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Senior Director, Inventory and Merchandise Planning (AI + Automation Focused)
Milwaukee, WI 53204
1 month ago
🤖 AI-First📈 High Growth💻 Open SourceExplicitly requires vibe coding skills; heavy emphasis on AI copilots, LLM-based tooling, rapid prototyping, and building custom planning tools.
About the Role
Senior Director, Inventory and Merchandise Planning leading the design and execution of AI- and automation-driven forecasting, inventory, and allocation systems. The role combines technical leadership, hands-on tool building, and team development to replace manual planning with self-learning models and automated workflows.
Job Description
Role
Senior Director, Inventory and Merchandise Planning responsible for owning merchandise planning, allocation, and inventory strategy while architecting AI- and automation-first forecasting and planning systems. This role operates at the intersection of Engineering, Data Science, and Retail Planning and requires hands-on tool building and experimentation to replace manual processes.
Key Responsibilities
- Architect a self-correcting forecasting engine that supports OTB management and inventory targets using LLM-based decision tools and automated workflows.
- Prototype agent-based simulations and predictive replenishment triggers for seasonal planning and demand modeling.
- Identify manual planning tasks and replace them with automation or AI copilots to improve efficiency across margin analysis, allocation, and reporting.
- Design analytical and optimization tools to compress decision cycles, evaluate complex margin models, and maximize productivity.
- Own merchandise planning, allocation, and inventory management strategies to maximize revenue and margin.
- Build and maintain AI-enhanced financial and unit-level forecasts and oversee seasonal and long-range OTB plans.
- Drive in-season agility with real-time data, automated alerts for reorders and markdowns, and predictive algorithms for product flow.
- Partner with Merchandising and Product Development on sell-through forecasting and attribute-level demand modeling for private brands.
- Develop and coach a planning team skilled in AI copilots, prompt engineering fundamentals, analytics tools, and automated reporting systems.
- Collaborate with Data Science and Engineering to deploy algorithms and ensure measurable, stable model performance.
Requirements
- Creator/build mindset with background in Engineering, Mathematics, or Data Science (or equivalent experience).
- Retail fluency and understanding of merchandise planning and inventory strategy.
- Technical literacy and hands-on experience with modern data workflows and AI tools (explicitly: ChatGPT, Claude, Gemini) and BI platforms (Tableau or Looker).
- Strong analytical rigor and comfort designing and evaluating complex, AI-enhanced models.
- Bias for action and ability to operate in a low-bureaucracy environment making independent, data-driven decisions.
- Passion for product and fashion; ability to combine data and intuition to create customer experiences.
Nice to Have
- Experience with ML forecasting frameworks or LLM workflow automation.
- Experience leading teams through rapid tooling transitions or tech-driven process reinvention.
- Comfort collaborating with data engineers and data scientists.
Location & Employment
- Locations: Milwaukee, WI (Hybrid) or Los Angeles, CA (Hybrid)
- Employment Type: Full-Time, Salaried, Exempt
- Reports to: Chief Executive Officer (CEO)
Benefits (selected)
- Hybrid work (Milwaukee or Los Angeles)
- Flexible schedules
- Paid parental leave (mothers and fathers) and private nursing room
- Paid vacation and seven paid holidays per year
- 50% merchandise discount (eligible first day)
- Medical (traditional and HDHP), dental, and vision insurance
- 401(k) with pre-tax and Roth options
- Ample parking and state-of-the-art HQ (Walkers Point)
Tech Stack
ChatGPTClaudeGeminiTableauLookerLLM-based decision toolsAI copilotsML forecasting frameworksLLM workflow automationAgent-based simulations
Skills
LeadershipTeam DevelopmentMerchandise PlanningInventory ManagementForecastingData-driven Decision-makingApplied MathematicsOptimizationExperimentationPrompt EngineeringAnalyticsCross-functional CollaborationTool BuildingAutomationProject Management
Experience Level
Employment Type
Full-time
Benefits
- •Hybrid work (Milwaukee or Los Angeles)
- •Flexible schedules
- •Paid parental leave (mothers and fathers)
- •Private nursing room
- •Paid vacation
- •Seven paid holidays per year
- •50% merchandise discount (eligible first day)
- •Medical insurance (traditional and high deductible)
- •Dental insurance
- •Vision insurance
- •401(k) pre-tax and Roth options
- •Ample parking
- •State-of-the-art HQ (Walkers Point)