Product Designer, Retirement

About the company At the company, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build the company should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at the company. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. About Design at the company: Design at the company 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 the company. 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 the company and across the industry. About the Team: The Retirement team at the company builds financial products and services that help bridge the retirement gap for small business owners and their employees. With 401(k) plans designed to be affordable, easy to manage, and easy to understand, the company is working to make retirement accessible to small businesses and teams that have historically been underserved by the 401(k) market. We’re a collaborative group that values creativity, transparency, and a deep respect for our craft. We hold ourselves to a high bar and actively support one another so that we can do our best work. Our process incorporates using AI in our daily workflows to move faster, explore ideas, and increase our impact. From building tools that help individuals navigate their financial future to new retirement offerings, the Retirement team plays a central role in contributing to the company’s mission. About the Role: We’re hiring a Product Designer to partner with Product, Engineering, Data (and Research) to shape strategy, align partner teams, and create a cohesive, high-trust retirement experience across the employer and employee journey. You’ll operate as the design lead for your projects—co-owning priorities, success metrics and driving alignment across Retirement and key partner teams (Payroll, Benefits, Support/Ops). Your scope will include: Improving both setup and account management to boost confidence, adoption, and retention to reduce contact rate and confusion. Creating a more connected journey between payroll and retirement by designing across the seams of product, operations, and support—where the hardest and most interesting problems live. Designing flexible, scalable patterns across Retirement, integrating seamlessly with adjacent payroll and benefits touchpoints. Apply discerning design judgment to determine when and how to effectively incorporate AI to enhance the experience. If you’re energized by ambiguous problem spaces, high-trust financial experiences, and designing workflows that make complex decisions feel clear and confident—this role is for you. Here’s what you’ll do day-to-day: Strategic Vision & Partnership: 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. Data and research informed iteration: 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. Design Leadership & Ownership: Drive the full design process for shipped experiences—scoping and sequencing work, prototyping, testing, and delivering MVP → iteration → longer-term improvements. Trust + compliance design: Translate regulatory/tax-driven requirements into clear flows, content, and UI patterns that build trust without overwhelming customers. Communication & Storytelling: 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. Elevating Craft & Mentorship: 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. System Advocacy & Evolution: Champion the design system and contribute patterns/components that improve cohesion and quality. AI-Accelerated Prototyping & Learning: 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. Here’s what we’re looking for: We’ve found that a low ego, a growth mindset, and a bias for action go a long way here. 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 Bonus: Experience in regulated/high-trust domains (fintech, taxes, insurance, healthcare, benefits/retirement) 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 Bonus: Comfortable tackling content design aspects (making complex concepts understandable) 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 Bonus: Have contributed to growing a Design system with components or patterns Bring a cl #J-18808-Ljbffr