Director, Transportation - Strategy & Network Planning

At Chewy, taking care of pets and the people who love them through the highs, the lows, and the everyday is what drives us. Grounded in that purpose and focused on our mission to be the most trusted and convenient destination for pet parents and partners everywhere, we work every day to help people feel more confident, supported, and capable in caring for the animals they love—showing up with the products, services, care, and guidance they need, whenever they need it. Bringing that to life takes exceptional leaders. Leadership at Chewy is guided by our Operating Principles, which define how we lead, make decisions, develop talent, serve our customers, and grow our business. We value leaders who think strategically, stay close to the customer, and aren't afraid to roll up their sleeves alongside their teams. They solve complex challenges, build high-performing organizations, and partner closely with senior leaders to shape the future of Chewy. If you're energized by building, leading, and making a meaningful impact, this leadership opportunity may be the right fit for you. Our Opportunity Chewy is seeking an experienced and strategic Director, Transportation Strategy & Network Planning to define and own the long-term strategy for Chewy’s transportation network planning, network design, carrier strategy, and transportation capabilities. This leader will establish the multi-year vision and operating mechanisms required to optimize transportation cost, service, speed, capacity, reliability, and customer experience while enabling Chewy’s long-term growth. The Director will own the five-year transportation strategy and capability roadmap, translating enterprise growth, customer, and financial objectives into clear network, carrier, planning, and investment strategies. This role will have significant influence over network strategy, capability development, portfolio prioritization, and transportation planning. The Director will make and influence complex decisions requiring tradeoffs across cost, speed, service, capacity, customer experience, operational complexity, and long-term flexibility. The Director will lead a high-performing organization responsible for transportation strategy, network planning, programs, and capabilities and will partner closely with Transportation Operations and third-party carriers to translate strategy into executable operating plans. This leader will also work across Fulfillment Center Operations, Engineering, Technology, Product, Delivery Experience, Customer Care, Finance, Procurement, HR, and other enterprise functions to establish priorities, secure investment, and drive alignment. A successful leader will consistently demonstrate Chewy’s Operating Principles, particularly Customers First, Act as an Owner, Operate at Depth, Deliver Results, Earn Trust, and Debate Openly; Commit Fully. This leader must be comfortable operating autonomously in a highly complex environment, making consequential decisions with imperfect information, and creating alignment across teams where direct authority is distributed. What You’ll Do Define and own Chewy’s long-term transportation strategy, translating enterprise growth, customer, and financial objectives into network design, carrier, mode, capacity, planning, and capability strategies. Own the five-year transportation strategy and portfolio roadmap, defining the physical, operational, analytical, and technology capabilities required to support Chewy’s future transportation network. Establish the strategic direction for transportation network planning, including supply and capacity planning, equipment requirements, carrier and mode strategy, network connectivity, and short-, mid-, and long-term planning horizons. Make and influence complex network decisions across cost, speed, service, capacity, reliability, customer experience, operational complexity, and long-term flexibility. Establish clear principles, analytical frameworks, and mechanisms for evaluating these tradeoffs. Develop and maintain an integrated transportation portfolio roadmap, prioritizing physical, operational, analytical, and technical enhancements based on customer impact, financial value, network requirements, and enterprise priorities. Partner with Transportation Operations to translate long-term network strategy into executable operating plans while maintaining ownership of network design, planning strategy, capability roadmaps, and optimization frameworks. Establish and own transportation performance mechanisms across cost, transit time, delivery reliability, capacity, carrier performance, and customer experience. Identify structural opportunities and drive actions when performance does not meet expectations. Develop business cases and investment strategies for major network and capability changes, incorporating financial return, customer impact, operational feasibility, capacity, risk, and long-term strategic value. Use advanced analytics, modeling, and simulation to improve decision making, understanding customer, network, and carrier behavior and translating those insights into clear business, operational, and technical improvements. Catalyze innovation across the transportation network by understanding industry trends, emerging carrier capabilities, technology advancements, and evolving customer expectations. Challenge conventional approaches and identify opportunities to create structural competitive advantage. Influence senior leaders across Operations, Finance, Technology, Product, Procurement, Customer Experience, and other enterprise functions to establish priorities, resolve complex tradeoffs, secure investment, and drive alignment around transportation strategy. Build strategic relationships with third-party transportation providers, engaging senior carrier leadership to influence capabilities, network design, service models, capacity strategies, and long-term partnership opportunities. Build and lead a high-perform