VP, Transportation

About the Role

This is a senior leadership opportunity to shape and optimize a complex, multi-modal transportation network supporting high-volume ecommerce fulfillment. You’ll own transportation strategy across small parcel, LTL, FTL, air, and ocean, with a direct mandate to reduce costs, improve delivery speed, and elevate customer experience. The role combines network design, carrier strategy, commercial negotiation, analytics, and technology to build a more efficient transportation operation. You’ll also connect transportation economics with product development and customer-facing service offerings, leading a high-performing team while partnering closely with Product, Revenue, and Operations.

Responsibilities

• Define and execute a multi-year transportation strategy, translating strategic priorities into actionable quarterly plans and measurable outcomes.
• Design and continuously optimize the carrier network based on changing shipment volumes, lanes, pricing, service levels, and customer requirements.
• Own transportation economics across small parcel, LTL, FTL, air, and ocean, with a focus on reducing cost while improving delivery performance.
• Build, develop, and retain a high-performing transportation organization, establishing clear priorities, accountability, and opportunities for professional growth.
• Lead strategic and commercial initiatives across Product, Revenue, and Operations to improve supply chain efficiency and the overall cost structure.
• Negotiate contracts and pricing agreements with national and regional parcel carriers as well as LTL, ocean, and air freight providers.
• Own strategic carrier relationships and serve as the senior escalation point for vendor performance, commercial, and operational issues.
• Partner with Product teams to guide the development and optimization of virtual carrier network capabilities, including rate shopping, carrier selection, auditing, and rate reconciliation.
• Analyze carrier invoices, surcharges, accessorials, and performance data to identify savings opportunities and improve vendor strategy.
• Develop business cases and analyses that uncover opportunities to improve transportation processes, vendor performance, and operating economics.
• Implement transportation optimization strategies such as zone skipping, pre-sorting, postal sharing, drop-off rates, regional sorting center delivery, and direct delivery unit strategies.
• Partner with Revenue and Operations teams to develop optimized delivery services and pricing approaches that strengthen customer value and commercial growth.
• Monitor transportation market developments, carrier capabilities, pricing trends, and emerging opportunities to continuously improve the network.

Requirements

• At least 3 years of experience in a comparable senior transportation leadership position and at least 5 years of experience in a relevant high-volume logistics, transportation, fulfillment, or 3PL environment.
• Proven experience leading transportation strategy across high-volume small parcel shipping and multiple carrier relationships.
• Deep understanding of parcel carrier pricing, invoicing, surcharges, accessorial fees, and performance management.
• Experience working with regional and national carriers and leveraging multiple transportation modes to optimize rates and service levels.
• Demonstrated experience with LTL, FTL, air, and ocean transportation, with the ability to evaluate trade-offs across modes.
• Strong knowledge of transportation optimization strategies, including zone skipping, postal sharing programs, pre-sorting, regional sortation, and related cost-reduction techniques.
• Proven track record of negotiating complex carrier contracts and securing commercially favorable rates and agreements.
• Experience partnering with technology or Product teams on transportation systems, rate shopping, carrier selection, auditing, reconciliation, or optimization tools.
• Strong analytical and financial skills, with the ability to interpret detailed transportation data while maintaining a clear view of broader strategic objectives.
• Demonstrated ability to build, lead, develop, and retain high-performing teams.
• Excellent communication and stakeholder management skills, with the ability to influence senior leaders and collaborate effectively across functions.
• Strong project management and prioritization skills, with the ability to manage multiple strategic initiatives in a fast-paced, high-volume environment.
• Strategic mindset combined with strong attention to operational detail and the ability to move comfortably between long-term planning and granular cost analysis.
• Entrepreneurial, results-oriented approach with a strong sense of ownership and a willingness to challenge existing processes and drive continuous improvement.

Benefits

• Opportunity to lead transportation strategy for a rapidly growing, technology-enabled ecommerce fulfillment network.
• Senior-level ownership of a complex, multi-modal transportation operation spanning parcel, freight, air, and ocean.
• High-impact collaboration with Product, Revenue, Operations, and other cross-functional teams.
• Opportunity to build and develop a high-performing transportation organization.
• Exposure to advanced transportation technology, including AI-enabled optimization and virtual carrier network capabilities.
• Fast-paced, entrepreneurial environment that values ownership, innovation, action, and measurable results.
• Opportunity to influence customer-facing delivery services as well as internal transportation economics.
• Inclusive workplace committed to equal employment opportunity and a diverse workforce.
• Role based in the United States, with work arrangements determined according to business and role requirements.