Senior Retail Strategy & Operations Specialist
Employment Information
Report this job
Job expired or something wrong with this job?
Job Description
Senior retail specialist evaluating AI outputs and designing structured merchandising, buying, and operations tasks. Supporting a generative AI initiative with rubrics, calibration, and practical commercial feedback.
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
- 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
- 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 stronger retail recommendations
- Identify factual errors, unsupported assumptions, weak commercial reasoning, and incomplete conclusions
- Provide written feedback to improve model behaviour
- Develop and refine evaluation guidelines and scoring criteria
- Participate in calibration activities with other retail specialists
- Collaborate across teams to maintain consistency and accuracy throughout training data
- Support onboarding, specialty calibration, task development, and ongoing quality review
Requirements:
- US-based; candidates based in the United States
- 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 experience evaluating LLM or AI-generated outputs using structured rubrics or scoring criteria is required
- Demonstrable career progression into senior manager, director, vice president, or comparable leadership responsibilities
- Strong commercial judgment and ability to assess complex retail decisions
- Excellent written and verbal communication skills
- Reliable availability for at least 35 hours per week during weekdays
- Degree in business administration, retail management, merchandising, supply chain, marketing, economics, or a related field is highly relevant
- Graduate-level education in business, strategy, operations, analytics, or management may be helpful
- 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 valuable
- Experience 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
- 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
- Onboarding, specialty calibration, task development, and ongoing quality review opportunities
Similar Jobs
Back Office & Operations Support – Minijob
Backoffice- und Operations-Unterstützung bei Growably, einer Webflow-Agentur für conversion-optimierte B2B-SaaS-Websites. Administrative, kaufmännische und organisatorische Aufgaben auf Minijob-Basis.
Client Delivery Operations Manager
Client Delivery Operations Manager overseeing Wing's account, staffing, onboarding, and launch pipeline. Driving SLAs, escalations, reporting, and cross-functional execution for a fast-growing multinational startup.
Cash Operations Technician
Cash Depot field technician managing cash operations and first-line maintenance for ATMs, Smart Safes, and AirVac equipment. Serving customers independently across an assigned territory.
Cash Operations Technician
Cash Depot technician managing cash operations and first-line maintenance for ATMs, Smart Safes, and AirVac systems. Field-based route work with customer service and equipment troubleshooting.
Infrastructure & Operations Manager
SeneGence Shopify application integration leader owning eCommerce platforms, integrations, and reliability. Leading teams and translating business requirements into scalable enterprise application solutions.
Commercial Operations Manager
Commercial Operations Manager overseeing field workflows, timelines, and process improvements for Jackson Hewitt’s national tax-preparation services. Remote US role coordinating corporate and field partners.
IT Operations Manager
IT Operations Manager leading service delivery, infrastructure, cloud, cybersecurity, and vendors for GDIT. Supporting technology solutions and mission services across the U.S. government.
ICAM Operations Engineer – Enterprise Authentication Services
ICAM Operations Engineer sustaining enterprise authentication and federation services for millions of DoD identities. Supporting GDIT’s mission-critical remote IAM operations.
Manager, Service Operations
Renewal and Reporting Team Lead overseeing Salesforce case workflows, reporting, and renewals for CVS Health’s healthcare operations. Coaching teams and improving operational processes.
Operations Manager – Last Mile
RXO Operations Manager overseeing last-mile carrier dispatch, staffing, and delivery routes. Improving logistics efficiency across remote Kansas or Missouri operations.
Advertising Operations Manager
Advertising Operations Manager optimizing digital and retail media campaigns and product feeds for Rithum’s commerce network. Building AI-assisted workflows, reporting performance, and supporting enterprise clients.
Senior Ad Operations – AdOps
Senior Ad Operations Lead managing DSP campaigns for an AI-powered advertising technology company. Optimizing delivery, performance, tracking, and programmatic media efficiency.
Senior Driver Operations Coordinator
Senior Coordinator managing recruiting, onboarding, documentation, and live-order support for Airspace’s time-critical freight logistics operations.
Driver Operations Coordinator
Operations Coordinator supporting driver recruiting, onboarding, training, and performance documentation. Coordinating mission-critical medical-device logistics for Airspace, an AI-powered freight forwarder.
Customer Operations Manager
Customer Operations Manager supporting German renewable-energy SaaS customers at Streem. Ensuring data quality, resolving issues, and driving adoption of new platform features.
Senior Process Manager, Consultant, Process Transformation
Prozessmanager bei LM IT Services, Analyse und Transformation von Geschäftsprozessen. Beratung, Automatisierung und KI-gestützte Digitalisierung für internationale Kundenprojekte.
Senior Operations Manager
Senior Operations Manager owning forecasting, logistics, inventory, and KPI reporting for ALEMI’s handcrafted Italian leather handbag brand. Driving automation and scalable operations across partners, warehouse, and stores.
Earn Operations Specialist – Onchain Direction
Earn Operations Specialist optimizing on-chain DeFi products, campaigns, and user rewards. Improving staking, redemption, and reward-claiming experiences for Binance’s global blockchain ecosystem.
Operations Coordinator
Operations Coordinator managing ocean freight bookings, documentation, tracking, and costing for Expedock’s tech-enabled workforce augmentation platform. Remote Philippines role supporting international freight operations.
Operations Associate
Operations Associate supporting customer experience, listing due diligence, and workflow improvements. CoinGecko tracks cryptocurrency data across tokens and exchanges worldwide.