Remote | Senior Retail Strategy & Operations Specialist — $55–$75/hour

24-Mag • New York, NY

2d • Remote

About The Position

This is a specialized full-time consulting opportunity for US-based senior retail professionals with deep experience in merchandising, category management, buying, planning, retail operations, and structured evaluation of AI-generated outputs. This role supports a high-impact generative AI initiative focused on improving how advanced models reason through real-world retail challenges. Selected professionals will design rigorous retail tasks, evaluate model outputs against structured criteria, develop scoring frameworks, and provide practical feedback grounded in senior-level merchandising, category, planning, and operational experience.

Requirements

• At least 8 years of dedicated professional experience in retail
• Senior-level expertise in merchandising, category management, buying, planning, retail operations, or a related area
• Experience working within a recognised retailer, consumer brand, e-commerce platform, or comparable organisation
• Prior hands-on experience evaluating LLM or AI-generated outputs using structured rubrics or scoring criteria
• Demonstrable career progression into senior manager, director, vice president, or comparable leadership responsibilities
• Strong commercial judgment and the ability to assess complex retail decisions
• Excellent written and verbal communication skills
• Reliable availability for at least 35 hours per week during weekdays
• Prior experience evaluating AI or LLM outputs against structured rubrics is required

Nice To Haves

• Experience working with large-scale retailers, global consumer brands, or high-growth e-commerce businesses
• Background in omnichannel retail, marketplace operations, inventory planning, or store operations
• Experience creating structured scoring rubrics, evaluation guidelines, or quality frameworks
• Familiarity with model training, human-feedback workflows, annotation, or AI quality assurance
• Strong understanding of pricing, assortment, promotions, forecasting, inventory, and margin management
• Experience reviewing category plans, buying strategies, merchandising proposals, or operational performance reports
• Previous collaboration with product, analytics, supply chain, marketing, finance, or technical teams

Responsibilities

• Guide research and engineering teams on merchandising, category management, assortment planning, buying, and retail operations
• Identify gaps in model understanding across pricing, inventory, promotions, customer demand, store performance, and commercial planning
• Apply practical retail judgment to complex scenarios involving products, channels, suppliers, customers, and financial objectives
• Ensure retail tasks reflect realistic business decisions and current industry practices
• Design challenging, domain-relevant tasks grounded in real retail practice
• Write accurate, well-reasoned solutions covering merchandising, category, buying, planning, and operational scenarios
• Develop problems requiring commercial judgment, prioritisation, data interpretation, and evaluation of competing trade-offs
• Ensure tasks are clear, internally consistent, and suitable for structured assessment
• Evaluate AI-generated retail responses against established rubrics and scoring criteria
• Assess correctness, commercial judgment, reasoning quality, relevance, and practical applicability
• Compare alternative outputs and determine which response provides the stronger retail recommendation
• Identify factual errors, unsupported assumptions, weak commercial reasoning, and incomplete conclusions
• Provide clear written feedback that supports improvements in model behaviour
• Develop and refine evaluation guidelines for merchandising, category management, planning, and retail operations tasks
• Define scoring criteria covering technical accuracy, commercial judgment, reasoning, and execution feasibility
• Participate in calibration activities with other retail specialists
• Collaborate across teams to maintain consistency and accuracy throughout the training data

Benefits

• Full-time W-2 contingent employment arrangement
• Fully remote role available to candidates based in the United States
• Competitive rates between $55–$75 per hour depending on expertise and project scope

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: Associate degree