Design Systems, Product Designer

About [REDACTED]

At [REDACTED], we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build [REDACTED] should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at [REDACTED]. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

About the Role:

We're looking for a AI-native Design Systems Designer to join [REDACTED]'s Builder Enablement team — the team responsible for Workbench, [REDACTED]'s internal design system, and for how every designer and engineer at [REDACTED] ships high-quality work with AI assistance.

This role sits at an exciting and genuinely new intersection: deep design systems craft combined with fluency in AI-assisted workflows. You'll help evolve and maintain Workbench at a pivotal moment — we're 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 as much as it serves human designers. 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 how they work, not just an add-on. We use [REDACTED] as a helper tool, but our deliverables are code. The level of this role is similar to/equivalent of a Senior Staff-level.

About the Team:

The Builder Enablement team's mission is to make high-quality, AI-assisted shipping the default for every builder at [REDACTED]. We own Workbench, [REDACTED]'s design system, but we also own how it gets expressed to AI tools and builders. Our 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 in using the system well.

We're a small, tight-knit team of designers and engineers embedded within [REDACTED]'s design organization, led by our CDO, [REDACTED]. We care deeply about craft, systems thinking, and making complex things feel simple for the people who depend on us.

Product Design at [REDACTED] is made up of over 70 creative, collaborative people who care deeply about our mission to empower small businesses and their employees. We’re a cross-functional bunch focused on Design, Research, Writing, Ops and Front-end Development who are always looking for opportunities to build understanding and empathy for the people who use [REDACTED]. We don’t care a whole lot about swim lanes and we work closely with our partners in Product, Engineering, Data, and Marketing to design, build and ship experiences that make a difference. We are passionate advocates for thoughtful, crafted, and inclusive experiences and we believe great design can make hard things possible, even delightful. Read more about Design at [REDACTED].

Here’s what you’ll do day-to-day:

• 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, [REDACTED], 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

Here’s what we're looking for:

• 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 [REDACTED] 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.

Our cash compensation range for this role 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 from the amounts listed above.

[REDACTED] has physical office spaces in Denver, San Francisco, and New York City. Employees who are 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 [REDACTED] roles, [REDACTED]'s subsidiary, whose physical office is in Scottsdale.

Note: 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 [REDACTED] office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at [REDACTED].

[REDACTED] is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. [REDACTED] considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. [REDACTED] is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

[REDACTED] takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your [REDACTED] application will be subject to [REDACTED]'s Applicant Privacy Notice.