Staff Product Designer, Benefits

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy . About the Role: 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. About the Team: Design at Gusto is made up of over 80 creative, collaborative people who care deeply about our mission to empower small businesses and their employees. We're a cross-functional group that is always looking for opportunities to build understanding and empathy for the people who use Gusto. We don't care much about swim lanes and though we care deeply about quality and craft, we are never precious about it. We work closely with cross-functional partners in Product, Engineering, Data, and Marketing to design, build, and ship experiences that make a real difference. We believe great design can make hard things possible, even delightful. We are building an AI-native design organization — and we mean that seriously. We're looking for designers who are already working this way: using AI to prototype ideas quickly, shorten customer feedback loops, and ship quality UX directly to customers. This isn't a future aspiration — it's how we work now, and it's changing what the design role looks like at Gusto and across the industry. Here’s what you’ll do day-to-day: 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. Here’s what we're looking for: 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 transpare ... (truncated, view full listing at source)