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The RealReal

Head of Transportation

The RealReal

. Direct and optimize TRR’s multi-modal transportation network .

Posted 10/2/2026full-timeUnited StatesLead💰 $160,000 - $190,000 per yearWebsite

Core Competencies

Role fit
Core Competencies

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Demonstrates expertise in managing multi-modal transportation networks, optimizing logistics strategies, and ensuring compliance with global shipping regulations. Proven ability to lead teams, negotiate contracts, and drive key performance indicators in a fast-paced environment.

Highest-signal resume keywords
Transportation Contract NegotiationInternational Transportation ExperienceQuantitative Analysis and ModelingEcommerce Fulfillment ExperienceLogistics Strategy Development

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Transportation Network OptimizationBudget ManagementVendor NegotiationOperational ExecutionKPI Management
Soft Skills
Creative Problem SolvingCross-Functional CollaborationAmbiguity ManagementPrioritizationResults-Driven
Tools & Technologies
TMS PlatformsGoogle SuiteRouting Optimization Tools
Industry Keywords
Ecommerce FulfillmentReverse LogisticsMicrotransitRetail TransportationSupply Chain Operations

About the role

Key responsibilities & impact
  • Direct and optimize TRR’s multi-modal transportation network
  • Manage a large-scale transportation budget while balancing cost-to-serve, speed, and premium quality
  • Manage and negotiate with third-party small parcel and LTL carriers
  • Own parcel strategy across international, national, and regional carriers
  • Lead vendor negotiations and monitor carrier health
  • Oversee the growing 1P/3P van fleet and a team of 50+ personnel
  • Ensure efficient, secure, and white-glove service for first-mile consignment pickups and store deliveries
  • Oversee global shipping compliance, customs regulations, duties, and trade policies
  • Build cross-border solutions and operating models
  • Drive parcel and transportation KPIs including service levels, cost per shipment, delivery quality, and people engagement
  • Partner with Product, Engineering, and Technology teams on transportation capabilities, routing optimization tools, and TMS platforms
  • Collaborate with Sales, Operations, Finance, and Client Services leaders to align logistics strategies with business objectives

Requirements

What you’ll need
  • 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 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
  • 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%

Benefits

Comp & 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)
  • Bonus program eligibility, depending on role
  • Incentive pay eligibility, depending on role
  • Reasonable accommodations for individuals with disabilities