Retail Specialist

Weekday AI

16h • $60 - $80 • Remote

About The Position

This role is for one of our clients. Join a leading AI research organization's advanced GenAI team and contribute your real-world retail expertise to the development and evaluation of next-generation AI models. We are seeking experienced Retail Specialists with deep industry knowledge and hands-on experience evaluating AI-generated outputs against structured criteria. You will help bring practical retail judgment to AI training data by identifying knowledge gaps, designing realistic retail scenarios, and assessing whether AI-generated responses accurately reflect professional standards and practices. This is a full-time engagement requiring approximately 35 hours per week, primarily during weekdays. The role is fully remote.

Requirements

• 8+ years of professional retail experience in areas such as merchandising, category management, buying, retail planning, retail operations, or related functions.
• Experience working within a recognized large-scale retail, consumer, e-commerce, or omnichannel organization is strongly preferred.
• Prior hands-on experience evaluating LLM or AI-generated outputs against rubrics or structured scoring criteria is mandatory. Applicants should be prepared to describe this experience.
• Demonstrated career progression and increasing responsibility, such as Category Manager → Senior Manager → Director of Merchandising or an equivalent progression.
• Strong understanding of retail strategy, merchandising processes, category performance, inventory considerations, customer behavior, and operational decision-making.
• Ability to assess complex business scenarios and determine whether recommendations are practical and commercially sound.
• Strong written and verbal communication skills, with the ability to clearly explain professional judgment and reasoning.
• Excellent problem-solving and analytical abilities.
• High attention to detail and consistency when applying evaluation criteria.
• Comfortable collaborating with cross-functional teams and other subject-matter experts.
• Ability to commit reliably to approximately 35 hours per week during weekdays.

Nice To Haves

• The ideal candidate is a seasoned retail professional who understands how decisions are made in real-world retail environments and can distinguish between an answer that merely sounds reasonable and one that reflects genuine industry expertise.
• Experience across multiple areas of retail, combined with exposure to AI evaluation, training data, structured grading, or similar quality-assurance processes, will be particularly valuable.

Responsibilities

• Work with research and engineering teams to identify and address knowledge gaps related to retail merchandising, category management, buying, planning, and operations.
• Design challenging, realistic retail tasks that reflect real-world business scenarios and decision-making.
• Develop accurate, well-reasoned solutions based on established retail practices and professional experience.
• Evaluate AI-generated responses using structured rubrics, assessing accuracy, reasoning, judgment, relevance, and completeness.
• Provide clear and actionable written feedback explaining strengths, weaknesses, and areas for improvement.
• Develop and refine evaluation guidelines and scoring frameworks specifically for retail-related tasks.
• Collaborate with other subject-matter experts to maintain consistency, accuracy, and quality across AI training and evaluation datasets.
• Help translate practical retail knowledge and decision-making processes into structured guidance that can be used to improve AI systems.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed