Principal Product Designer, CoreX AI

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k) s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve.

Learn more about our Total Rewards philosophy.

About the team:

We’re a team of 80+ designers, writers, researchers, and systems thinkers devoted to building experiences that feel both intelligent and human. We observe language as the connective tissue between people, products, and intelligence.

If designing experiences where AI works with people—anticipating needs, explaining decisions, and amplifying empathy—lights you up, you’ll thrive here.

About the 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. You’ll define how AI works, behaves, and earns trust across the Gusto platform – starting with Gus, our AI conversational assistant, and expanding into AI-powered workflows embedded in payroll, benefits, HR, and beyond. You’ll shape the interaction model, UX principles, and product direction for AI across Gusto.

You will work with senior Product and Engineering leaders to define our AI portfolio. You will develop important AI features that customers will consider. These features will help customers finish their tasks faster and build their trust in Gusto.

This role is both strategic and hands‑on. We’re looking for someone who can set a long‑term UX vision for AI and turn it into real, shipped product that meaningfully improves how small businesses get work done.

Here’s what you’ll do day‑to‑day:

• 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 principles that teams across Gusto can adopt.
• Write and iterate on prompts in collaboration with engineering, PM, and content design.
• Prototype AI experiences using modern AI‑native tools.
• Mentor designers on the AI team and coach designers across Gusto who are shipping AI features.
• Advocate for high‑quality, responsible AI experiences across Design and R&D.

Here’s what we're looking for:

• Proven AI product impact: You’ve shipped LLM-driven product experiences to production and can demonstrate measurable impact on adoption, efficiency, or user trust.
• Systems-level thinking: You’ve designed complete AI workflows – not just chat interfaces – and can speak fluently about failure modes, guardrails, user control, and transparency.
• Strategic product influence: You’ve defined UX direction at a portfolio or company level and influenced roadmap, scope, and sequencing decisions in partnership with senior PM and Engineering leaders.
• Technical fluency: You’re comfortable collaborating with highly technical AI engineers. You understand concepts like retrieval, context management, latency, and model reliability, and can translate them into robust UX decisions.
• Builder mindset: You ship. You prototype. You iterate. You’re not interested in defining principles without turning them into real customer impact.
• Organizational leadership:
  You have enhanced team work quality. You achieved this by coaching team members, setting new standards, and building solid partnerships across different functions.

At Gusto, we strive to provide rewards that empower employees to achieve their financial and personal goals. We offer competitive compensation packages with a strong emphasis on equity based compensation (ownership in Gusto). To learn more about…