Freight Sales Representative Chicago

About the role

We are seeking a Freight Sales Representative who thrives in a cradle-to-grave environment — owning the entire freight lifecycle from prospecting and quoting to carrier sourcing, load tracking, and customer billing. The ideal candidate is both a strong closer and an operational problem-solver, able to build long-term relationships with shippers while ensuring exceptional service execution. If you become extremely successful and need more help, we will staff up to support your book of business from an operations and coverage standpoint.

Key Responsibilities

• Possess and develop new business by identifying and pursuing new shipper accounts across OTR and/or drayage segments.
• Conduct outreach via phone, email, and digital channels to generate leads and secure new freight.
• Negotiate pricing and service agreements with customers to ensure competitive and profitable lanes.
• Manage loads from start to finish — quoting, booking, tracking, problem-solving, and closing out invoices.
• Source and vet carriers through internal systems and external tools (RMIS, Carrier411, load boards, etc.) to ensure compliance with company and industry safety and insurance standards.
• Maintain proactive monitoring of shipments, communicate updates, and resolve issues swiftly.
• Build long-term, trust-based relationships with shippers and carriers by serving as the main point of contact for assigned accounts.
• Provide consistent updates on load status, exceptions, and delivery confirmations.
• Collaborate closely with Amnex leadership to develop lane strategies and customer pricing models.
• Contribute to process improvements, automation initiatives, and technology adoption within the brokerage.

Qualifications

• 2+ years of freight brokerage, logistics sales, or transportation account management experience.
• Proven ability to source, close, and manage freight independently in a cradle-to-grave model.
• Strong knowledge of OTR truckload, intermodal, or port drayage operations.
• Excellent negotiation, communication, and relationship-building skills.
• Proficiency with TMS, load boards, and CRM systems (experience with Turvo, DAT, Truckstop, or similar preferred).
• A self-motivated individual with a strong sense of urgency and attention to detail.

Benefits

• Competitive base salary + uncapped commission structure.
• Performance bonuses and incentive programs.
• Opportunities for growth into leadership or key account roles.