19 Years From Designer to Executive: What Product and UX Taught Me

I started out designing screens for small software products. Nineteen years later I lead product and UX for a mobile platform used by more than 500,000 truck drivers. Somewhere in between, the job changed, the tools changed and I changed. People sometimes ask what that path looked like. It wasn't a straight line, and most of what I know I learned by getting it wrong first.

So this is my honest list. The good, the bad, what I wish someone had told me sooner, and the part that made all of it worth it.

Where It Started

For my first nine years I was the chief designer at a small software company. Small means you do everything. I designed point-of-sale and financial software, sat next to the developers building it, helped test it and was there when it launched. When the App Store was brand new, we took an iOS music app called Quik Tracks from an idea to the store. There was no mobile playbook yet, so we wrote our own as we went.

That stretch taught me something I still lean on. You understand a product far better when you're responsible for all of it, not just the screens.

After that came contract work prototyping audit software for two of the largest accounting firms in the world, then a few years leading marketing and design at a creative agency, where the work ranged from a 3D patient-education app for a spine surgery practice to an event platform built from scratch. Then, in 2018, I joined Transflo as a senior UX and product designer. I've grown with the company ever since, first building a full Product Experience department that brought creative, video, UX, research, product marketing and knowledge base writers and subject matter experts together under one roof, and now as Head of Mobile Product and Product Design.

The Good

The best moments in this field are small and quiet. A driver finishes a task in a few taps that used to take a few minutes, and doesn't think twice about it. When we cut our document workflow from ten steps to three, nobody threw a party in the truck cab. They just got paid faster. That's the job working.

The other good surprise was learning that UX can speak the same language as the CFO. The first self-service knowledge base I launched saved roughly $1.2 million a year. A later rebuild, with AI-assisted self-service, saved about $1.3 million and let 95% of users solve problems without waiting on an agent. Those numbers changed how leadership saw our team. We stopped being the people who make things look nice and started being the people who make the business run better.

And I've loved the variety. Audit software, medical animation, event planning, trucking, a home services business. The users are completely different. The core questions never are. Who is this for, what are they trying to get done, and what's in their way?

The Bad

For a long time, design got invited in at the end. The requirements were set, the timeline was set, and we were asked to make it pretty. That's a hard place to do good work from, and it took me years to learn how to earn an earlier seat.

Process was another fight. When I arrived at Transflo there was no formal Agile practice. I became the company's first Certified ScrumMaster and helped set up the routines we needed. Some people saw it as overhead at first. What I learned is that good process isn't bureaucracy. It's what gives a team room to focus.

Then there was the move into management, which nobody really prepares you for. You design less. You sit in more meetings. You have conversations you'd rather avoid, and your wins start to look like other people's wins. For a while I missed the craft so much it hurt. It took time to see that building a team is its own kind of design work.

I've also shipped things that looked great in review and barely got used. When I trace those back, almost every one of them skipped real time with customers. That lesson stuck.

What I Wish I'd Known Sooner

Learn the business early. Revenue, cost, churn, support volume. I spent years talking about usability when I should have been talking about outcomes. The day I started connecting design work to numbers leadership already cared about, doors opened.

A prototype beats a slide deck. Early at Transflo, our team put together five validated prototypes in a single week. That did more to align executives than any presentation I've ever given. People argue with documents. They react to things they can touch.

Systems are how you scale yourself. Moving our team to Figma and growing a design system to about 200 reusable components across four products did more for speed and consistency than any single project. It's not glamorous work. It pays off every day after.

Hire for curiosity, then get out of the way. I've hired ten people onto my teams over the years and promoted designers into senior and lead roles, and the ones who thrive are the ones who ask why before they ask what. Keeping around 80% of that team, with real career paths and leveling, has mattered more to our results than any tool we bought.

You don't need permission to lead. Nobody asked me to start a Voice of the Customer program or an NPS program. They just needed to exist, and once they did, they shaped our priorities for years.

The Most Rewarding Part

It's the people. Not the app ratings, although getting our driver app to 4.8 on iOS felt great. It's watching a designer I hired present work to executives with total confidence. It's an engineer telling me a prototype saved them a week. It's sales, engineering and customer success sitting in the same room and agreeing on what the customer actually needs.

Somewhere along the way my job stopped being about making the best screen and started being about building the team that makes them. I didn't expect to love that as much as I do.

If You're Just Starting Out

Stay close to the people who use what you build. Learn how your company makes money. Build things people can click, not just things they can read. Find a few leaders who will tell you the truth, and later, be that person for someone else.

Nineteen years in, I still get the same small thrill when something just works for someone. That part never wore off. I hope it doesn't for you either.