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Sales Manager — Drayage Transportation

Chicago, Illinois

Sales Manager
Location: United States
Reports To: Director of Sales
Employment Type: Full-Time
Compensation: $150,000 base salary + bonus potential

About Cargomatic
Cargomatic is transforming the local trucking industry with cutting-edge technology that connects shippers and carriers in real time. Our mission is to bring transparency, efficiency, and reliability to local freight logistics. Backed by leading investors and trusted by some of the world’s largest brands, we are building a smarter supply chain.

At Cargomatic, we value ownership, accountability, collaboration, and continuous improvement. If you thrive in a fast-paced, high-growth environment and enjoy driving revenue growth, we’d love to meet you.

Position Summary
The Sales Manager is responsible for driving revenue growth by developing new business and expanding relationships with existing customers. This role owns the full sales cycle—from prospecting through close—while also contributing to overall go-to-market execution and market expansion.

This is a high-impact, customer-facing role suited for a motivated sales professional with experience in freight, logistics, or transportation who thrives in a fast-paced, performance-driven environment.

Key Responsibilities
Sales Execution & Pipeline Development
· Develop and execute a territory sales plan targeting shippers, importers/exporters, freight brokers, and BCOs
· Build and manage a robust pipeline of drayage and intermodal transportation opportunities
· Own full-cycle sales execution, including prospecting, qualification, negotiation, and closing
· Consistently meet or exceed revenue and activity targets

Customer Relationship Management
· Build and maintain strong, long-term relationships with customers and logistics partners
· Identify customer needs and position solutions that align with service capabilities
· Negotiate rates, contracts, and service agreements in alignment with company pricing strategy
· Ensure a high level of customer satisfaction and retention

Market & Industry Engagement
· Stay informed on port conditions, capacity constraints, pricing trends, and competitive dynamics
· Develop relationships within the logistics ecosystem, including brokers and supply chain partners
· Represent the company at industry events, conferences, and customer meetings

Cross-Functional Collaboration
· Partner closely with operations to ensure service commitments are met
· Collaborate with internal teams to resolve issues and improve customer experience
· Provide market feedback to inform pricing, product, and service strategy

Sales Operations & Reporting
· Maintain accurate pipeline and activity tracking in CRM systems
· Report on sales performance, forecasts, and key metrics
· Identify opportunities to improve sales processes and efficiency

Qualifications
· 3–6 years of sales experience in drayage, intermodal, trucking, or freight logistics
· Proven track record of meeting or exceeding revenue targets
· Strong understanding of freight, supply chain, or transportation markets
· Experience managing full sales cycle from prospecting through close
· Excellent communication, negotiation, and relationship-building skills
· Self-motivated, organized, and comfortable working independently
· Proficiency with CRM systems (Salesforce or similar)

Preferred Experience
· Existing relationships with shippers, freight brokers, or BCOs
· Experience in port or intermodal environments
· Background in high-growth or technology-enabled logistics companies

Why Join Cargomatic?
We offer competitive compensation and a comprehensive benefits package, including:
· Medical, Dental, and Vision insurance
· 401(k) with company match
· Flexible Spending Accounts (FSA)
· Company-paid Life and Disability insurance
· Generous Paid Time Off and company holidays
· Paid Parental Leave
· Employee Assistance Program (EAP)
· Equity participation in a high-growth company
· Career growth opportunities in a rapidly scaling organization
· Collaborative, high-impact team environment

Cargomatic is proud to be an Equal Opportunity Employer. We are committed to creating a diverse and inclusive workplace where all employees feel valued and empowered to succeed.

 

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