Head of Transportation and Parcel Strategy

at Flexport

Chicago, United States

About Flexport:

At Flexport, we believe global trade can move the human race forward. That’s why it’s our mission to make global commerce so easy there will be more of it. We’re shaping the future of a $10T industry with solutions powered by innovative technology and exceptional people. Today, companies of all sizes—from emerging brands to Fortune 500s—use Flexport technology to move more than $19B of merchandise across 112 countries a year.

The recent global supply chain crisis has put Flexport center stage as we continue to play a pivotal role in how goods move around the world. We are proud to have the support of the best investors in the game who believe in our mission, solutions and people. Ready to tackle global challenges that impact business, society, and the environment? Come join us.

The opportunity:

As the Head of Transportation & Parcel Strategy, you will lead Flexport’s parcel and trucking transportation network across the final and middle mile. You will drive end-to-end cost and speed improvements, own strategic carrier partnerships, run national RFPs, and collaborate across engineering, operations, product, and finance to build and scale a best-in-class transportation function. You’ll play a critical role in connecting our supply chain, optimizing for merchant experience, and delivering operational excellence.

You will:

Own & Optimize Carrier Operations

Lead Flexport’s middle mile (trucking) and final mile (parcel) carrier strategy, including national carriers, regional players, and brokerage partners.
Own all carrier contracts, SLAs, pricing structures, volume commitments, and QBRs.
Develop and execute Flexport’s national and global carrier strategy, ensuring speed, reliability, and margin accretion.
Build and manage deep relationships with strategic carriers (UPS, USPS, DHL, OnTrac, Veho, etc.) and hold them accountable to performance.

Run RFPs & Brokerage Expansion

Lead and execute RFPs across parcel, LTL, truckload, and regional delivery modes to improve rates and service coverage.
Stand up and scale a brokerage program to manage Flexport’s middle mile freight and backhaul opportunities.
Design and expand a zone skipping network to reduce last-mile shipping costs while improving delivery timelines.

Integrate the Transportation Network

Serve as the strategic link between inbound, fulfillment, and delivery operations to build a fully integrated supply chain.
Partner with Engineering and Product to develop carrier selection tools, automated routing logic, and marketplace integrations (Amazon, Walmart, etc.).
Own the development and execution of dedicated appointment scheduling programs for key partners like Amazon, ensuring compliance and delivery success.

Drive Cost Savings & Delivery Performance

Own Flexport’s company-wide on-time delivery (OTD) performance metrics; lead real-time and trend-based recovery programs.
Implement robust audit mechanisms for carrier invoices, reducing discrepancies and ensuring billing integrity.
Build dashboards, models, and reporting frameworks to identify opportunities to improve speed, cost, and reliability across modes.

Scale Through Mechanisms & Cross-Functional Partnership

Build SOPs, onboarding playbooks, and escalation frameworks for carrier onboarding, compliance, and expansion.
Partner closely with Legal, Finance, and Operations to ensure cohesive execution and risk mitigation.
Work with Engineering, Marketplace, and Support to identify and remove technical barriers to new carrier adoption and performance.
Act as a key voice in transportation automation, global expansion, and strategic network design.

What you’ll need:

8+ years in transportation, logistics, or fulfillment leadership roles, with direct ownership of parcel and/or trucking networks.
Proven ability to negotiate contracts, manage complex RFPs, and drive large-scale transportation strategy.
Experience building and operating a domestic brokerage program and leading middle mile trucking operations.
Expertise in zone skipping, carrier mix optimization, and delivery network design.
Deep familiarity with Amazon, Walmart, and marketplace-specific SLAs, routing guides, and appointment systems.
Strong analytical skills and experience using data to optimize for cost, speed, and customer experience.
Familiarity with TMS, shipping APIs, and parcel auditing tools.
Experience operating in a high-volume B2C or D2C eCommerce environment.
Clear and persuasive communicator, with the ability to influence senior internal stakeholders and external partners.

The range displayed on each job posting reflects the minimum and maximum target for new hire salaries for the position in the posting's respective region. Our salary ranges are determined by role, level, and location. Within the range displayed, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education and / or training.

The US base salary range for this position (this does not include bonus, equity and benefits):

$159,000—$199,000 USD

Commitment to Equal Opportunity

At Flexport, our ability to fulfill our mission of making global commerce easy and accessible relies on having a diverse, dedicated and engaged workforce. All qualified applicants will receive consideration for employment regardless of race, color, religion, sex, national origin, age, physical and mental disability, health status, marital and family status, sexual orientation, gender identity and expression, military and veteran status, and any other characteristic protected by applicable law.

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