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 be eligible for a bonus program, incentive pay and benefits.

The RealReal is the world’s largest online marketplace for authenticated, resale luxury goods, with 40 million members. With a rigorous authentication process overseen by experts, The RealReal provides a safe and reliable platform for consumers to buy and sell their luxury items. We have hundreds of in-house gemologists, horologists, and brand authenticators who inspect thousands of items each day. As a sustainable company, we give new life to pieces by thousands of brands across numerous categories—including women's and men's fashion, fine jewelry and watches, art, and home—in support of the circular economy. We make selling effortless with free virtual appointments, in-home pickup, drop-off, and direct shipping. We handle all of the work for consignors, including authenticating, using AI and machine learning to determine optimal pricing, photographing and listing their items, as well as shipping and customer service.

The RealReal is committed to providing an equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or Veteran status. We will consider qualified applicants for a position regardless of arrest or conviction records. At TRR, People Come First. That’s why diversity and inclusion are vital to our priorities as an equal opportunity employer. You can read about our Diversity Equity and Inclusion program here .

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. The employee is regularly required to sit; use hands to finger, handle, or feel and talk or hear. The employee is occasionally required to stand; walk; reach with hands and arms; climb or balance; stoop, kneel, crouch, or crawl; and taste or smell. The employee must occasionally lift and/or move up to 10 pounds. Specific vision abilities required by this job include close vision. The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job.