
I’m Jason Cowsill. I design and build software. I write and play music. I make things on and off the web that probably don’t need to exist but are better for existing.
I live in Tehachapi, California with my wife Jackie, where we split our time between screens and stages.
The work
I lead product design at Singlemind, an agency in Oregon where we take complex ideas from early concept through shipped software. I’ve been doing some version of this for close to thirty years.
I love the moment before the thing exists. The ambiguity of an unshaped problem. The slow process of pulling something coherent out of noise, then refining it until it feels inevitable. That’s the part I keep coming back for.
When I can, I design in code. Working software, not pictures of software. What a client reviews should be the real thing, not a static mockup waiting to be reinterpreted by someone else. The gap between a design and its implementation is where most products lose the plot. I’d rather skip it entirely.

Before Singlemind, I spent fourteen years at Concentric Sky, eventually as VP of Product. Across both, I’ve designed and shipped over three hundred projects, including work for The World Bank, National Geographic, NASA, and Encyclopedia Britannica. Those taught me that the hard part is rarely the technology. It’s deciding what should exist in the first place.
I’m paying close attention to how AI changes this work. Not just the obvious acceleration, but the deeper shift in what “building software” even means when generation is cheap and judgment is expensive.
This site is partly an attempt to think through that question by making things rather than just theorizing about them.
The music
My dad is Bob Cowsill of The Cowsills. I picked up the guitar as a teenager and never really put it down.
Jackie and I have been writing and performing together since 2007. We play across the Pacific Northwest. Folk, rock, outlaw country, pop, plus covers that span the 1940s to today. We both sing. We both write the songs. I play guitar and try to keep up.

You can hear some of our music in the Sounds section, or find us at jackieandjason.com.
Get in touch
I’m always up for a conversation about design, tech, music, or whatever you’re building.