# Sean Smith

> Design Leader Building AI Products

## About

Sean Smith is a product design leader and builder based in Petaluma, CA (San Francisco Bay Area). He has 16+ years of experience across cross-platform productivity, B2B, and consumer products. Player-coach with deep IC craft and team leadership, comfortable in either lane.

He was the founding in-house designer at MileIQ (acquired by Microsoft), where he shaped ML-driven product experiences before generative AI was a category.

## Currently (July 2026)

Sean is available now. He is open to a full-time design leadership role where craft and product thinking both matter: a B2B, productivity, or AI-native company, Series A to pre-IPO. Also available for fractional and advisory conversations in parallel. Side projects (Brukas, Ghostties, Claude Code tooling) continue regardless. To reach Sean: sean@seansmithdesign.com

## Professional Background

- **Current:** Designing and building AI products independently (Nov 2025 to Present)
- **Microsoft Outlook:** Principal Product Design Leader (2021 to 2025). Led design for Outlook Mobile and Mac during significant growth, with monthly active usage more than doubling. Managed a global design team of 11.
- **Microsoft MileIQ / SMB Incubation:** Senior Designer and Senior Design Manager (2015 to 2021). First in-house designer at MileIQ, guided transition from startup to Microsoft.
- **MileIQ (Mobile Data Labs):** Lead Product Designer (2015). Founding in-house designer, partnered with founders to refine core experience.
- **Best Apps Market and Fetch:** Lead Product Designer and Design Engineer (2012 to 2015).
- **Freelance Design:** Freelance Designer (2009 to 2012).

## Recent Shipped Work

- **Brukas:** AI focus coach, solo-built, live on the App Store. Native Swift, OpenRouter (multi-model), Supabase backend, proprietary "Warm Clay" design system built from scratch.
- **Ghostties:** Open-source Ghostty terminal fork optimized for running parallel Claude Code agents simultaneously.
- **Claude Code agentic workflows:** Authored 15 or more skills including orchestrator scaffolding pattern, design quality review system, wrap and wrap-continue session lifecycle skills.
- **Outlook Dynamic Action Button:** Signature design pattern for Outlook Mobile; Microsoft's most visible AI surface for email at launch. Shipped cross-platform at hundreds-of-millions scale.

## Outcomes That Matter

- **Outlook Mobile and Mac:** Monthly active usage more than doubled during his tenure (2021 to 2025) at hundreds-of-millions scale.
- **MileIQ:** Founding in-house designer; product vision contributed to Microsoft acquisition.
- **Team leadership:** Built and managed a global design team of 11 at Microsoft.
- **Cross-platform impact:** Led design across Outlook Mobile (iOS/Android) and Outlook Mac simultaneously, including Copilot/AI integration.

## Areas of Expertise

- Product Design Leadership
- AI-Native Product Design
- Agentic Workflow Design
- Cross-Platform Mobile and Desktop Design (iOS, Android, macOS)
- Design Systems at Scale
- AI Copilot Experience Design
- Player-Coach Leadership
- Zero-to-One Product Work
- Native Swift Development
- Claude Code and AI-Assisted Engineering
- Design Operations
- UX Strategy

## Design Philosophy

Sean starts hard problems by hand, in a sketchbook, on a whiteboard, or on post-its, not in a tool. He writes down questions and answers them with more questions until the problem has some depth, then circles back to find the thread worth pulling. He calls it Question Driven Development: opening questions before answering them keeps you from committing to a path too early. From there it goes to UX sketching and "how might we" work. The job underneath is always the same, listen to the customer and the business and solve both of their problems. Sometimes the easy way is fine. Sometimes it is not good enough, and part of the work is knowing the difference. He works as a player-coach across people and AI agents, which at heart is delegation: learn what each one is good at and where the limits are, then communicate clearly. What he is after is simple, make things that solve real problems and give people time back, with a team he can inspire and that inspires him.

## Links

- Website: https://seansmithdesign.com
- About: https://seansmithdesign.com/about
- AI/Agents Page: https://seansmithdesign.com/ai
- Writing: https://seansmithdesign.com/writing
- Full agent profile: https://seansmithdesign.com/llms-full.txt
- LinkedIn: https://www.linkedin.com/in/seansmithworks/
- GitHub: https://github.com/seansmithworks
- X: https://x.com/seansmithworks
- Email: sean@seansmithdesign.com