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Building a design system — a case study

I landed my first User Experience role in 2018 at a mid-stage startup. With a customer base of over 8,000 paying users, the stakes were real. I had only a faint idea of what I had gotten into but I assumed there would be a script to follow, some direction provided, and a roadmap to complete. If expectations for my role were…nebulous, at least there would be a style guide that I could use, right?
Wrong.
As the first in-house UX designer I was on my own. No design files, no design team, not even a clear job description. I wanted to start building a UI kit right away but couldn’t effectively articulate why. Sure, it would make my job easier, but how would it benefit the business?
Fortunately, the company hired Brandon Beecroft, a well respected and highly experienced design manager a few months after I started. He too realized that without a symbol library to work with, our now two-person design team would be perpetually hobbled. With his support, I was given two weeks to create the beginnings of a design system.
WHERE TO START?
My first order of business was to collect all assets that might make my job easier, specifically Sketch files. Aside from a font file, there were none. Each and every design project started from scratch; new files, new artboards, new shapes…