Dylan Kilgore

Summary

Product designer with deep engineering experience, at the intersection of AI, infrastructure, and developer experience. Leads product design at Pulumi, including governance and policy remediation in Pulumi Neo, the agentic AI platform engineer. Founded the Octuple design system at Eightfold (zero to 10,000+ implementation points in eight months), and helped take Microsoft's Immersive Reader from concept to 46M monthly active users. AI-native practice; writes production code across the stack.

Experience

1. Pulumi · Senior UX Designer

   Jul 2024 – Present · Remote

   • Took Pulumi Insights (now Governance) through GA: weekly active teams tripled in its first full quarter, and the Policy Findings launch week set an all-time high for teams actively using policies.
   • Redesigned OIDC onboarding for Pulumi ESC: four manual console steps became one guided flow, and the share of teams creating environments with a cloud login provider roughly doubled.
   • Lead Pulumi's design practice: started the weekly UX critique and design team meeting in 2024 (both still running), mentor engineers daily on product and UX design, and drafted the vision document for Pulumi Governance.
   • Built Connect cloud accounts on the same onboarding pattern: setup went from hours or days to about three minutes for a batch of accounts, and accounts connected in a team's first setup more than doubled.
   • Design AI-native product experiences including LLM-powered infrastructure tooling and agentic developer workflows across Pulumi Cloud, the Pulumi Design System, ESC onboarding and approvals, VCS integrations, Policy as Code, and governance and policy remediation in Pulumi Neo (our agentic AI platform engineer).
   • Built a custom design sandbox in Storybook on the Pulumi Design System's Web Components that emulates production, plus an agent harness that fields Linear request tickets and generates first-revision prototypes autonomously, which I then vet with my own judgment. I create new experiences in it every day.
   • Designed growth surfaces end to end: refreshed Billing & Usage to map to Pulumi's latest pricing plans, OIDC onboarding for Pulumi ESC, and Connect cloud accounts onboarding, all focused on time-to-value and adoption.
   • Ship full-stack features across the Pulumi service: TypeScript/React and Web Components on the front end, Go services and REST/GraphQL APIs on the back end, including internal hackathon work delivered end-to-end from data model and API surface through to shipped UI.
   • Bridge design and engineering by contributing production code alongside design deliverables, in Figma for systems and specs, and in the real stack for prototypes that scale to ship.
   • Build and evolve design systems for complex, technical user audiences, with Figma libraries and tokens kept in sync with the Pulumi Design System's Web Components and design tokens.
   • Run research for platform engineers, DevOps/SRE, and application developer personas: internal stakeholders, then customer support and sales, then customer calls recorded with Clari Copilot, reviewed and worked through with engineers and product managers.
   • Led UX for Pulumi Insights (now Governance) from public preview through GA: cloud asset search, governance, policy-on-discovered-resources, and AI-assisted natural-language queries across AWS, Azure, GCP, and hundreds of other providers.

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. That became the foundation underneath the 10,000+ touchpoint adoption that followed. The consolidation would not have happened without it.
   • Authored the UX migration strategy to consolidate local and third-party components into a unified design system, reducing fragmentation and improving velocity.
   • Managed a cross-functional v-team of engineers using agile/scrum methodology, driving design system adoption across Eightfold's AI-powered talent intelligence platform.
   • 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

   • Supported Immersive Reader scaling from zero to 46M MAU across multiple platforms by creating a React prototype that scaled directly to production, then helping shape the public Immersive Reader SDK (github.com/microsoft/immersive-reader-sdk), a full-stack embed surface that pairs a JavaScript/TypeScript client library with the Azure Cognitive Services token exchange so any web experience could embed the reader behind a few lines of code.
   • Made Immersive Reader embeddable in any app: wrote the SDK's Python, Java, Android, and iOS quickstarts and readied them for its 2020 general availability as an Azure Cognitive Service, now embedded by 40+ partners including Canvas, Schoology, and Code.org.
   • Drove success within architecture of OneNote web application accessibility features, achieving SLA attainment of Level-C accessibility standards.
   • Implemented Microsoft Teams Assignments as an embedded web app for iOS and Android (Electron, CocoaPods, React Native), holding the visual detail and working with partner teams across Microsoft to ship the product Microsoft Classroom evolved into.
   • 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.
   • 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: full-stack work across REST API contracts, OAuth flows, and the React/TypeScript surface above them.
   • 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, including the early API surface that later became the public Immersive Reader SDK.

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)

   Through 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. Beneficialmedia · Designer · Creative Technologist

    Ongoing · Elko, NV

    • Create experiences on demand with agent harness workflows, applying systems design and visual acuity to every result.
    • Run an AI-native design and engineering practice: Figma for systems work, the full Adobe ecosystem (Photoshop, Illustrator, After Effects, Premiere, InDesign) for editorial and motion, and GenAI tools (Midjourney, Firefly, ComfyUI, Runway, ElevenLabs) wired into repeatable, brand-conditioned pipelines.
    • Maintain a portfolio site (beneficialmedia.com) built and shipped in this same loop: Next.js, TypeScript, Tailwind, MDX, Vercel, designed in Figma, built with an agent in the editor, deployed continuously.

Earlier: Microsoft, Senior User Experience Designer · Aquent, Design Integrator (Office Mix · Microsoft) · Aquent, Visual Designer · Creative Technologist (Amazon Advertising) · Aquent, Design Integrator · Prototyper (Microsoft Fresh Paint) · Metia, Interactive Designer (Microsoft account)