Bryan Anaya

About

I've spent 27 years designing products that people actually use. Now I'm building my own.

Bryan Anaya

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 building:

  • Orchestrator — AI business advisor for SMBs. Formation, compliance, licensing, tax—one platform
  • PermitDashboard — LLC formation and permit finder with 6-step wizard and Stripe payments (live)
  • Val — Voice-first ambient scheduling for trades. Go backend, KMP mobile
  • Cherub Email — Multi-channel campaigns for small businesses with POS integration and AI content (live)
  • SwypMail — Y2K-themed casual email. Swipe interface, AI summaries, 54 TTS voices
  • UXC / Apex Attributions — Causal UX attribution platform
  • ClientFlow — Onboarding app for fintech. Streamlining client intake
  • Cherub Events — Event management with real-time comms, registration, attendee analytics

Background

I started in design before "UX" was even a job title. Over nearly three 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.

I write production code in TypeScript, Go, Python, and Rust. I self-host my own infrastructure on bare metal.


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 Orchestrator—an AI business advisor that connects formation, compliance, and licensing for SMBs. And Val—voice-first scheduling for trades workers who'd rather talk than tap. The through-line is making complex business operations simple for people who don't have time for complexity.

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

2021–Present

Independent Builder & Consultant

Founded Cherub Email. Building the Orchestrator ecosystem: AI business advisor, PermitDashboard, Val (voice scheduling), SwypMail, UXC/Apex. 8+ products, self-hosted infrastructure, selective consulting.

2022–2023

Head of UX, Anaconda

Built the company's first UX organization from scratch. Directed organizational transformation, advised C-suite on product vision. Cut design-to-development time by 60%.

2021–2022

Defense & Government, BrainGu

Led digital transformation for Air Force and Space Force. Earned commendation from the Chief of Staff. Pioneered secure, user-centered design in classified environments.

2017–2021

UX Strategy & Innovation, Indeed

Scaled design engineering from 5 to 80+ globally. Led platform architectural overhaul. Spearheaded WCAG compliance, training 300+ team members. Reduced software costs by $500K annually.

2016–2017

General Motors

Front-end engineering and building marketing sites across GM brands. Led a small team of junior developers to ship on tight timelines.

2007–2016

Microsoft & Enterprise UX

UX architecture for Outlook Web App. Directed design for Microsoft's web framework across 5,000+ properties. Pioneered hybrid designer-developer role.

1999–2007

Early Career & Freelance

First design job at Arroyo Seco Vineyards in '99. Then agency work, Flash development, interactive design. GE Security, Cingular/AT&T, Zebra Technologies. Ran my own studio. Taught at Art Institute of Portland. Built the foundation.

Let's talk.

Consulting, partnerships, or just to say hi.