecture of the product. Our team hosted a hackathon and rebuilt a lot of our core platform on another tech stack. These decisions we not always received super well by the team, but we built trust in our team by improving the product due to these changes.

Through the many iterations, I began to grow into the team lead position. I helped manage what our team was building and testing to find the right product-market fit. Our company eventually pivoted, as most startups do, and I moved from a team lead to the VP of engineering – due to my role in the platform.

Be notified about next articles from Killian Brackey

Killian Brackey

Co-founder and CTO at Sezzle

Mentorship ProgramsTechnical SkillsSoftware DevelopmentEmerging TechnologiesCareer ProgressionIndividual Contributor RolesLeadership RolesEngineering ManagerCTOTeam & Project Management

Connect and Learn with the Best Eng Leaders

We will send you a weekly newsletter with new mentors, circles, peer groups, content, webinars,bounties and free events.


HomeCircles1-on-1 MentorshipPeer GroupsBountiesBecome a mentorChangelog

© 2023 Plato. All rights reserved

LoginSign up