Please note, this posting is to highlight joining Right Side Up's talent collective specifically and is not representing an internal full-time role, or a current opportunity with a client.
Right Side Up is a collective of premium marketing talent, with all of the marketing chops, and none of the agency fluff. We're trusted by the most respected early-stage ventures, the fastest-growing tech companies, and well-established Fortune 500 teams to do one thing better: growth. We have over 1,400+ clients including Stitch Fix, Sephora, Yelp, Sun Basket, Crunchbase, DoorDash, Calm, and more.
About the Role
We're seeking freelance UX/UI Designers who specialize in design systems to help our clients modernize their systems for a world where humans and AI tools build side by side. Some companies call this a Design Engineer or Systems Designer; we're using UX/UI Designer, Design Systems here because it's the clearer, more searchable term for what this role actually is: a design role, not a software engineering one. This role sits at the intersection of design systems craft and AI fluency: someone who's equally comfortable untangling a token architecture in Figma and configuring the AI-tooling connections (MCP and similar) that let coding assistants read and respect that system instead of guessing at it. Contract projects typically range from ten to forty hours per week, depending on client needs and project scope, and often run as focused, timeboxed engagements rather than open-ended retainers.
Responsibilities
Audit existing design systems for structural gaps: tokens versus variables, component architecture, and missing or outdated documentation.
Resolve foundational issues (naming, token structure, variable setup) so a design system translates cleanly into documentation and code, without introducing breaking changes for engineering.
Build and maintain design system documentation, covering components, patterns, usage guidelines, and variant rules, in a structured format built for AI-fluent workflows and legible to both humans and AI tools.
Configure and maintain AI-tooling connections between design platforms (Figma, documentation platforms) and AI coding or design assistants (Claude, Claude Code, Cursor, Figma Make, GitHub Copilot, and similar), often via MCP-style integrations.
Extract undocumented institutional knowledge from designers and engineers and turn it into clear, actionable documentation.
Establish or refine governance models, contribution workflows, and success metrics so a design system stays healthy after the engagement ends.
Collaborate closely with design and engineering stakeholders, translating between the two without needing to write production code.
Stay current on evolving AI-assisted design and design-to-code workflows as the tooling landscape shifts.
Requirements
Strong experience in design systems, UX/UI design, or design engineering, with real depth at the foundational level (tokens, variables, component architecture), not just visual component work.
Genuine, hands-on fluency with AI-assisted design or coding tools, and enough technical comfort to configure AI-tooling connections rather than just use them.
Strong written communication skills. A lot of this work is turning tribal knowledge into documentation other people (and AI tools) can actually rely on.
Comfortable working independently on defined, timeboxed engagements with light day-to-day oversight.
Adaptable to different company environments, including regulated or compliance-sensitive ones where design-to-production handoffs stay manual by design.
Tools & Platforms
Figma, including Dev Mode, variables, and component architecture.
Design system documentation platforms: zeroheight preferred, with Supernova, Backlight, Frontify, or similar also valued.
AI-assisted design and coding tools: Claude, Claude Code, Cursor, Figma Make, GitHub Copilot, and other MCP-compatible platforms.
Familiarity with how design tokens map into code (CSS variables, JSON tokens, Style Dictionary-style pipelines) is a plus.
Why Right Side Up
Join a team that values expertise, flexibility, and meaningful work with some of the most innovative brands in the world.
Exciting opportunities are available now, apply today to join our network of experts!
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