Sean Smith

Product design leader with 15+ years shipping AI-native, cross-platform products. Led design for Outlook Mobile and Mac through 2x+ MAU growth, managing a team of 11 including 3 principal designers. Now fractional with early-stage teams, using AI-assisted development to ship native and web products from concept to production. Player/coach approach: hands-on craft, systems thinking, leadership scope.

Sean Smith Design

Fractional Product Designer & Builder

Nov 2025 – Present
  • Product owner, designer, and builder at a stealth fintech, working hands-on with leadership on product direction.
  • Building Brukas solo (approaching launch, TestFlight access on request): product and business strategy, design, AI build, chat tuning and evals, and GTM.
  • Shipping AI workflow tools: Annotie for Mac and iOS, giving AI agents cleaner context through screenshots, video frames, and links; and Ghostties, an open source Ghostty terminal fork for tracking many agents running in parallel.
Microsoft

Microsoft Outlook

2021–December 2025 | Principal Product Design Leader
(previously Senior and Principal Product Design Manager roles)
  • Led design for Outlook Mobile and Mac, driving 2x+ MAU growth on Mobile and multi-X growth on Mac following the official launch of the new Outlook Mac app. Each semester the team planned 100-150 design work items across AI-powered experiences and core workflows.
  • Began exploring generative AI for Outlook in mid-2022 with GPT-3. Early prototyping informed how LLMs came into productivity workflows ahead of the broader Copilot push at Microsoft.
  • Player/coach leadership of a team of 11 across 6+ time zones (US, Australia, China, India, and at times London and Portugal). Included 3 principals (with a fourth on track) and 2 LEAP apprentices, both of whom were promoted from Designer 1 to Designer 2.
  • Led a rebuild of the Outlook mobile design system (years out of date), moving onto variants and variables, a foundation for AI-era design tooling.

Contact

Professional Development

Future London Academy
Executive Programme for Design Leaders ("Design MBA") | 2025-2026
Designer Fund
Design for Business Impact | 2019

Skills

Leadership & Strategy
Design Leadership, Team Management, Product Strategy, Storytelling, Mentorship, Human Centered Design, Cross-functional Collaboration
Favorite Tools Right Now
Claude Code, Cursor, Figma, v0, Vercel, Wispr Flow, Lovable, Jitter, Remotion

Education

Art Institute of California - San Francisco
Graphic Design | 2007-2010
Academy of Art
Graphic Design | 2006-2007