Retail Specialist | $60-$80/hr Remote
Overview
This role places you at the forefront of generative AI, where your deep retail expertise directly improves how large language models understand and reason about the shopping world. You'll partner with a leading AI lab to design challenging retail tasks, score model outputs, and refine evaluation rubrics — all with the goal of making AI smarter and more reliable in retail contexts. It's a part-time, remote position that offers a competitive hourly rate and the chance to shape foundational AI models.
What You'll Do5
- 1Work closely with research and engineering teams to identify and fill gaps in retail reasoning — from merchandising logic to category management and day-to-day operations.
- 2Create realistic, domain-specific retail tasks and write clear, accurate solutions that reflect genuine industry practices.
- 3Assess AI model outputs against detailed rubrics, then deliver written feedback on the model's correctness, reasoning, and judgment quality.
- 4Help build and improve scoring guidelines and evaluation rubrics tailored to retail scenarios.
- 5Partner with fellow subject-matter experts to maintain consistency and high standards across all training data.
Requirements5
- 1At least 8 years of professional retail experience at a top-tier company such as Amazon, Walmart, Target, Nike, Costco, or Home Depot — ideally in merchandising, category management, buying/planning, or retail operations.
- 2Hands-on experience evaluating LLM or AI model outputs against structured rubrics or scoring criteria (this experience is mandatory and must be described in your application).
- 3A clear record of career progression — for example, moving from Category Manager to Senior Manager to Director of Merchandising.
- 4Ability to commit reliably to at least 35 hours per week during weekday business hours.
- 5Strong verbal and written communication skills, plus solid problem-solving and interpersonal abilities.
Who Should Apply
We're looking for a seasoned retail professional who has spent years in high-stakes merchandising or category management roles at industry giants. You're not just an expert in your field — you're curious about AI and excited to apply your real-world judgment to train the next generation of language models. You enjoy meticulous evaluation work, can articulate why a model's answer is right or wrong, and thrive in a collaborative, fast-paced environment.
Salary Insight
$60.00 - $80.00 per hour (part-time, W-2 employment through Cincinnatus LLC)
Application Tip
When applying, lead with a specific example of your experience evaluating AI or LLM model outputs. Describe the rubrics you used, the types of tasks you scored, and how your feedback improved model performance — this is the single most important qualification the hiring team will look for.
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