Senior Director, Inventory and Merchandise Planning

Reports To: Chief Commercial Officer 

Location: Milwaukee, WI (Hybrid) 

Employment Type: Full-Time, Salaried, Exempt 

About Wantable  

At Wantable, we’re redefining retail through personalization. Our membership-based model and  proprietary technology empower us to curate products that help customers discover confidence  and joy through style. 

As a data-driven fashion company, we combine human intuition with algorithmic intelligence to  deliver personalized assortments – balancing creativity, analytics, and operational precision. 

We're seeking a Senior Director of Inventory & Merchandise Planning who is obsessed with using AI, automation, and unconventional tools to reinvent how planning is done in modern retail. This role is perfect for a builder who knows planning fundamentals but is most energized by breaking old processes, experimenting with new AI-powered workflows, and scaling smarter, self-learning systems. 

About the Role

As the Senior Director of Merchandise Planning, you will own Wantable’s end-to-end planning strategy, forecasting methodology, and inventory optimization—but you’ll also push the discipline into the future, driving automation, rapid experimentation, and next-generation decision systems. Curiosity, hands-on innovation, and a willingness to rethink everything are more important than a traditional resume.

This is a high-ownership role with direct impact on growth, profitability, and customer experience. You will work in a fast-moving, low-bureaucracy environment where independent decision-making is expected and where your build-what-you-need mindset is highly valued.

What You’ll Do

Reinvent Planning Through AI & Automation

• Build the next generation of Wantable’s forecasting and planning system using AI, ML-powered demand models, LLM-based decision tools, and automated workflows.
• Prototype and test unconventional planning approaches such as agent-based simulations, predictive replenishment triggers, automated OTB updates, LLM-assisted scenario planning, and more.
• Design AI-driven tools that increase forecasting accuracy, compression speed, and planner productivity.
• Identify manual or repetitive planning tasks and aggressively replace them with automation or AI copilots.

Own Inventory & Merchandise Planning

• Lead and own all merchandise planning, allocation, and inventory management strategies to maximize revenue and margin.
• Build and maintain financial and unit-level forecasts using AI-enhanced modeling to align merchandising, product development, and operations.
• Oversee seasonal and long-range OTB plans and deploy predictive algorithms to balance growth with inventory productivity.
• Drive in-season agility using real-time data and automated alerts for reorders, markdowns, and product flow adjustments.
• Partner with Merchandising and Product Development to support Wantable’s expanding private brands using AI-powered sell-through forecasting and attribute-level demand modeling.

Lead a High-Performing, AI-Fluent Team

• Develop and coach a planning team that embraces experimentation, autonomy, and data-driven decision-making.
• Promote a culture of curiosity—where planners feel empowered to build tools, run rapid tests, and challenge legacy processes.
• Ensure the team is skilled in AI copilots, prompt engineering fundamentals, analytics tools, and automated reporting systems.

Drive Wantable's Data & Insights Evolution

• Oversee creation of AI-optimized dashboards, predictive analytics, and self-updating reporting tools.
• Collaborate closely with Data Science and Engineering to deploy new algorithms and ensure model performance is measurable and stable.
• Use AI-assisted analysis to uncover new opportunities to improve margins, reduce inventory waste, and accelerate product flow.

Requirements

What We’re Looking For

• Deep experience in merchandise planning, inventory management, or financial planning paired with a genuine passion for AI innovation.
• Strong analytical and financial skills; comfortable designing and evaluating AI-enhanced models.
• Demonstrated ability to manage complex OTB plans, margin performance, and inventory strategy in dynamic, high-growth environments.
• Hands-on familiarity with AI tools (e.g., ChatGPT, Claude, Gemini), BI platforms (Tableau, Looker),