Tyler WainHey, I’m Tyler.
I’m a product designer who likes getting dropped into messy problems: the product is still taking shape, the technology is changing underneath you, and people have different ideas about what should happen next. Somebody has to turn that into something real. That’s usually where I’m most useful.
I’ve been designing for more than 13 years, much of it on complex enterprise software. Most recently I spent seven years at Microsoft, working across automation, AI agents, supply chain, commerce, and customer experience. My last big focus was computer use in Copilot Studio, where I led design for AI agents that operate websites and desktop apps on a person’s behalf. Before that, I designed enterprise products and helped build design systems at Dell and Toptal.
How I work
When a problem is fuzzy, I’d rather build three versions of an idea than spend two weeks arguing about one in a document. Prototypes help me think, help teams disagree more productively, and give everyone something concrete to react to. I ask questions early, explore competing directions, and get more opinionated as the evidence gets better.
I work closely with engineering and product, bring other designers into the problem, and share unfinished thinking. I’m comfortable changing my mind, and comfortable pushing when something important is being missed.
I’ve moved between hands-on design, broader design leadership, and a stint as a design manager. I’m happiest in the middle: close enough to the work to prototype and sweat the details, far enough out to help a team make sense of the bigger system.
Outside of work
I’m a dad to three girls. I spend a probably unreasonable amount of time running trails, wakesurfing, skiing, golfing, and gardening, and convincing myself that some new hobby absolutely requires specialized equipment. The things I build end up on Making.
I’m at my best when there’s still something important to figure out.
What’s next
I’m looking for my next role: senior or principal product design, ideally on AI, agents, or complex technical products. If that sounds like your team, I’d like to hear from you.