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.
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
Salary
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.
How to Apply
To apply for this role, click the "Apply for Senior UX Engineer" button on the job posting page.
Application Link
/postings/when-senior-ux-engineer-9eaaad35-ea60-4591-8e3a-e40d8710ca6b/applicants/new