Dair Massey

Seattle-based senior product designer with a decade of experience building systems across streaming, commerce, story, and mapping surfaces. I design platform solutions used by 20+ brands at Outside to support exploration, engagement, and monetization, driven by the mission to get more people outdoors.

Outside
Design system powering 20+ brands.

Found
Luxury experiences built to scale.

IAC Streaming App
Cross-platform TV guide.

Cheat Sheet
Story surface viral by design.

About Me

I bring a hybrid background in UX, visual design, and product strategy, shaped by years of shipping digital experiences in both fast-paced startups and established media companies. My work blends data, research, and design systems to create products that are not just usable—but valuable and lasting.

From launching new subscription models to redesigning core user journeys, I’ve consistently driven growth and improved engagement across B2C and B2B platforms. I’ve also led and mentored design teams, built out scalable systems, and helped companies make smarter design decisions with clarity and purpose.

Over the years, I’ve led teams, scaled systems, and had the honor of receiving 5 web design awards while supporting platforms that served over 2.5 billion unique visitors. I’ve also spent 6+ years in design leadership roles, mentoring designers and evolving processes.

Lately, I’ve also been vibe-coding local tools and playful side projects that bring me joy—like a fully offline-compatible, Clippy-style assistant powered by LLaMA. It’s weird, nostalgic, and everything I love about tinkering.

Latest Personal Project

📎 Clippy Chat
Vintage AI Assistant built with PyQt6 + Ollama — Windows 98-inspired UI, runs locally or with network, no cloud required.

Connect on Linkedin | Resume | Reach out to reminisce about clippy

Home

Dair Massey

OutsideDesign system powering 20+ brands.

FoundLuxury experiences built to scale.

IAC Streaming App Cross-platform TV guide.

Cheat SheetStory surface viral by design.