Bryan Anaya

About

I've spent 25 years designing products that people actually use. Now I'm building my own.

The Short Version

I'm a UX leader turned product builder. I've led design at Fortune 500s and startups alike. My teams have shipped products used by millions. Now I'm channeling that experience into tools for designers and builders.

Currently shipping:

  • Cherub Email — AI-powered email marketing for small businesses with POS integration
  • Cherub Events — Event management with real-time communication and analytics
  • SwypMail — Email without the anxiety—swipe interface, AI summaries, voice playback
  • PermitDashboard — AI permit checklists and status monitoring for contractors
  • UX Connection — Causal attribution platform for design teams (coming soon)

Background

I started in design before "UX" was even a job title. Over two decades, I've worked across nearly every vertical: defense, fintech, job search, data science, construction, developer tools. Each one taught me something different about what users actually need versus what they say they want.

Previous stops include Microsoft, Indeed, and Anaconda, plus a handful of startups at various stages. I've built UX orgs from scratch, fixed broken ones, and helped companies finally understand why design matters to their bottom line.

The Philosophy

I believe designers who code ship better products. Not because everyone needs to be a full-stack developer, but because understanding what happens after the handoff makes you a better designer. I write production code, manage infrastructure, and occasionally dive into systems programming when a problem interests me.

My tech stack: TypeScript, Python, Rust, Go. React and Vue on the frontend. PostgreSQL, SQLite, Redis on the backend. Docker and Kubernetes for infrastructure. Local models and APIs for AI work.


The Long Version

I've never been good at just one thing. Design drew me in because it combined art with psychology with technology. But I've always been equally interested in the building part—the code, the systems, the infrastructure that makes design real.

That restlessness has been both a strength and a weakness. It's made me effective at shipping products because I understand the full stack. It's also made me terrible at staying in one place for too long. Every company eventually stops being interesting.

A co-worker told me once that I'd never truly be happy until I worked for myself. He was right. The moment came when I realized I was spending more energy navigating politics than solving problems. Corporate life optimizes for the wrong things.

What I'm Optimizing For Now

Impact over title. Products over presentations. Shipping over planning. I'm building tools that help people do better work. Some are for designers (UXC ecosystem). Some are for industries stuck in the past (construction tech). All of them scratch an itch I've had while watching how work actually gets done.

I'm bootstrapping everything. No VC, no hype, no pressure to grow at all costs. Just sustainable products that solve real problems.


Working With Me

I still do selective consulting for companies that need UX leadership. If you're trying to build a design organization from nothing, fix one that's not working, or figure out how AI fits into your product strategy—we should talk.

I'm also open to partnerships, collaborations, and interesting conversations. I respond to thoughtful messages.

Career Highlights

2024–Present

Independent Builder

Shipping Cherub Email, Cherub Events, SwypMail, and PermitDashboard. Consulting selectively.

2020–2024

Senior UX Roles

Led design at Anaconda, Indeed, and others. Built teams, shipped products, learned what doesn't work.

2015–2020

Enterprise UX Leadership

Microsoft and large-scale enterprise work. Learned how to navigate complexity and politics.

2008–2015

Defense & Government

Top-secret clearance. Designed systems where mistakes had real consequences.

2000–2008

Early Career

Agency work, startups, figuring out what UX even meant. Built the foundation.

Let's talk.

Consulting, partnerships, or just to say hi.