Staff Product Designer, Retirement · Gusto

Sat, 25 Apr 2026 20:56:30 GMT
Design

Gusto · Scottsdale, AZ;Denver, CO;San Francisco, CA;New York, NY;Los Angeles, CA;Seattle, WA;San Diego, CA;Toronto, Ontario, CAN - Remote · remote

About Gusto

At Gusto, 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.

We're hiring a Staff 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 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