The short version.

Give me the problem nobody’s figured out yet.

I’ve spent more than 13 years designing complex software, the last seven at Microsoft. I prototype my way through most problems, and I’ve been a designer, a lead, and a manager along the way.

I’d rather build three versions than argue about one

When a problem is fuzzy, I start building. A rough prototype gives people something real to react to, and the conversation gets better fast. I usually make a few versions, so we’re comparing options instead of defending one. I’ll change my mind when the evidence says to. I’ll also push if I think something important is getting missed.

Usually outside

I’m a dad of three, and most of my free time goes to trail running, wakesurfing, skiing, golf, and the garden. I pick up new hobbies more often than I should, and the things I build end up on Making.

Tyler in a hallway, holding up a surfboard he built, its deck painted with blue contour lines.
A first-person view of a fishing rod held out over clear turquoise water toward a small island.
Tyler’s relay team in matching shirts under the finish arch of the 2026 Hood to Coast relay.

Building a surfboard, fishing, and finishing the 2026 Hood to Coast 200-mile relay.

Looking for my next role

I’m looking for a senior or principal product design role, ideally on AI, agents, or complex technical products. If that sounds like your team, email me.

tylerjwain@gmail.comResume⁠ (PDF, opens in a new tab)