Staff / Principal

We are looking for an AI-native Design Systems Designer to join Gusto's Builder Enablement team, responsible for Workbench, Gusto's internal design system, and for how every designer and engineer ships high-quality work with AI assistance. This role sits at the intersection of deep design systems craft and fluency in AI-assisted workflows. You will help evolve and maintain Workbench during a mid-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 level of this role is similar to/equivalent of a Senior Staff-level.

The Builder Enablement team's mission is to make high-quality, AI-assisted shipping the default for every builder at Gusto. They own Workbench, the design system, and how it gets expressed to AI tools and builders. Work spans component design and documentation, token architecture, AI tooling (including MCP servers, prompt engineering, and eval systems), and supporting the broader design and engineering org. The team is small, tight-knit, and embedded within Gusto's design organization, led by CDO Amy Thibodeau.

• 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 engineering 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.

• Design Systems Experience: 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.
• Product Design Experience: 7+ years experience working on a product design team.
• AI Fluency: 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.
• Technical Acumen: Ability to pair effectively with engineering, understand technical plans and constraints, and contribute meaningfully to implementation decisions and code repos.
• Accessibility Minded: A solid understanding of WCAG AA guidelines and how accessibility considerations shape component and token decisions.
• Technical Skill: Expert knowledge of AI design tools and Figma, including complex component construction, variable and token usage, prototyping, and basic Github process.
• Design Integrity: High degree of design craft and polish, with a strong point of view about what good looks like in a design system.
• Communication: 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.
• Additional Experience: Experience with LLM-readable documentation, MCP servers, or AI-assisted design tooling.

Cash compensation range is $147,000/yr to $215,000/yr in Denver, and $178,000/yr to $253,000/yr in San Francisco and New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, whose physical office is in Scottsdale. The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required.

All full-time employees receive competitive base pay, benefits, and equity (RSUs).