ShipMonk

Director, Transportation Strategy – Operations

ShipMonk

full-time

Posted on:

Location Type: Hybrid

Location: Fort Lauderdale • Florida • Kentucky • United States

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Job Level

Lead

Tech Stack

Go

About the role

  • Lead transportation initiatives requiring deep coordination across Operations at all sites, Transportation leadership, CX, Finance, Product, and other stakeholders.
  • Serve as the central program owner for network-wide transportation execution, ensuring consistency in rollout, adoption, and performance.
  • Build structured project plans, operating rhythms, escalation paths, and stakeholder updates to drive delivery of complex initiatives.
  • Partner directly with site leaders to ensure transportation programs align with local workflows, constraints, and network priorities.
  • Drive execution of major transportation launches, pilots, and operational upgrades across multiple locations.
  • Support long-term transportation strategy across parcel and freight, aligned with growth, service, and cost objectives.
  • Identify opportunities to strengthen carrier diversification, service levels, and network resiliency.
  • Drive strategic programs that improve merchant outcomes and operational scalability.
  • Support evaluation and implementation of TMS platforms, carrier integrations, and transportation optimization tools.
  • Partner with Product and Engineering teams to define requirements and ensure operational fit.
  • Lead change management efforts to drive adoption across sites and transportation workflows.
  • Partner with Go-to-Market and Marketing teams to ensure transportation-related launches are positioned, communicated, and executed successfully.
  • Support launch readiness planning, operational enablement, and internal training for new transportation products, carrier services, or network capabilities.
  • Ensure feedback loops between Transportation execution and market-facing teams to improve adoption and customer outcomes.
  • Develop reporting and insights around network cost, service trends, carrier performance, and operational health.
  • Build and support internal and external-facing presentations, including leadership updates, transportation business reviews, and strategic partner materials.
  • Provide data-driven recommendations that inform transportation priorities and network investments.
  • Monitor execution risks across transportation programs and lead corrective action planning.

Requirements

  • 4+ years of experience in transportation, logistics operations, supply chain strategy, or program management.
  • Proven success leading cross-functional initiatives across multiple operational stakeholders and site teams.
  • Strong analytical and communication skills, with experience translating data into business and customer-facing insights.
  • Familiarity with parcel networks, carrier integrations, and transportation technology preferred.
Benefits
  • Global Fulfillment Network: Our 12+ owned and operated fulfillment centers span the US, Canada, Mexico, the U.K., and Mainland Europe. We never outsource, ensuring quality and consistency.
  • Proprietary Technology: We've eliminated the need for tribal knowledge with our AI-powered platform. It provides a real-time, unified view of inventory and orders, giving our merchants the control and visibility they need to succeed.
  • Unrivaled Support: We provide hands-on, "mom and pop" support with a global reach. Our dedicated teams are on-site at every fulfillment center, ready to jump into action.
  • Transparent Pricing: We believe in honest, long-term partnerships. Our all-inclusive pricing means predictable costs, with no hidden fees or surprises.
  • Committed to the Future: We invest over $10 million annually in research and development to ensure our technology and services continually evolve, helping merchants plant roots with a partner who is here to stay.
Applicant Tracking System Keywords

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

Hard Skills & Tools
transportation executionproject managementdata analysistransportation optimizationcarrier integrationsupply chain strategyprogram managementchange managementreportingoperational health
Soft Skills
leadershipcommunicationanalytical skillscross-functional collaborationstakeholder managementproblem-solvingstrategic thinkingpresentation skillsadaptabilitycustomer focus