Job Title: Senior UX Engineer Company Name: When Job Details: $120k-$140k/yrRemoteFull,Time Job Url: https://hiring.cafe/viewjob/33fu3fb9i79jibgh Job Description: Posted 15h agoSenior UX Engineer@ WhenView All JobsUnited States$120k-$140k/yrRemoteFull TimeResponsibilities:Own UX, Architect UI, Lead AIRequirements Summary:7+ years in front-end or UX engineering; strong React/TypeScript; design systems; AI/LLM integration; analytics and A/B testing; accessible, scalable UX; excellent communication.Technical Tools Mentioned:React, TypeScript, Next.js, GraphQL, Figma AI, LaunchDarkly, Optimizely Technology Description About WhenWhen is a US-based, venture-backed company that has built a novel AI-driven health insurance marketplace and post-employment platform. Our product will transform how companies offboard employees and how people manage their transition between jobs.The OpportunityWe’re looking for a Senior UX Engineer to own and elevate the user experience across When’s platform. This is a high-impact, foundational role: you’ll define how our users interact with AI-powered tools embedded directly in the application—conversational chat interfaces, intelligent recommendations, and guided workflows that help people navigate health insurance and post-employment benefits during one of the most stressful transitions of their lives.You’ll be the driving force behind a consistent, scalable UI framework that supports data tracking and reporting, A/B testing, and outcome-based UX optimization. This isn’t just building screens—it’s architecting the front-end foundation that will power how we measure, learn from, and improve every user interaction.When is an AI-first company. We’re rapidly adopting AI across our development processes and product surface area. You’ll need to be comfortable working with and alongside AI tools daily—from prototyping with AI-assisted design and code generation to building production interfaces that wrap large language models. If you’re excited about shaping how humans and AI collaborate inside a real product, this role is for you.What You’ll DoUX Architecture & Design SystemsOwn the end-to-end user experience strategy, establishing and enforcing UX patterns, component libraries, and design tokens that ensure visual and behavioral consistency across the platformArchitect a robust, extensible UI framework (React/Next.js) purpose-built for embedded AI chat interfaces, contextual assistance panels, and conversational UX flowsDefine and maintain a living design system that bridges design and engineering, reducing duplication and accelerating feature deliveryFuture-proof our front-end architecture so new features, partner integrations, and AI capabilities can be added without reworkAI-Embedded Product ExperiencesLead the UX design and implementation of AI chat tools embedded within the application—guiding users through COBRA elections, ACA marketplace enrollment, and benefits decisionsCollaborate closely with engineers to translate LLM capabilities into intuitive, trustworthy user interfacesDesign interaction patterns for AI-driven features: streaming responses, confidence indicators, graceful fallbacks, and human-in-the-loop escalation pathsPrototype and iterate rapidly using AI-assisted development tools (e.g., Claude, Cursor, Figma AI) to accelerate the design-to-code cycleData, Measurement & OptimizationInstrument the UI framework with structured event tracking and analytics hooks that feed into our data pipeline for reporting and insightsBuild and manage an A/B testing infrastructure within the front end, enabling the product team to run controlled experiments on UX flows, copy, and AI interaction patternsDefine and optimize for specific user outcomes—enrollment completion rates, time-to-decision, support deflection—using data to drive iterative UX improvementsPartner with Product and Data teams to create dashboards and feedback loops that make UX performance visible and actionableCross-Functional LeadershipServe as the UX authority across engineering squads, providing guidance, code reviews, and hands-on mentorship on front-end best practicesWork directly with the VP of Product and CTO to translate product strategy into UX roadmap prioritiesEstablish UX quality standards and review processes that scale with the teamContribute to hiring and onboarding as the engineering team growsWho You Are7+ years of experience in front-end or UX engineering, with deep expertise in React, TypeScript, and modern component architecturesProven track record of building and scaling design systems or UI frameworks in a production SaaS environmentStrong experience designing and implementing conversational or chat-based interfaces—ideally involving AI/LLM integrationHands-on experience with front-end analytics instrumentation, A/B testing frameworks (e.g., LaunchDarkly, Optimizely, GrowthBook, or custom), and data-driven UX optimizationFluent in AI-assisted development workflows—you actively use tools like Claude, Cursor, GitHub Copilot, or similar in your daily work and can evaluate their output criticallyStrong understanding of accessibility (WCAG), responsive design, and performance optimizationExcellent communication skills—you can articulate UX rationale to engineers, product managers, and executives with equal clarityComfortable with ambiguity and ownership; you thrive in early-stage environments where you’re building the playbook, not following oneExperience with Next.js, NX monorepos, and/or GraphQL is a strong plusNice to HaveExperience in health insurance, benefits administration, COBRA, or regulated industries where UX clarity directly impacts compliance and user outcomesBackground building AI-powered product features (chat agents, recommendation engines, intelligent forms)Familiarity with GCP, Firebase, or BigQuery in the context of front-end analytics and event trackingExperience at an early-stage startup (<50 employees) where you owned the UX function end-to-endContributions to open-source design systems or component librariesPreferred locations: Chicago IL. US-based, remoteCompensation & PerksCompetitive base salary + equity100% company-paid health insuranceHigh-visibility role with direct exposure to company leadership and product strategyOpportunity to define the UX practice and AI interaction paradigm from the ground upCollaborative, mission-driven team that values craftsmanship and impactThe salary range for this position is: $120,000 - $140,000. When considers a variety of factors when determining base compensation, including experience, qualifications, and geographic location. Actual compensation will vary based on these considerations. About the Company When is a US-based, venture-backed company that has built a novel AI-driven health insurance marketplace and post-employment platform. Our product will transform how companies offboard employees and how people manage their transition between jobs.