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Head of Transportation and Parcel Strategy

Flexport is a technology-driven freight forwarder transforming global trade. We are seeking a Head of Transportation & Parcel Strategy to lead parcel and middle-mile trucking strategy, optimize carrier operations, run national RFPs, scale brokerage capabilities, and partner across engineering, operations, product, and finance to improve cost, speed, and reliability across the network.

Skills

  • 8+ years leading transportation, logistics, or fulfillment networks
  • Proven contract negotiation and RFP management experience
  • Experience building and operating a domestic brokerage program
  • Expertise in zone skipping, carrier mix optimization, and network design
  • Deep familiarity with Amazon, Walmart, and marketplace SLAs and routing guides
  • Strong analytical skills and experience using data to optimize cost and speed
  • Familiarity with TMS, shipping APIs, and parcel auditing tools
  • Experience in high-volume B2C/D2C eCommerce environments
  • Strong cross-functional communication and stakeholder influence

Responsibilities

  • Lead carrier strategy for middle mile (trucking) and final mile (parcel) including national and regional carriers and brokers
  • Own carrier contracts, SLAs, pricing structures, volume commitments, and quarterly business reviews
  • Design and run RFPs across parcel, LTL, truckload, and regional delivery modes
  • Stand up and scale a domestic brokerage program and backhaul initiatives
  • Develop and expand zone skipping and carrier mix strategies to reduce last-mile costs and improve delivery timelines
  • Integrate transportation strategy with inbound, fulfillment, and delivery operations
  • Partner with Engineering and Product on carrier selection tools, routing logic, and marketplace integrations
  • Own company-wide on-time delivery (OTD) metrics and lead recovery programs
  • Implement invoice audit mechanisms and ensure billing integrity
  • Build dashboards, models, SOPs, onboarding playbooks, and escalation frameworks for carrier management

Education

  • Bachelor’s degree in supply chain, logistics, business, engineering or related field preferred
  • Advanced degree (MBA or MS) is a plus but not required
  • Relevant equivalent experience accepted

Benefits

  • Comprehensive health, dental, and vision coverage
  • 401(k) retirement plan with employer match
  • Equity / stock options
  • Generous paid time off and parental leave
  • Professional development and training budget
  • Flexible and hybrid work arrangements
  • Commuter benefits and wellness programs
To read the complete job description, please click on the ‘Apply’ button
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Dave Clark | Ryan Petersen
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Average salary estimate

$210000 / YEARLY (est.)
min
max
$160000K
$260000K

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Flexport Inc. is an American multinational corporation headquartered in San Francisco. We focus on supply chain management and logistics, including order management, delivery, trade financing, insurance, freight forwarding and customs brokerage.

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FUNDING
DEPARTMENTS
SENIORITY LEVEL REQUIREMENT
TEAM SIZE
SALARY RANGE
$160,000/yr - $260,000/yr
EMPLOYMENT TYPE
Full-time, hybrid
DATE POSTED
September 2, 2025
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