Senior Product Designer, Benefits

About the Role:

We’re hiring a Senior Product Designer to design agentic benefits experiences at Gusto.

AI is transforming how people work, and we’re embracing that transformation head-on. In this role, you’ll explore how intelligent systems can anticipate, guide, and simplify the right moments while keeping humans in control. You’ll define how AI agents work with people, improving accuracy, surfacing insights, and removing friction while preserving Gusto’s clarity and warmth.

You’ll partner with Product, Engineering, Data Science, CX, and Operations to build agentic experiences and human-in-the-loop workflows that balance automation with human judgment. You’ll lead with craft, systems thinking, and imagination—turning complex workflows into intuitive, empowering experiences.

This is an opportunity to shape the future of Benefits and help define what it means for our product and company to become AI-native.

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:

• Evolve MVPs into stable, intuitive products that customers trust. Use AI to detect friction, personalize flows, and simplify repetitive work.
• Lead design across multiple surfaces or teams to scale consistent patterns and frameworks. 
• Partner with Data and Engineering to use AI for monitoring quality and personalization.
• Design experiences that combine human judgment with intelligent automation—using AI to anticipate needs, simplify decisions, and keep people in control.
• Own end-to-end AI-powered experiences that solve real customer problems—defining where intelligence enhances clarity, personalization, and trust.
• Use AI tools to ideate, generate, and test design concepts rapidly. Translate findings into clear, testable designs.
• Apply fairness, transparency, and empathy when designing AI-driven features.

Here’s what we're looking for:

• • 5–8 years of product design experience, demonstrating the ability to ship and launch complex end-to-end Experiences
  • Product Design Expertise: Design complex, end-to-end experiences that balance speed, quality, and measurable outcomes.
  • AI as Design Material: You design AI-assisted experiences that simplify workflows, guide decisions, or enhance human judgment. You shape prompts, test outputs, and design for clarity and trust in every interaction.
  • Systems Thinking: You extend components responsibly and contribute patterns tied to real business needs.
  • Service Design Orientation: You design journeys that connect people, policy, and AI systems—identifying seams between automated and human touchpoints and creating experiences that hand off seamlessly with clarity and empathy.
  • Craft & Quality: You set a high bar for design execution, accessibility, and polish across your product area.
  • Collaboration & Influence: You build strong partnerships with PMs, Engineers, and Data Scientists; create alignment within your team.