Senior Director, Inventory and Merchandise Planning (AI + Automation Focused)

Reports To: Chief Executive Officer (CEO)

Location: Milwaukee, WI (Hybrid) or Los Angeles, CA (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, Inventory and Merchandise Planning who operates at the intersection of Engineering, Data Science, and Retail Planning. We aren't looking for a traditional planner; we want a vibe coder and relentless problem-solver who is obsessed with "cracking the code" of modern retail using new systems and algorithms.

About the Role

The Senior Director, Inventory and Merchandise Planning role is designed for the independent thinker who is equally comfortable architecting a forecasting engine as they are managing a seasonal buy. You are hyper-in-tune with the latest tools and possess the "build-what-you-need" mindset required to break outdated, manual processes in favor of smarter, self-learning systems. If you are energized by high-stakes data puzzles and want to lead a high-growth transformation in a low-bureaucracy environment, you belong here.

What You’ll Do

Reinvent Planning Through AI & Automation

• Architect the Future of Merchandising: Build a self-correcting forecasting engine that handles traditional OTB (Open-to-Buy) management and inventory targets using LLM-based decision tools and automated workflows to eliminate "busy work".
• The Planning Sandbox: Approach seasonal planning and demand modeling like an engineer; use your "outside the box" thinking to prototype agent-based simulations and predictive replenishment triggers that ensure we never miss a trend.
• High-Efficiency Planning Workflows: Identify manual or repetitive tasks within the planning cycle—from margin analysis to allocation—and aggressively replace them with high-efficiency automation or AI copilots.
• Applied Mathematics & Optimization: Design tools that don’t just "report" data but use your analytical rigor to compress decision cycles, evaluate complex margin models, and maximize the team’s productivity.
• Tool-Building for Planners: Act as a hybrid creator who develops custom planning tools and KPIs when off-the-shelf solutions aren't fast or smart enough for our growth.

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 The Data 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

• The Creator Mindset: You are a builder at heart. Whether you have a background in Engineering, Mathematics, or Data Science, you have the "outside the box" thinking required to reinvent retail.
• Retail Fluency: You understand the fundamentals of merchandise planning and inventory strategy but view them through a technical lens.
• Technical Literacy: Hands-on experience with modern data workflows and AI tools (ChatGPT, Claude, Gemini) along with BI platforms like Tableau or Looker.
• Analytical Rigor: You love the math behind the business and are comfortable designing and evaluating complex, AI-enhanced models.
• Bias for Action: You thrive in low-bureaucracy environments where you make independent, data-driven decisions without needing layers of approval.
• Passion for the Product: A genuine love for fashion and the "art + science" of creating a customer experience people love.

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.

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).