Freight Brokerage Account Executive
Hirewell
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Chicago, IL · Posted November 2, 2026
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About the job
Company Description : Our client is a privately held, Chicago-based freight brokerage backed by experienced logistics executives with a history of building and scaling successful transportation companies.
The company provides transportation solutions across full truckload, including dry van, refrigerated, and flatbed freight, as well as LTL and expedited services. With a growing customer base, established carrier relationships, and a strong technology platform, the organization combines the resources of an established brokerage with the flexibility and opportunity of a growing business.
This is an opportunity to join a company in its early stages of growth, work directly with experienced leadership, and build a profitable book of business without the account restrictions often found at larger brokerages.
The Position
Job Title: Freight Brokerage Account Executive
Job Type : Full-time; On-site
Responsibilities :
Identify, prospect, and secure new business opportunities with middle-market shippers across various industries.
Build and grow a profitable book of business through consistent prospecting, relationship development, and customer retention.
Manage the full cradle-to-grave brokerage process, including quoting, rate negotiations, carrier procurement, and shipment execution.
Develop customized transportation solutions that meet customer needs while maintaining strong service levels and healthy profit margins.
Build relationships with key decision-makers, including Supply Chain Leaders, Transportation Managers, and Logistics Directors.
Maintain an active sales pipeline, track opportunities, and meet established sales activity and gross profit goals.
Collaborate with leadership and internal resources to support account growth and contribute to the company’s continued expansion.
Experience :
3+ years of experience in freight brokerage, transportation sales, or carrier sales within a 3PL environment preferred.
Proven ability to generate new business, develop customer relationships, and grow a profitable book of business.
Cradle-to-grave brokerage experience preferred, but candidates from split-model sales or carrier sales environments will be considered.
Strong understanding of freight transportation, pricing, carrier procurement, and operations across truckload, LTL, or expedited freight.
Strong communication, negotiation, and problem-solving skills with the ability to work independently.
Self-motivated, entrepreneurial, and comfortable working in a fast-paced, performance-driven environment.
Location : Chicago, IL
Compensation Details: This position offers a competitive base salary plus uncapped 30% commission on gross profit above an established monthly threshold. Additional incentives are available for new customer acquisition, along with phantom equity participation. As production grows, brokers can earn dedicated operational support, allowing them to focus more heavily on sales and business development.