Design Systems, Product Designer

Gusto•San Francisco, NY

6d•Hybrid

About The Position

We're looking for an AI-native Design Systems Designer to join Gusto's Builder Enablement team. This team is responsible for Workbench, Gusto's internal design system, and for ensuring that every designer and engineer at Gusto ships high-quality work with AI assistance. This role is at the intersection of design systems craft and AI-assisted workflows. You will help evolve and maintain Workbench during a significant Brand Refresh, actively building AI tooling to improve how builders interact with the system, and expanding how the design system serves LLMs and AI-assisted products. The ideal candidate is a rigorous systems thinker with strong component and token expertise who is excited about using AI tools as a core part of their workflow. While Figma is used as a helper tool, the primary deliverables are code.

Requirements

4+ years working on a product design systems team through the full lifecycle — design, implementation, documentation, and adoption.
Experience with token architecture and component API design is required.
7+ years experience working on a product design team.
Genuine experience using AI tools (Claude, Copilot, or similar) as a meaningful part of your workflow — not just experimentally.
Comfort directing AI assistance, evaluating its output, and knowing where human judgment is required.
Ability to pair effectively with engineering, understand technical plans and constraints, and contribute meaningfully to implementation decisions and code repos.
A solid understanding of WCAG AA guidelines and how accessibility considerations shape component and token decisions.
Expert knowledge of AI design tools and Figma, including complex component construction, variable and token usage, prototyping, and basic Github process.
High degree of design craft and polish, with a strong point of view about what good looks like in a design system.
Documentation expertise and the ability to educate and align peers across disciplines.
Demonstrated ability to advocate for systemic consistency while remaining collaborative and service-minded.

Nice To Haves

Experience with LLM-readable documentation, MCP servers, or AI-assisted design tooling.

Responsibilities

Design and maintain Workbench components and patterns, including complex components with variables, variants, and tokenized styles.
Own and evolve semantic and functional token architecture as we execute the Brand Refresh and move toward theming.
Work closely with our engineering team to ensure component consistency, including coded implementations — pairing on design decisions, reviewing implementations, contributing to technical plans, and committing your own PRs.
Contribute to AI tooling that helps designers and engineers use Workbench correctly — including structured documentation, storybook examples, and content that makes the system legible to LLMs.
Support product designers and engineers through Office Hours, Slack, and async review.
Document and publish design decisions, usage guidance, and component rationale.
Participate in systemic decisions about component architecture, naming conventions, and migration strategy — especially in the context of the ongoing Brand Refresh.