Staff Product Designer, Retirement

Gusto is on a mission to grow the small business economy by providing payroll, health insurance, and 401(k) services. They are seeking a Staff Product Designer to partner with teams across Product, Engineering, and Data to create a cohesive retirement experience, focusing on improving user journeys and integrating AI into design processes.

Responsibilities:

• Partner with Product Management to define the customer problems to solve, the strategy to solve them, and the measurable outcomes that matter—across activation, engagement, and retention
• Collaborate with Data and Research to understand funnel drop-offs, behavior over time, retention drivers as well as define success metrics and iterate based on what you learn
• Drive the full design process for shipped experiences—scoping and sequencing work, prototyping, testing, and delivering MVP → iteration → longer-term improvements
• Translate regulatory/tax-driven requirements into clear flows, content, and UI patterns that build trust without overwhelming customers
• Craft compelling product narratives that align cross-functional stakeholders around the problem, strategic options, and tradeoffs, clearly explaining the reasoning behind design decisions and outcomes
• Provide thoughtful critique and mentorship to design peers; raise the quality bar across the organization. Be an innovation driver with using and designing for AI
• Champion the design system and contribute patterns/components that improve cohesion and quality
• Use AI to move quickly from concept to customer-tested artifact — building clickable, high-fidelity prototypes that generate real signal faster than traditional methods allow. Bring a clear point of view on where AI enhances the customer experience, not just your workflow, and help raise the team's fluency through your example

Requirements:

• 8+ years in product design, with a portfolio showing end-to-end shipped work and the impact it drove
• High bar for craft across interaction design, information architecture, and visual design—especially for complex, form-heavy workflows
• Demonstrable AI fluency in your design practice — not just familiarity with tools, but evidence of AI changing how you prototype, test, and ship. We'll ask you to show this, not just describe it
• Comfort moving between design and code — whether that means shipping UI improvements directly, working closely in the codebase with engineers, or using AI-assisted tools to close the gap between prototype and production
• Comfortable operating in ambiguity and shaping messy inputs into clear goals, tradeoffs, and shipped outcomes
• Building strong partnerships with Product, Engineering, and Data to prioritize, execute, and iterate
• Systems thinker who designs solutions that scale beyond one-off screens and hold up across a product ecosystem
• Bring a clear point of view, engage in constructive feedback, and help teams align quickly by clarifying tradeoffs and driving decisions forward
• Track record leading multi-workstream initiatives across teams—setting direction, unblocking partners, and shipping measurable improvements
• Experience in regulated/high-trust domains (fintech, taxes, insurance, healthcare, benefits/retirement)
• Comfort tackling content design aspects (making complex concepts understandable)
• Have contributed to growing a Design system with components or patterns