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Chicago - VP Intermodal
Chicago, Illinois, United States
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Work Model: Remote/Field Based (Heavy Travel)

Work Schedule: Monday–Friday, standard business hours

Travel Requirements: Up to 60%

Supervisory Responsibilities: Yes, oversight of 6 employees

Reports to: Chief Commercial Officer

Intermodal leverages the company's Intermodal portfolio of service offerings and capabilities to solve complex supply chain and logistics challenges for prospective and existing clients. This role is responsible for designing and executing plans to meet new business sales targets while building and deepening relationships with current and potential customers across the intermodal vertical.



  • Design and execute a territory sales plan to achieve and exceed new net revenue growth targets within the Intermodal vertical.
  • Build and strengthen relationships with prospective and existing customers, effectively communicating the company's Intermodal value proposition.
  • Use a consultative approach to guide prospects through the buying cycle, developing formal, written sales solutions to close business.
  • Navigate complex buying committees while maintaining professional relationships with economic buyers and key executives within target accounts.
  • Partner cross-functionally with Global Solutions, Client Services, Procurement, Operations, Legal, Finance, and IT to deliver world-class client solutions.
  • Accurately forecast and maintain opportunities within Salesforce, driving issues to closure with urgency and resolving client objections.
  • Bachelor's degree in business administration, engineering, technology, or a related field.
  • 10+ years of sales experience, including selling multi-modal 4PL/managed transportation/TMS solutions with a $1M+ annual quota.
  • Proven track record as a strategic enterprise sales executive growing new business, with experience prospecting and managing a full sales cycle.
  • Experience with TMS, supply chain, and logistics technology tools preferred.
  • Strong consultative and value-based selling skills, with the ability to influence decisions at the executive level and drive high levels of collaboration across internal and external stakeholders.
  • Multi-modal experience in TL, LTL, Bulk, Rail, and small parcel; Hazmat and Freight Forwarding experience a plus.


Base Pay Range: $180,000–$200,000 annually

Commission Eligible: Yes


About the Company

This organization delivers multimodal transportation and logistics solutions spanning intermodal rail, trucking, warehousing, and managed transportation services across North America, Europe, and Asia-Pacific. Backed by a multibillion-dollar freight network, it holds direct contracts with major Class 1 rail carriers and operates one of the largest independent marketing channels for domestic cabotage of ocean carrier equipment. The company serves industries including chemicals, metals, food and beverage, and packaged freight, and carries Responsible Care® certification reflecting its expertise in safety-sensitive logistics. It combines deep carrier relationships and a broad equipment fleet with AI-powered technology to optimize freight movement and pricing for its customers, while its sustainability initiative uses data-driven insight to reduce costs and environmental impact across the supply chain.



About Caliber

Caliber is a specialized talent agency built by freight professionals, not career recruiters, dedicated exclusively to the freight forwarding and logistics industry. Our mission is simple: to match the best talent in the industry with the best companies in the industry. Because our team comes from within the industry, we understand both the technical demands of the roles we fill and the culture of the companies we represent. As a niche agency, we strive to be recognized among the best in our field while operating as servant leaders within the freight and logistics community.


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