Hey there

My name is Darin Cassler. I’m a systems thinker, product strategist, and occasional open source troublemaker with two decades of experience building for the web, enterprise, and everything in between. Over the years, I’ve served as engineer, designer, architect, advisor, and executive partner—sometimes all at once. I’ve worked across startups, agencies, and global firms, adapting to the shape of the problem and the velocity of the team.

I occasionally advise founders and teams navigating the fog—figuring out what to build, how to position it, and how to make sure it still feels human.

Right now, I’m building a multi-brand product suite in stealth, with a few open source projects on the side to help test ideas in public. My writing lives alongside that work—it’s a kind of running commentary on the questions I’m living through: what it means to design for intent instead of interaction, how AI changes the grammar of software, and how we might build systems that feel more human without pretending to be.