Head of Transportation

About The Role We are seeking an experienced, strategic, and data-driven Head of Transportation to lead our comprehensive transportation operations. In this critical leadership role, you will own the strategy, performance, and structure of our 3rd-party parcel network, our 1P/3P van network, and international trade compliance. Overseeing a substantial transportation budget and leading a dedicated team of over 50 personnel, you will define how high-value luxury goods move into, within, and out of our network. The ideal candidate is a strong operator and team leader with an analytical mind and innovation track record. What You Get To Do Every Day Strategic Network Leadership: Direct and optimize TRR’s multi-modal transportation network, managing a large-scale transportation budget to successfully balance cost-to-serve, speed, and premium quality. Manage and negotiate with third-party carriers (small parcel and LTL) to continue to evolve strategic partnerships in logistics. Lead 3rd-Party Parcel Operations: Own the parcel strategy across international, national and regional carriers. You will lead complex vendor negotiations, monitor carrier health, and ensure exceptional delivery standards for high-value shipments. Manage 1P/3P Van Network: Oversee our growing fleet operations, managing a team of 50+ personnel to ensure efficient, secure, and white-glove service for first-mile consignment pickups and store deliveries. Drive International Trade Compliance: Oversee global shipping compliance, ensuring all cross-border freight and international parcel shipments strictly adhere to global customs regulations, duties, and trade policies. Partner to build out cross-border solutions and operating models. Deliver on KPIs: Hold ultimate accountability for hitting and exceeding critical parcel and transportation KPIs, specifically focusing on service levels, cost per shipment, delivery quality, and people engagement metrics. Drive Innovation & Tech Integration: Partner closely with our Product, Engineering, and Technology teams to build, implement, and scale new transportation capabilities, routing optimization tools, and TMS platforms. Cross-Functional Collaboration: Act as the strategic transportation partner to Sales, other Operations teams, Finance, and Client Services leaders, ensuring our logistics strategies align with broader business objectives. What You Bring To The Role Minimum Requirements: 10+ years of total experience; 2-3 years in management consulting, finance, or similar analytical role a plus Previous experience in ecommerce fulfillment, reverse logistics, microtransit, retail transportation, or general supply chain operations Strong expertise in transportation contract negotiation International transportation and trade experience Demonstrated ability to manage operational details and execution, while also understanding the big picture Experience with quantitative analysis and modeling, creative problem solving, and complex cross-functional project management Ability to work in ambiguous environments, bring structure, prioritize, and drive results Excellent spreadsheet and presentation-building skills Preferred Requirements: Experience with scaling and building strategy within a logistics, direct-to-consumer business Experience with Google Suite (Docs, Sheets, Slides) Ability to travel up to 25% Compensation, Benefits, + Perks Employee Stock Purchase Plan 401K with Company Match Medical, Dental & Vision Insurance Paid Parental Leave 9 Paid Company Holidays Flexible Time Off (With Manager Approval) Find out more about our Benefits here. The expected salary range for this role is $160,000.00-$190,000.00. To determine starting pay we carefully consider a variety of factors, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal parity. Additionally, salary is just one component of TRR’s total rewards package. Depending on role, employees may also …

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