Senior Retail Strategy & Operations Specialist

This is a fully remote position, open to applicants in New York.

📋 Description

• Provide guidance to research and engineering teams regarding merchandising, category management, assortment planning, purchasing, and retail operations.

• Recognize deficiencies in model comprehension across pricing, inventory, promotions, customer demand, store performance, and commercial strategy.

• Utilize practical retail judgment in complex situations involving products, channels, suppliers, customers, and financial targets.

• Create challenging, domain-specific tasks rooted in authentic retail practices.

• Draft precise and well-reasoned solutions related to merchandising, category management, buying, planning, and operational scenarios.

• Develop issues that necessitate commercial judgment, prioritization, data analysis, and evaluation of competing trade-offs.

• Assess AI-generated retail responses against established rubrics and scoring criteria.

• Evaluate accuracy, commercial judgment, reasoning quality, relevance, and practical applicability.

• Compare different outputs to identify superior retail recommendations.

• Detect factual inaccuracies, unsupported assumptions, weak commercial reasoning, and incomplete conclusions.

• Offer written feedback to enhance model performance.

• Develop and refine evaluation guidelines and scoring criteria.

• Engage in calibration activities alongside other retail specialists.

• Collaborate with various teams to ensure consistency and accuracy throughout the training data.

• Assist in onboarding, specialty calibration, task development, and ongoing quality review.

⛳️ Requirements

• Must be based in the United States; candidates residing in the US only.

• A minimum of 8 years of focused professional experience in retail.

• Senior-level proficiency in merchandising, category management, purchasing, planning, retail operations, or a related field.

• Experience in a recognized retailer, consumer brand, e-commerce platform, or similar organization.

• Prior experience evaluating LLM or AI-generated outputs using structured rubrics or scoring criteria is essential.

• Proven career advancement into senior manager, director, vice president, or equivalent leadership roles.

• Strong commercial judgment and capability to evaluate complex retail decisions.

• Exceptional written and verbal communication skills.

• Consistent availability for at least 35 hours per week on weekdays.

• A degree in business administration, retail management, merchandising, supply chain, marketing, economics, or a related discipline is highly relevant.

• Graduate-level education in business, strategy, operations, analytics, or management may be advantageous.

• Equivalent senior professional experience in retail strategy or operations may also be considered.

• Professional training in category management, merchandising analytics, procurement, or commercial planning may be beneficial.

• Experience with large-scale retailers, global consumer brands, or high-growth e-commerce enterprises.

• Background in omnichannel retail, marketplace operations, inventory planning, or store operations.

• Experience in developing 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.

• Immediate availability is preferred.

🏝️ Benefits

• Full-time W-2 contingent employment arrangement.

• Fully remote work.

• Competitive hourly compensation.

• At least 35 hours per week during weekdays.

• Immediate availability preferred.

• Remote consulting opportunity.

• Opportunities for onboarding, specialty calibration, task development, and ongoing quality review.