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), 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.

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.

How We Work at Wantable

• High ownership. You are trusted to make decisions that directly impact customers and financial performance.
• Hard-working and hands-on. We move fast, stay scrappy, and focus on impact.
• Independent thinkers. We value leaders who confidently make data-driven decisions without layers of approvals.
• Low bureaucracy. We avoid committees, long processes, and unnecessary steps.
• Love of fashion & product. We combine data with intuition to create experiences customers love.
• Results over pedigree. What you’ve built matters more than where you’ve been.

Benefits

Why Wantable?

• Be part of a dynamic, fast-growing company that has innovation and creativity embedded in its DNA.
• A chance to shape our customers’ journey and leave a lasting impact on their self-confidence, one order at a time.
• Join a collaborative environment where your ideas matter, your efforts are rewarded and you can see results in real time.

Wantable team members enjoy a 50% discount on food, coffee, and drinks in our HQ's beautiful Wantable Cafe. We have a laid-back, casual environment in a state-of-the-art HQ in Walkers Point.

We offer flexible schedules, paid parental leave (mothers AND fathers), and a private room for nursing mothers.

Even more exciting: paid vacation and seven paid holidays per year, plus a 50% discount on all merchandise. You’ll be eligible for the discount on your first day.

Important, but maybe less thrilling: we have ample parking, we offer medical (traditional and high deductible), dental, and vision insurance, as well as a 401K (both pre-tax and Roth options).