Senior Director, Inventory and Merchandise Planning

Reports To: Chief Commercial Officer

Location: Milwaukee, WI (Hybrid)

Employment Type: Full-Time, Salaried, Exempt

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.

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.

• 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
  .

• 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
  .

• 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
  .

• 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.

• 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), and modern data workflows.
• A builder mindset—comfortable creating your own planning tools, KPIs, automations, and models when existing solutions are inadequate.
• A bias toward action, independent decision-making, and low-bureaucracy execution.
• A love for fashion, product, and the art + science of retail.

• Experience with ML forecasting frameworks or…