Data First Jobs

Jack & Jill

Contract Design Systems Expert ($30–$90/hr) at AI data infrastructure startup

Full Time · In Office · USA

Posted Jul 25, 2026

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This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.

She will pick the best candidates from Jack's network.

The next step is to speak to Jack.

Job Title

Contract Design Systems Expert — AI Training & Evaluation

Salary

$30–$90/hr

Company Description

Well-funded AI data infrastructure startup

Job Description

Join a pioneer in human-data evaluation to teach frontier AI models the nuances of high-quality design. You will build production-grade design systems in Figma or code, evaluate AI-generated UI outputs, and define benchmarks for aesthetics and usability. This is a unique opportunity to shape how future AI systems understand creative craft.

Location

Remote

Why this role is remarkable

  • Shape the future of generative AI by training frontier models to understand "taste," aesthetics, and professional design standards.
  • Join an elite, curated community of creative technologists and designers working on funded projects for leading AI research labs.
  • Enjoy high-impact, async contract work with flexible hours while contributing to the core infrastructure layer of creative AI.

What You Will Do

  • Create and refine comprehensive component libraries, design token architectures, and pattern libraries for diverse AI product contexts.
  • Conduct deep technical evaluations of AI-generated design outputs, providing structured critiques and scoring against rigorous quality rubrics.
  • Build and implement token pipelines and coded component libraries using React and Storybook to test AI implementation fidelity.

The ideal candidate

  • Possesses 4+ years of professional experience building and owning production-grade, token-based design systems from the ground up.
  • Demonstrates expert-level proficiency in Figma (auto-layout, variables, theming) or modern front-end engineering (React, Storybook, token pipelines).
  • Has a meticulous eye for design fidelity and the ability to articulate complex technical critiques in clear, precise English.

Who are Jack & Jill?

Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.

How does this work?

  • Jack's an AI agent for job searching and career coaching. He works for you.
  • Jill is the AI recruiter working for the company. She recruits from Jack's network.
  • If it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.

We never post fake jobs

This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.

Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn't much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.

Mention you found this on Data First Jobs — it helps us bring you more roles like this.

Contract Design Systems Expert ($30–$90/hr) at AI data infrastructure startup

Jack & Jill

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