Staff Product Designer, Benefits

Gusto, Inc.•San Francisco, CA

6h•$146,000 - $222,000•Hybrid

About The Position

We’re hiring a Staff Product Designer for our Benefits team to design and launch a new product offering at Gusto. Our focus in Benefits is simple: help small businesses and their employees get access to better quality care at more affordable rates—in other words, we make benefits work harder for small businesses. Benefits is a notoriously complex space, full of confusing choices, high stakes, and fragmented experiences across employers, employees, carriers, and brokers. In this role, you’ll partner closely with Product Managers, Engineers, Data Science, CX, Operations, and Sales to turn that complexity into experiences that feel clear, human, and trustworthy—from end-to-end journeys to the underlying systems that power them. This is an opportunity to shape a new part of Gusto’s Benefits offering and deliver meaningful, tangible impact for small businesses and the people who rely on them.

Requirements

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

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.