Senior UX Engineer

About When

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.

The Opportunity

We'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 Do

UX Architecture & Design Systems

• Own 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 platform
• Architect a robust, extensible UI framework (React/Next.js) purpose-built for embedded AI chat interfaces, contextual assistance panels, and conversational UX flows
• Define and maintain a living design system that bridges design and engineering, reducing duplication and accelerating feature delivery
• Future-proof our front-end architecture so new features, partner integrations, and AI capabilities can be added without rework

AI-Embedded Product Experiences

• Lead the UX design and implementation of AI chat tools embedded within the application—guiding users through COBRA elections, ACA marketplace enrollment, and benefits decisions
• Collaborate closely with engineers to translate LLM capabilities into intuitive, trustworthy user interfaces
• Design interaction patterns for AI-driven features: streaming responses, confidence indicators, graceful fallbacks, and human-in-the-loop escalation paths
• Prototype and iterate rapidly using AI-assisted development tools (e.g., Claude, Cursor, Figma AI) to accelerate the design-to-code cycle

Data, Measurement & Optimization

• Instrument the UI framework with structured event tracking and analytics hooks that feed into our data pipeline for reporting and insights
• Build 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 patterns
• Define and optimize for specific user outcomes—enrollment completion rates, time-to-decision, support deflection—using data to drive iterative UX improvements
• Partner with Product and Data teams to create dashboards and feedback loops that make UX performance visible and actionable

Cross-Functional Leadership

• Serve as the UX authority across engineering squads, providing guidance, code reviews, and hands-on mentorship on front-end best practices
• Work directly with the VP of Product and CTO to translate product strategy into UX roadmap priorities
• Establish UX quality standards and review processes that scale with the team
• Contribute to hiring and onboarding as the engineering team grows

Who You Are

• 7+ years of experience in front-end or UX engineering, with deep expertise in React, TypeScript, and modern component architectures
• Proven track record of building and scaling design systems or UI frameworks in a production SaaS environment
• Strong experience designing and implementing conversational or chat-based interfaces—ideally involving AI/LLM integration
• Hands-on experience with front-end analytics instrumentation, A/B testing frameworks (e.g., LaunchDarkly, Optimizely, GrowthBook, or custom), and data-driven UX optimization
• Fluent 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 critically
• Strong understanding of accessibility (WCAG), responsive design, and performance optimization
• Excellent communication skills—you can articulate UX rationale to engineers, product managers, and executives with equal clarity
• Comfortable with ambiguity and ownership; you thrive in early-stage environments where you're building the playbook, not following one
• Experience with Next.js, NX monorepos, and/or GraphQL is a strong plus

Nice to Have

• Experience in health insurance, benefits administration, COBRA, or regulated industries where UX clarity directly impacts compliance and user outcomes
• Background 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 tracking
• Experience at an early-stage startup (<50 employees) where you owned the UX function end-to-end
• Contributions to open-source design systems or component libraries

Preferred locations: Chicago IL. US-based, remote

Compensation & Perks

• Competitive base salary + equity
• 100% company-paid health insurance
• High-visibility role with direct exposure to company leadership and product strategy
• Opportunity to define the UX practice and AI interaction paradigm from the ground up
• Collaborative, mission-driven team that values craftsmanship and impact

The 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.