Product Designer, Benefits

About the Role:

We’re hiring a Senior Staff Product Designer to define, ship, and scale a new Benefits product area. In this role, you’ll design the software to service experience, with a focus on the role AI will play to connect the digital experience, support, sales and operations teams while maintaining the warmth and clarity customers expect from Gusto. 

You’ll operate at two altitudes: set the north star vision for an emerging area, then drive an MVP and fast iterations that prove value, de‑risk, and lay the groundwork for rapid scale. You’ll collaborate with Product, Engineering, and Data to design agentic workflows (what the system does), human-in-the-loop moments (what experts do), and clear decision policies for when to automate, escalate, or pause. Your work should measurably reduce customer effort, increase accuracy and compliance, and bend cost-to-serve down while keeping the experience warm and trustworthy.

About the Team:

Product Design at Gusto is a multidisciplinary team of designers, researchers, writers, and front-end developers creating intelligent, human-centered experiences for small businesses and their teams. We use data, empathy, and craft to make complex systems like payroll and benefits feel clear, capable, and kind.

Gusto is defining what it means to be an AI-native company, and Product Design is at the center of that transformation. We’re moving fast, experimenting boldly, and shaping how intelligent systems can empower our small business customers. Designers here have the autonomy to influence both how we work and what we build—accelerating our customers’ progress and helping them reconnect with the missions that drive their work.

If you’re passionate about crafting the next era of product design and helping small businesses harness the power of AI, come join us.

Here’s what you’ll do day-to-day:

• Chart the path forward: Drive 0→1 strategy for a new product area, creating a north star that shows how humans and AI collaborate to deliver accurate, empathetic, and scalable experiences for small businesses.
• Design experiences that empower: Define first principles approach to help teams decide when automation should act, when people should lead, and how systems learn over time.
• Bridge software and service: Partner with CX and Operations to design a human + AI service model where AI is the connective tissue that streamlines workflows, reduces cognitive load, and prepares the system for rapid scale.
• Partner to make it real: Work across Gusto to collaborate with Product, Engineering, and Data to define and execute your strategic vision. Build systems and rituals to prototype, evaluate, and safely scale AI capabilities.
• Elevate the bar: Work fluently with AI as a design material. Shape design systems and evaluation patterns that raise both the craft and ethics of intelligent experience design across the company.
• Measure what matters: Design for observability and feedback so every model decision can be measured, adjusted, and improved through real-world signals.

Here’s what we're looking for:

• 10+ years of product design experience, with a proven track record of leading at the product or portfolio level, including multiple 0-to-1 launches that scaled.
• Builder mindset: Hands-on craft paired with strong product sense. You’ve shipped ambitious ideas, influenced strategy, and driven alignment through design.
• Comfort with complexity: Experience creating simple, guided experiences in domains that are regulated, multi-actor, or technically dense.
• Service design fluency: Experienced in crafting end-to-end journeys where software, people, and policy work together. You see CX and Ops as co-designers, not downstream recipients.
• AI as design material: You’ve designed AI-assisted or AI-powered experiences that simplify workflows, guide decision-making, or enhance human judgment. You understand how to shape prompts, evaluate outcomes, and design for transparency, safety, and trust.
• Strategic acumen: Ability to contribute directly to business and product strategy, influence executive stakeholders, and connect design outcomes to measurable impact.
• High quality bar: Advocate for design craft and accessibility while delivering iteratively; you balance speed with raising the bar.
• Collaborative leadership: Known for mentoring senior ICs, shaping org-wide opinions, and creating leverage across teams.
• Passion for Gusto’s mission: Deep empathy for small businesses and a belief in the power of benefits to transform lives.