Strategy Director Jobs in Boston, MA

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-performing organization by establishing the appropriate organizational structure, hiring and developing exceptional talent, building leadership depth and succession, and creating mechanisms that establish clear accountability and consistently Deliver Results.
• Operate at Depth while maintaining strategic perspective, developing a deep understanding of network economics, carrier performance, transportation flows, capacity constraints, customer outcomes, and planning assumptions while empowering the organization to own day-to-day execution.
• Synthesize complex information into clear strategies and recommendations, communicating effectively with senior executives and translating transportation complexity into actionable business decisions.
• Lead high-impact, executive-level initiatives that enable growth, unlock incremental profitability, improve customer experience, and create scalable capabilities for Chewy’s future transportation network.

What You’ll Need

• 10+ years of progressive experience in transportation, logistics, supply chain, or network planning, including significant leadership experience in complex transportation environments.
• Deep knowledge of transportation networks across multiple modes, carrier structures, operating models, and contract structures.
• Demonstrated experience defining and implementing long-term transportation, logistics, or network strategies with significant business impact.
• Experience developing or implementing network planning, optimization, simulation, or decision-support capabilities.
• Demonstrated ability to evaluate complex systems and identify structural opportunities that may not be apparent through conventional approaches.
• Strong understanding of transportation supply, capacity, equipment, carrier economics, network design, and short-, mid-, and long-term planning.
• Proven ability to make complex tradeoffs among competing business objectives and to think systemically across cost, customer experience, speed, service, capacity, risk, and operational complexity.
• Demonstrated ability to operate effectively in ambiguous environments, establish direction where precedent may not exist, and make high-quality decisions with imperfect information.
• Proven track record of taking end-to-end ownership of complex initiatives and delivering measurable business results in fast-paced, dynamic environments.
• Strong financial and analytical acumen with demonstrated experience developing business cases, evaluating investments, modeling complex tradeoffs, and translating data into executive-level decisions.
• Demonstrated ability to perform in-depth analysis, synthesize complex information, develop compelling narratives, establish strategy, and make clear recommendations to senior business and technical leaders.
• Exceptional communication and influencing skills with the ability to engage effectively from front-line operations through senior executives.
• Demonstrated ability to build relationships and Earn Trust across functions, influence decisions outside direct areas of authority, constructively challenge perspectives, and create alignment around difficult decisions.
• Experience sponsoring and leading large, cross-functional initiatives with broad scope and material impact beyond the Transportation organization.
• Demonstrated ability to Build High-Performing Teams, including hiring and developing exceptional talent, building leadership capability, creating succession plans, establishing clear accountability, and scaling execution through others.
• Ability to Operate at Depth when necessary while maintaining strategic perspective, empowering leaders, and avoiding unnecessary dependence on the Director for day-to-day execution.
• Demonstrated ability to challenge the status quo, Think Big, identify emerging opportunities, and translate innovative ideas into scalable business capabilities.
• Relentless curiosity and a willingness to develop expertise in unfamiliar areas while rapidly building credibility with functional experts and senior leaders.
• Bachelor’s degree in Supply Chain, Logistics, Engineering, Business, Finance, or a related field; advanced degree preferred.

• The specific salary offered to a candidate may be influenced by a variety of factors including but not limited to the candidate’s relevant experience, education, and work location. In addition, this position is eligible for 401k and a new hire and annual equity grant. C08+ positions may also be eligible for annual bonus.

We offer different types of insurance and benefits, such as medical/Rx, vision, dental, life, disability, hospital indemnity, critical illness, and accident. We offer parental leave, family services benefits, backup dependent care, flexible spending accounts, telemedicine, pet adoption reimbursement, employee assistance program, and many discounts including 10% off pet insurance and 20% off at Chewy.com.

Exempt salary team members have unlimited PTO, subject to manager approval. Team members will receive six paid holidays per year. Team members may be eligible for paid sick and family leave in compliance with applicable state and local regulations.

Chewy is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, national origin, gender, citizenship, marital status, religion, age, disability, gender identity, results of genetic testing, veteran status, as well as any other legally-protected characteristic. If you have a disability under the Americans with Disabilities Act or similar law, and you need an accommodation during the application process or to perform these job requirements, or if you need a religious accommodation, please contact CAAR@chewy.com.