Principal Product Designer - AI

4w1 month ago

Gusto

New York City, US · Full-time · $204,000 – $280,000

About this role

We're hiring a Principal Product Designer to lead AI design across Gusto. This is one of the most senior individual contributor design roles at the company, where you'll define how AI works, behaves, and earns trust across the Gusto platform.

You'll shape the interaction model, UX principles, and product direction for AI across Gusto, starting with Gus, our AI conversational assistant, and expanding into AI-powered workflows embedded in payroll, benefits, HR, and beyond. Day-to-day, you'll design full AI-powered workflows, partner with AI Product and Engineering leaders, and establish scalable AI interaction patterns.

Design at Gusto is made up of over 80 creative, collaborative people who care deeply about our mission to empower small businesses and their employees. We are building an AI-native design organization — using AI to prototype ideas quickly, shorten customer feedback loops, and ship quality UX directly to customers.

This role is both strategic and hands-on. You'll set a long-term UX vision for AI and turn it into real, shipped product that meaningfully improves how small businesses get work done, while building their trust in Gusto.

Requirements

Proven experience as a Principal or Staff-level Product Designer, with a focus on AI or conversational interfaces.
Deep expertise in designing AI-powered workflows, including input, validation, and handling of risk and uncertainty.
Strong portfolio demonstrating shipped AI features or conversational experiences that earned user trust.
Ability to set a long-term UX vision for AI and execute hands-on from concept to launch.
Experience partnering with AI Product and Engineering leaders to navigate technical constraints.
Fluency with AI tools and a demonstrated practice of using AI to prototype and iterate quickly.
Track record of designing for complex, regulated domains (e.g., payroll, benefits, HR) is a strong plus.

Responsibilities

Define and evolve the UX vision for our Gus conversational assistant and AI experiences across the Gusto platform.
Lead and ship Tier 1 AI initiatives from early concept through launch and iteration.
Design full AI-powered workflows – shaping how users provide input, how model outputs are validated and acted on, and how the experience handles risk, uncertainty, and failure.
Partner closely with AI Product and Engineering leaders to translate complex technical constraints into intuitive, credible user experiences.
Establish scalable AI interaction patterns and design systems for AI features across the product.
Develop high-impact, customer-facing AI capabilities that help customers finish tasks faster and more effectively.
Work with senior Product and Engineering leaders to define the AI portfolio and product direction.

Benefits

Competitive base pay, benefits, and equity (RSUs) — everyone who helps build Gusto shares in its success.
Opportunity to shape AI design at a company serving over 500,000 small businesses nationwide.
Work with a cross-functional team of over 80 designers who care deeply about craft and mission.
AI-native design environment where you'll use cutting-edge tools daily to prototype and ship.
Flexible location with teams in Denver, San Francisco, and New York.