Dylan Kilgore

Summary

I design products at the intersection of AI, infrastructure, and developer experience. At Pulumi, I lead product design for a platform used by engineering teams building and managing cloud infrastructure at scale. My practice is AI-native — not just in the tools I use, but in how I approach design problems. I work directly with LLM-powered interfaces, agentic workflows, and AI-augmented design systems, and I bring a developer's sensibility to every surface I design. I write production code daily, which means I prototype in the real stack, speak fluently with engineers, and collapse the distance between concept and shipped product. Previously at Microsoft, I helped take the Immersive Reader from a concept to 46M monthly active users, originated the Microsoft Education assignments schema, and shipped Fresh Paint in-box on Windows. At Eightfold, I built the Octuple design system from zero to 10,000+ implementation points in eight months. I'm at my best on hard, ambiguous problems — the kind where design, engineering, and product strategy have to move together.

Experience

1. Pulumi · Senior UX Designer

   Jul 2024 — Present · Seattle, WA

   • Led UX for Pulumi Insights from public preview through general availability — cloud asset search, governance, policy-on-discovered-resources, and AI-assisted natural-language queries across AWS, Azure, GCP, and hundreds of other providers.
   • Design AI-native product experiences including LLM-powered infrastructure tooling and agentic developer workflows — across Pulumi Cloud, Facet (the design system), ESC onboarding and approvals, VCS integrations, Policy as Code, and Pulumi Neo (our agentic AI platform engineer).
   • Bridge design and engineering by contributing production code alongside design deliverables.
   • Build and evolve design systems for complex, technical user audiences.
   • Drive research strategy for platform engineers, DevOps/SRE, and application developer personas.

2. Eightfold · Lead UX Engineer

   Feb 2022 — Jul 2024 · Remote

   • Founded and led core development of Octuple, Eightfold's open-source design system, growing implementation from zero to 10,000+ production touchpoints in under eight months.
   • Pushed for Octuple to become Eightfold's canonical component library, making the case across product, engineering, and design leadership over teams' existing tooling and switching costs — the foundation underneath the 10,000+ touchpoint adoption that followed. The consolidation would not have happened without it.
   • Managed a cross-functional v-team of engineers using agile/scrum methodology, driving design system adoption across Eightfold's AI-powered talent intelligence platform.
   • Authored the UX migration strategy to consolidate local and third-party components into a unified design system, reducing fragmentation and improving velocity.
   • Established holistic regression testing methodology to ensure quality and risk mitigation across design system releases.
   • Winner, Eightfold Innovation Award 2022.

3. Microsoft · Design Engineer 2

   Mar 2017 — Feb 2022 · Redmond, WA

   • Designed the UX for AI-powered learning features built on Microsoft Cognitive Services — neural text-to-speech, neural machine translation, NLP for parts of speech and syllabification, speech-to-text — powering Immersive Reader, OneNote Live Captions, and Reading Assignments.
   • Supported Immersive Reader scaling from zero to 46M MAU across multiple platforms by creating a React prototype that scaled directly to production, and improving portability for use by any web experience.
   • Drove success within architecture of OneNote web application accessibility features, achieving SLA attainment of Level-C accessibility standards.
   • Led UX/UI prototyping for Reading Assignments and Immersive Reader, focusing on process, production, and engineering — contributing critical code to three winning (best overall, best in category) Microsoft Hackathon projects.
   • Drove process and creation of quick-cadence executive presentations representing Microsoft Education product vision.
   • Coordinated longitudinal research studies that culminated in extensible features originating from Microsoft Classroom into Microsoft Teams Assignments and OneNote class notebooks.

4. Microsoft · Design Developer 2

   Jun 2016 — Mar 2017 · Redmond, WA

   • Transitioned to leading engineering and front-end development for Microsoft Classroom and School Data Sync.
   • Managed on-call engineer rotation and live-site incident mitigation, including resolution tasks, telemetry implementation, and continuous-delivery-focused DevOps.
   • Innovated the Immersive Reader web application concept, taking the app from zero users to a fully formed reality.

