Gary J. Anderson
Principal Design Director, MonetizationMicrosoft AI Experiences
Summary
I’ve been a designer, researcher, product manager, and design manager/director. Over 20+ years in creative roles at Microsoft, Costco and SUPERVALU. My work has centered on how products earn their keep: monetization and advertising, shopping and commerce, payments, growth, and loyalty; spanning consumer and enterprise usage. 8+ years teaching UX at the University of Washington and Bellevue College.
Experience
Principal Design Director
- Lead design for advertising and commerce across Copilot, Bing and MSN. At peak, an org of 3 managers and 27 designers; today 1 manager and 10 designers, 8 of them senior or principal.
- Turned the org AI-native: every designer builds in code and manages AI agents as part of how they work.
- My teams’ work helped move ads from a top-3 driver of negative Edge feedback to a long-tail issue.
- Hired 8 principal and senior designers in 2025, with rewritten role descriptions, a whiteboarding exercise and interviewer training.
- Co-wrote monetization principles for Copilot and cross-product principles for organic and sponsored commerce (e.g. shopping).
Principal Design Manager
Team: 1 manager + 18 designers and contractors
- Reframed Microsoft Rewards from incentives to loyalty: led loyalty research across Brazil, India and the US, and shipped streak protection and micro-donations to nonprofits.
- Built a crowdsourced design-template pipeline that generated more than 10,000 native ad templates.
- Secured funding for and directed Microsoft Clarity’s rebrand, and co-wrote its brand guide.
- Introduced shared PM/design backlogs and weekly scrums across five workstreams.
Senior Design Manager
Team: 11 designers
- Managed a studio of 11 designers: set the operating rhythm, career-progression reviews and onboarding.
- Used resource-allocation data to secure engineering funding for two additional designers.
Senior Design Researcher
- Led the pubCenter redesign (navigation, data grids, core forms) and moved it to Microsoft’s Fluent design standards.
- Co-defined an inclusive-research standard and led the team’s accessibility plan and training.
UX Program Manager
- Created the user-centered design process for a Microsoft Services organization.
- Ran 14 research and design sprints delivering 30+ validated features, including field research in India.
- Managed up to eight vendor resources and cut their cost by 40%.
UX Engineer (UX Lead)
- Led and mentored a team of 13 full-time UX designers.
- Set the strategy for, and oversaw, all user research and design work.
- Represented and evangelized research and design at every level of the organization, up to the EVP and CIO.
Education Developer → UX Leader
UX Leader (UX Manager)2012
- Managed a team of three full-time UX designers.
- Developed and rolled out UX training and processes for IT Business Delivery.
- Stayed hands-on in UX research and design alongside the team.
Senior User Experience Analyst2008–2012
- Planned and ran user research, designing and prototyping to support it.
- Created and taught usability and data-visualization training courses.
Education Developer / Manager2005–2008
- Designed training materials for 20+ corporate initiatives and projects.
- Managed four full-time instructional designers.
- Facilitated multi-day leadership training for corporate and retail associates.
Growing designers
- Built a shared view of designer levels and readiness, so promotion conversations start from evidence.
- Created onboarding that gets new hires productive fast: values, tools, product map and partners.
- Mentor 10–15 people a year, inside and outside Microsoft, especially people from non-traditional backgrounds.
Teaching & community
- Instructor, Applied UX Design, University of Washington Continuum College 2020–2025
- Instructor & UX Advisory Board, Bellevue College (designed its first Interaction Design course) 2015–2019
- Guest lecturer, research in product management, Stanford Continuing Studies 2018
- Founding member, Alumni Leadership Board, UW Human Centered Design & Engineering 2019–2020
Education
- MS, Human Centered Design & Engineering, University of Washington 2016 (Award for Academic Excellence)
- Master of Business Administration, Boise State University 2005
- BS, Psychology (Business minor), Montana State University 1998
Certifications
- Certified Usability Analyst (CUA), Human Factors International 2010
- Scaled Agile Framework (SAFe), Scaled Agile 2016
- Accessibility in Action, Microsoft 2020
Skills
- Leadership
- Org design & scaling · Hiring & interviewer training · Coaching & mentoring · Executive storytelling · Design operations
- Research
- Usability testing · Contextual inquiry · Perception & quality studies · Card sorting & IA · Inclusive research
- Design
- Interaction design · Information architecture · Design systems · Accessibility (WCAG) · Data visualization
- AI
- Prototyping in code with AI · Agentic & generative UI · LLM evaluation design · AI adoption in teams
Recognition
- Diverse & Inclusive Award, Microsoft Shared Engineering Services 2019
- Award for Academic Excellence, UW Human Centered Design & Engineering 2016