Design System Specialist - AI Trainer

DataAnnotation is looking for an experienced Design System Specialist - AI Trainer to evaluate how frontier AI models handle real visual design work: interfaces, layouts, typography, and visual systems. You bring the eye you have already built over a career of shipping design. We bring design problems the models cannot yet solve on their own. In this role, you will design a challenging, realistic brief drawn from your own practice - a landing page, a pitch deck, a data visualization, a poster, a motion piece - then run it through frontier AI design tools and evaluate what comes back against a professional standard. This is a new and growing area for our company, focused on teaching AI to better understand visual and design principles. These projects span UI/UX critique, product visuals, and aesthetic evaluation, including presentations and creative deliverables. Your taste, your craft standards, and the written rationale behind them become the signal that shapes the next generation of design tools. Advantages of contracting with us: You will be able to choose which projects you want to work on and when. You work on your own schedule, on your own computer, from the comfort of your own home. Projects are paid hourly up to $75-$125 USD per hour, with bonus rates available on some projects. Responsibilities: Design challenging, realistic design briefs drawn from your own professional expertise. Run those briefs through frontier AI design tools and evaluate the output against the standard you would hold a colleague to. Compare two model versions on identical prompts and assets, and make the call on which performed better and where each fell short. Critique model-generated interfaces, mockups, layouts, slides, infographics, illustrations, and motion. Flag concrete failures with evidence: alignment and spacing, content overflow and cutoff, typography, visual hierarchy, SVG and illustration quality, ignored assets, off-brief interpretation. Contribute across software and interactive work, office and presentation design, technical illustration, graphic design, and new media. Qualifications: Fluency in English (native or bilingual level). Background in UI/UX design, web design, product design, or graphic design. Strong understanding of visual hierarchy, layout, typography, interaction design, and user flow. The ability to articulate why a design fails, not only that it does. Working comfort with AI design tools, or the ability to pick them up quickly. A current, in progress, or completed Bachelor's is preferred but not required. Note: Payment is made via PayPal. We will never ask for any money from you. PayPal will handle any currency conversions from USD. Only applicants in Australia, Canada, Ireland, New Zealand, the United Kingdom, and the United States will be considered for this role. This is an independent contractor position.