5. Microsoft · Senior User Experience Designer

   Aug 2014 — Jun 2016 · Redmond, WA

   • Responsible for the creation of Microsoft Education products by creating the assignments schema in 2014.
   • Achieved transition of Microsoft Classroom and School Data Sync SaaS APIs to Microsoft Teams Assignments by creating innovative conceptual UX, design integration, and full-stack engineering.
   • Secured funding for Microsoft Education and successfully drove formal product group creation.
   • Created code for Fresh Paint's final release, an application still available on Windows 10 devices many years later.
   • Collaborated with design and engineering to implement Mix Gallery, enabling unlimited user sharing capabilities through front-end Office Mix code development.
   • Moved Microsoft apps to the cloud by authoring web applications, including the Immersive Reader.

6. Aquent · Design Integrator (Office Mix · Microsoft)

   Apr 2014 — Aug 2014 · Redmond, WA

   • Designed and developed interactive UX for the Office Mix application and website.
   • Contributed front-end code to Fresh Paint's Windows 10 update and Mix Gallery's sharing capabilities.

7. Aquent · Visual Designer · Creative Technologist (Amazon Advertising)

   Oct 2013 — Apr 2014 · Seattle, WA

   • Pioneered Amazon's first major HTML5-based ad takeover with the Cover Girl × Hunger Games: Catching Fire campaign — an early move off Flash at a moment when the digital ad industry was still SWF-heavy and the IAB HTML5 ad specs were freshly published.
   • Implemented innovative, IAB-compliant web-based ads as both visual designer and front-end developer, from conceptual design through production code.
   • Designed ad campaigns from concept to delivery for clients including Pepsi, Procter & Gamble, Johnson & Johnson, Clorox, Kimberly Clark, and Beiersdorf.

8. Aquent · Design Integrator · Prototyper (Microsoft Fresh Paint)

   Oct 2012 — Sep 2013 · Redmond, WA

   • Sole design developer of the Windows 8 Fresh Paint application UI, built end-to-end in XAML/C# with DirectX C++ integration for 3D paint effects.
   • Shipped in-box on Windows 8, reaching 1B MAU on the platform.
   • Invented the BoundsType property, enabling precise typographic grid control for designers and developers across the Windows platform.

9. Metia · Interactive Designer (Microsoft account)

   May 2011 — Oct 2012 · Kirkland, WA

   • Owned the Microsoft Dynamics creative platform, designing a multi-channel design system spanning video, web, and presentations — aligned to Windows brand standards.
   • Created the Microsoft Case Studies app for Windows Phone 7.5, providing a key channel for partner value demonstration.

10. Aquent · Media Author · Design Integrator (Microsoft)

    Feb 2008 — May 2011 · Redmond, WA

    • Defined the UI variable scope of Windows 8 by authoring types and interfaces in C++ to be interpreted by C# and XAML using Splash — supporting internal engineers and contributing to Windows Metro design success.
    • Created complex Now Playing and About feature UIs, implementing transition animations throughout the product using a new pattern (forward and backward hide/show).
    • Invented the BoundsType property, allowing developers to strip insets around blocks of type, giving designers high-quality grid control.

11. Beneficialmedia · Designer

    Jan 2008 — Present · Elko, NV

    Independent design practice — the through-line across product design, creative technology, and AI-integrated workflows. Current focus: AI-native design tooling, automated design pipelines, and interaction design consulting.

12. U.S. Marine Corps Recruiting · Combat Motion Photographer

    Aug 1998 — Aug 2006

    Visual storyteller and documentarian embedded with Marine Corps operations. Produced imagery and video across information operations, civil affairs, and recruiting — where I learned that the best design communicates clearly under pressure, for audiences who can't afford to misunderstand.