About – Chance Chipman

About Me

I’ve been building for the web since I was 16, starting with self-taught HTML, CSS, and Flash, making sites before I knew what the job was actually called.

That early start eventually led to 12+ years of professional product design. Along the way, I realized I wasn’t interested in just making things look good. I wanted to understand why something should exist, whether it was working, and how to make it better.

Today I’m a Senior Product Designer at Pillar4 Media, where I drive UX strategy and experimentation across 10+ consumer and partner brands. That work has generated $25M+ in measurable revenue over three years. Before Pillar4, I spent five years at BowFlex, where I co-founded the company’s first Web UX team and led design across six brands including BowFlex, JRNY, and Schwinn Fitness.

Most of my experience lives in media, affiliate commerce, and DTC ecommerce, but the problems I solve (conversion architecture, experimentation systems, cross-functional alignment, product discovery) translate directly to SaaS, ecommerce, and any product environment where design has to earn its impact through measurable outcomes.

How I Think About the Work

AI is part of how I design now, not a separate initiative and not a buzzword. I currently use Claude and Claude Code across the full design lifecycle: research, writing, UX flows, design generation, prototype code, design tokens, the whole stack. The gain isn’t just speed. It’s that I can push harder on the work that actually matters (strategy, structure, performance) because the mechanical parts move faster. I’ve also been pushing AI adoption into product and engineering, because the biggest gains show up when the whole team moves at the new pace, not just design.

This is the thing I push hardest on with my team and with myself. Changing a color? Why. Moving a CTA? Why. If you walk into any design review knowing your reasoning, you’ll almost never get pushback, and you’ll make better decisions because you actually understand what you’re doing. Design without a reason is decoration.

It’s tempting to jump into visual design, especially when stakeholders want to see something tangible. But I always start with the experience before the interface. Get the structure, flow, and hierarchy right first, and the visual layer has something solid to build on. Skip that step and you end up polishing something that doesn’t actually work.

This one surprises people, but I think of engineers as our primary clients. They work directly off our output. If we make their job easier with clean handoffs, clear specs, and structured communication, the whole organization moves faster. I’ve seen that translate directly into shorter iteration cycles and better results.

I like sitting inside mouse tracking tools and watching how users actually interact with pages. Not just a single component, but how everything works together as a whole. I work closely with analysts on the quantitative side and I’m involved at every step, not just waiting for results. Over 45+ structured A/B tests, I’ve probably learned more from the ones that lost than the ones that won.

How I Work With Others

I got my first real taste of leadership at BowFlex. After co-founding the Web UX team, my mentor left the company and I became the sole UX designer across the entire web experience. That’s where I learned to own the strategy, not just the screens.

At Pillar4, I came on alongside a team of 4 UX/UI designers and 2 visual designers under a design director. After layoffs, the team shrank and I picked up more strategic ownership. We’re now at 3 designers and I own the design strategy, partnering closely with product managers across every brand.

The most important thing I’ve learned about working with other designers is that there’s no one approach that works for everyone. People learn differently, work differently, and need different things from their teammates. I try to figure out strengths and work within them rather than forcing a single process.

I’m also probably more transparent than most people are comfortable being. I don’t love the corporate game, and I’ve found that being direct and honest builds more trust than managing perceptions ever could.

I’m based in Central Oregon with my wife, surrounded by high desert landscape that surprises most people who hear ‘Oregon.’ Outside of work, food is a big part of our lives. We’re always trying new restaurants, experimenting with recipes at home, and mixing cocktails every weekend (a hobby I’ve taken more seriously than I probably should). I’ve been riding motorcycles since I was 7, I love spending time outdoors, and I’m almost always in the middle of some kind of home or backyard project. I like to think of myself as an outdoorsy homebody, which somehow makes perfect sense here.