Staff Product Designer, Benefits

Responsibilities

• Lead 0→1 discovery and design for a new Benefits product offering—from problem framing to MVP definition—grounded in real employer + employee workflows.
• Design end-to-end service experiences across employer, employee, and internal ops workflows—identifying where AI can reduce complexity while keeping decisions clear and controllable.
• Design AI-assisted decision moments that help customers choose and act with confidence.
• Design the system that makes AI safe and scalable: define objects, rules, states, and exception paths plus guardrails for when AI should defer to humans.
• Make data legible and operational: shape the information model and UX so humans and AI can collaborate—clean inputs, clear outputs, and structured handoffs that reduce errors and rework.
• Build product feedback loops that improve AI quality over time: define success metrics, evaluation signals, and human-in-the-loop review patterns to continuously tune guidance, routing, and automation.
• Design in code to ship faster: use AI-assisted dev tools (e.g., Cursor, Claude Code) to prototype and deliver production-quality UI, collaborating tightly with engineering and shaping reusable patterns.

Requirements

• Partner cross-functionally to define human-in-the-loop workflows, and set principles for fairness, privacy, and trust.
• Design with AI as a core material—prototyping, refining prompts, and integrating AI behaviors that adapt responsibly to user context. Guide teams in balancing automation with transparency and control.
• Redesign service blueprints where AI plays an active role—automating routine workflows, predicting needs, and escalating complex cases to humans with transparency and context.
• Define area strategy using measurable bets and experimentation; partner with Analytics and AI teams to track and evaluate impact.
• Scale quality through reusable patterns, thoughtful critique, and mentorship; balance exploration with delivery.
• Influence cross-functional strategy across teams; resolve complex trade-offs and guide design through ambiguity.
• Coach across teams, build onboarding and training programs, and raise the bar for craft and systems thinking.

Compensation

Cash compensation range: $146,000/yr to $183,000/yr in Denver & most remote locations, $177,000/yr to $222,000/yr in San Francisco, Seattle & New York.