Jason Cypret
Twenty years and 30+ products shipped as a product and design executive. Today I work as an AI orchestrator: I lead the team, set the direction and write a lot of the code myself, so product, design and engineering run as one continuous loop instead of three handoffs.
Head of Product Experience
What I'm building now
I lead Product Experience at Worlds, covering design and front-end engineering for a platform where organizations direct, search and act on their physical AI in real time, with agentic workflows and reasoning AI across live camera networks.
In my first year, three codebases became one product on one design system, design moved in-house, the demo went live in any environment, and AI agents can now build dashboards on their own. Along the way the product helped win national retail, QSR, logistics and federal customers.
Codebases unified into one product
3 → 1
Dashboard widgets, all buildable by AI
~100
Design brought in-house
Agency → in-house
What else I've built
Grew UX from 1 to 30+ and launched 20+ products, from customer-facing apps to internal HR, learning and in-home sales platforms. Created Playbook, an open-source design system with 2M+ downloads across Ruby, React and SwiftUI.
Explore
“Built for speed, refined through iteration. That mindset still shapes how I work.”
Founder and creator. I designed, coded and shipped a CrossFit platform end to end: custom-trained AI coaching, native iOS and Android apps, and live chat. 70,000+ scores and 15,000+ workouts logged.
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“It started as one person's side project. Now it's part of how gyms train.”
Earlier chapters
Led design for a micro-credentialing platform now used by districts nationwide — from prototyping ideas to launching the full platform.
Explore
Investigative analytics for teams working through millions of documents — designing and iterating through four product evolutions.
Explore
From first sketch to launch-ready platform, I turn ambiguity into systems, and systems into momentum — on the team, and on the stage in front of a few thousand people.
My approach
I've spent twenty years on both sides of the handoff, leading design and engineering orgs and writing the code myself. AI collapsed that gap. Today I take ideas from concept to production directly, and I build the systems and team habits that let a small team use AI to move like a big one.
See all experienceWork experience
Leading design and front-end engineering for a physical-AI platform. Unified three codebases into one product, brought design in-house, hired the team and shipped AI-native features, from voice agents to dashboards that agents build over MCP.
Built and run a CrossFit platform for gyms across the U.S. and abroad, owning product, design, code and AI coaching end to end.
Grew the UX org from 1 to 30+, launched 20+ products including Power's first consumer app, and created Playbook, an open-source design system with 2M+ downloads.
Took a credentialing platform from R&D to market. It's now used by school districts and universities nationwide.
From the blog
Our CEO took the stage at Convergence AI Dallas and demoed the product my team has been building — agentic search, customizable dashboards, and real-time spatialization. This is what it felt like to watch that land, and why I think the companies that win the AI era will be the ones that make intelligence usable, trustworthy, and human.
I'm stepping into a new chapter at Worlds, taking on exciting (and slightly scary) challenges at the intersection of AI, design, and product leadership.
A candid look at the unglamorous side of solo entrepreneurship, from wrestling with AWS configurations to shipping incremental BoxBoard improvements, and the lessons learned about estimation, frustration management, and celebrating small wins.
