Sean Smith
Product Design Leader. Player-coach who leads human teams and AI agents.
Professional Summary
Sean Smith is a product design leader and builder with 15 years across cross-platform productivity, B2B, and consumer products. He led product design at Microsoft Outlook from 2021 to 2025: a global team of 11 designers, cross-platform coverage across iOS, Android, and Mac, and monthly active usage that more than doubled at hundreds-of-millions scale. Before that, he was the founding in-house designer at MileIQ, where he shaped ML-driven product experiences before "AI" was a hiring requirement. The product was acquired by Microsoft.
His thesis: the player-coach model applies to people and to agents. He runs an AI-native workflow using Claude Code daily, has authored 15 or more skills for it, and built Ghostties, an open-source terminal fork optimized for running parallel AI agents simultaneously. Brukas, his solo-built AI focus coach in native Swift, is live on TestFlight. He leads both: managing human design teams at scale and building production software independently.
Currently
Currently (June 2026): open to a full-time design leadership role at a B2B, productivity, or AI-native company (Series A to pre-IPO) where craft and product thinking both matter. Available for fractional and advisory conversations in parallel. Side projects continue regardless. Reach him at sean@seansmithdesign.com.
Career History
AI Product Designer, Builder, Leader
Independent · Nov 2025 to Present
Designing and building AI-native products independently. Solo-built Brukas (native Swift AI focus coach, live on TestFlight). Authored a suite of 15 or more Claude Code skills for product and design workflows. Built Ghostties, an open-source terminal fork for parallel Claude Code agents. Open to fractional and advisory work.
Principal Product Design Leader, Microsoft Outlook
Microsoft · 2021 to 2025
Led cross-platform product design across Outlook Mobile (iOS, Android) and Outlook Mac simultaneously. Monthly active usage more than doubled during his tenure at hundreds-of-millions scale. Managed a global design team of 11. Led design for Outlook Copilot: AI-powered email features across mobile and desktop. Designed the Dynamic Action Bar, Microsoft's most visible AI surface for email at launch. Owned the cross-platform design system across iOS, Android, and Mac.
Senior Designer and Senior Design Manager, Microsoft MileIQ and SMB Incubation
Microsoft · 2015 to 2021
Guided MileIQ's design through Microsoft acquisition and integration. Led design for SMB incubation efforts. Spanned both IC and management roles across the period. Products included MileIQ, Spend, Visits, and Money in Excel.
Lead Product Designer, MileIQ (Mobile Data Labs)
MileIQ · 2015
Founding in-house designer at MileIQ. Partnered with founders to refine the core mileage tracking experience. Shaped ML-driven product experiences before the AI category had a name. Product vision contributed to Microsoft acquisition.
Lead Product Designer, Best Apps Market and Fetch
2012 to 2015
Led product design and design engineering across consumer apps. Mobile product design and frontend implementation, including Material Design. Preceded by freelance design work from 2009 to 2012.
Areas of Expertise
Sean's expertise spans 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, and UX strategy.
- Product Design Leadership
- AI-Native Product Design
- Agentic Workflow Design
- Cross-Platform Mobile and Desktop Design
- 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
Featured Projects
Outlook Dynamic Action Bar
Microsoft · iOS, Android · Shipped
Signature design pattern for Outlook Mobile and Microsoft's most visible AI surface for email at launch. Led design from conception through cross-platform implementation at hundreds-of-millions-user scale.
MileIQ
Founding Designer · iOS, Android · Acquired by Microsoft
Founding in-house designer at MileIQ. Shaped ML-driven product experiences before 'AI' was a standard product requirement. Product vision contributed to the Microsoft acquisition.
Brukas
Solo-built · macOS native Swift · Live on TestFlight
AI focus coach built from concept to live product by Sean alone. Native Swift, OpenRouter for multi-model experimentation, Supabase backend, proprietary design system. Demonstrates solo product ownership from zero to shipped.
Ghostties
Open source · macOS terminal · Available on GitHub
Open-source Ghostty terminal fork optimized for running parallel Claude Code agents simultaneously. Built to support an AI-native design and engineering workflow. Reflects how Sean operates daily.
Claude Code Skills Suite
Authored · Claude Code CLI · In daily use
A suite of 15 or more authored skills for product design workflows, orchestrator scaffolding, design quality review, and session lifecycle management. Infrastructure Sean built for his own practice, now a core part of how he works.
Frequently Asked Questions
Who is Sean Smith?
Sean Smith is a product design leader and builder based in Petaluma, CA. He led product design at Microsoft Outlook from 2021 to 2025, managing a global team of 11 and designing cross-platform experiences used by hundreds of millions of people. He was the founding in-house designer at MileIQ, where ML-driven product design contributed to the company's acquisition by Microsoft. He now builds AI-native products independently, runs an AI-native workflow using Claude Code daily, and is open to a full-time design leadership role.
What does Sean Smith build with AI?
Sean builds production software using AI as a primary collaborator. He has authored 15 or more Claude Code skills used daily in his practice, including an orchestrator scaffolding pattern and a design quality review system. He built Ghostties, an open-source Ghostty terminal fork tuned for running parallel Claude Code agents. His current solo product, Brukas, is a native Swift AI focus coach live on TestFlight, built from concept to production by Sean alone.
What is Sean Smith's leadership style?
Sean operates as a player-coach: he has managed design teams of 11 at Microsoft and pushed pixels on the same products. His view is that most product dysfunction is an upstream definition problem, not a craft problem. A design principle should be specific enough to decide something; if it does not eliminate options, it is not doing work. He applies the same framework to human teams and to AI agents: set the direction, delegate the execution, stay close to the craft.
Where has Sean Smith worked?
Microsoft Outlook, Principal Product Design Leader, 2021 to 2025. Microsoft MileIQ and SMB Incubation, Senior Designer and Senior Design Manager, 2015 to 2021. MileIQ (Mobile Data Labs), Lead Product Designer and founding in-house designer, 2015. Best Apps Market and Fetch, Lead Product Designer, 2012 to 2015. Freelance Design, 2009 to 2012. Currently designing and building independently since November 2025.
How do I reach Sean Smith?
Email sean@seansmithdesign.com. LinkedIn: linkedin.com/in/seansmithdesign. GitHub: github.com/SeanSmithDesign. X: x.com/seansmithbuilds. Website: seansmithdesign.com.
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