Christopher Kobar
Human experiences for an AI-fluent world
I design the boundary between what systems should do and what humans must decide
↪ Selected work
Oracle's First Agentic Expense Experience
Designing for a distracted traveler inside hard policy constraints — and shipping what three years of effort couldn't
How vision and technical reality can coexist when communication happens and goals align.
Unifying 5 Legacy Tools
Designing a hardcore diagnostic workbench for expert product support engineers.
Justice By Design
Redesigning federal sentencing calculation for 94 U.S. districts — built for the courtroom, where errors have human consequences.
Designing the AI That Replaces the Consultant
Led the initial UX vision for an EVP-sponsored NLP system built to make ERP implementation self-directing
How design can unify siloed product teams to drive high-value innovation.
↪ Vibe Coding Exploration
“Hey, Claude! Let’s make a Disney-like immersive mobile experience that brings the magic of a park visit to wherever you are.”
↪ My groove
⁂ Systems
Enterprise & complex platforms
Regulated tooling
AI-integrated experiences
⛰︎ Problems
Stalled products
Cross-functional misalignment
Vision-to-execution gaps
⛏︎ Method
Constraints → Framing
Framing → Alignment
Alignment → Shipped outcomes
✌︎ Culture
Design with engineers, not after
High autonomy and accountability
Clarity over consensus
↪ On my mind
↪ How I work
I started as a designer who coded my own front-ends in a browser before anyone thought to separate the two. On all the products I’ve designed, that instinct shaped my thinking. I still consider whether a layout breathes, a transition earns its milliseconds, and if the structure underneath can hold what the surface promises.
I care about craft—the tiny details, the aesthetic—as much as I care about systems. I've never understood why the industry treats those as different jobs. A component that looks right but behaves wrong is a failure. A system that works but feels like a chore is also a failure. I want both. And people deserve both.
I design close to the metal, drawing and coding in the room where engineering is making calls that will shape the experience whether design shows up or not. That’s not just a working style, but how I make sure the structure underneath can hold what the surface promises.
What I've learned from working in high-stakes, ambiguous territory like federal courtrooms, enterprise AI systems, and products with no design precedent, is that craft and judgment aren't separate skills. Knowing which details matter requires understanding what the system is trying to do, who it's doing it for, and what happens when it gets it wrong. That's my superpower.
↪ Who I am
Before design, I worked everywhere from restaurants to Congress to a zoo. I served in the Navy Nuclear Power program. I've spent decades devising RPG systems, rules, worlds, and consequences. I published ten books. I dabble in weird fiction, podcasting. Sometimes I still pick up my guitar.
I've picked up some stories. I've been detained by the Syrian and Lebanese military. Had an awkward encounter with a U.S. president. Wiped out on a motorcycle at 95 mph. Busked in the NYC subway. Danced flamenco. Played a Secret Service agent in a Spielberg film. Saw a UFO. And got my piece of the Berlin Wall the old fashioned way. All true. Buy me a cider sometime.
I have a teen daughter, a Utah wife, and two cats who have never once been impressed. I studied philosophy at UConn — Phi Beta Kappa — and learned a few things at NYU, the University of Mannheim, and the Connecticut School of Broadcasting. I've lived in ten states, but I'm back in Connecticut, a stone's throw from the submarine base where my tale began.