Head of Transportation and Parcel Strategy

About Flexport:

At Flexport we believe global trade can move the human race forward. Thats why its our mission to make global commerce so easy there will be more of it. Were shaping the future of a $10T industry with solutions powered by innovative technology and exceptional people. Today companies of all sizesfrom emerging brands to Fortune 500suse 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 Flexports 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. Youll play a critical role in connecting our supply chain optimizing for merchant experience and delivering operational excellence.

You will:

Own & Optimize Carrier Operations

• Lead Flexports 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 Flexports 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 Flexports 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 Flexports 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 youll 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.