Location: Chicago, IL – West Loop (In Office)
Job Type: Full Time
Years of Experience: 2-7 Years

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About Our Client

Our client is a fast-growing freight brokerage operating out of a new West Loop office in Chicago. The company pays significantly above-market commissions — tiered, uncapped, and paid before the customer even settles — with no territory restrictions and no assigned accounts. Producers who come in with a book or a strong prospecting mentality can generate strong first-year income in an environment that rewards individual performance.

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Position Overview

This is a hunting seat. The rep is responsible for prospecting, cold calling, and winning shipper customers entirely through their own outbound activity. There are no assigned accounts and no handed-over books — every relationship you build is yours.

At the start, the role is cradle to grave: you build loads, manage track and trace, and sell. As your book grows, dedicated account support is added. You will onboard and train under the Client Success Manager for roughly the first three to six months before transitioning to the Director of Sales' team once you are consistently producing.

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Key Skills

• Freight brokerage or 3PL sales experience

• Self-sourced book of business built through cold outbound

• Customer-facing selling of freight services directly to shippers

• High-volume cold calling and outbound prospecting discipline

• Domestic truckload, LTL, drayage, or intermodal fluency

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Role Priorities

• Prospect and cold call to win new shipper customers from scratch.

• Build and manage your own book of business through outbound activity.

• Conduct discovery, negotiate rates, and close freight contracts.

• Run cradle-to-grave operations on your own accounts through early tenure.

• Maintain a full pipeline, CRM activity, and consistent production cadence.

• Work closely with the Director of Sales and Client Success Manager as you ramp.

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Who Thrives in This Role

• You built your book yourself. Every account in your pipeline was found, prospected, and closed by you — nothing was handed over, assigned, or inherited.

• You are a phone-first rep. You are comfortable with high-volume cold calling and treat outbound activity as the core of your day.

• You are production-minded. You know how to run your own accounts cradle to grave and aren't looking for heavy operational support on day one.

• You want upside, not a ceiling. You are drawn to uncapped commission structures and a culture that rewards producers at every level.

• You are ready to be in the office. This is a five-day-a-week in-office role in the West Loop, and you are energized by being on a floor of other producers.

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Key Responsibilities

• Prospect and cold call to identify and win new shipper customers through outbound activity.

• Build a self-sourced book of business from scratch with consistent daily prospecting.

• Conduct discovery, manage negotiations, and close freight contracts.

• Run cradle-to-grave operations on your own accounts — build loads, cover carriers, and manage track and trace.

• Maintain CRM activity, pipeline health, and accurate forecasting.

• Develop lasting shipper relationships and grow accounts over time.

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Qualifications

• 2–7 years of freight brokerage, 3PL, or logistics sales experience with a direct customer sales focus.

• Proven track record of self-sourcing a book of business through cold outbound — no inherited or assigned accounts. This is the one requirement the client will not bend on.

• Comfortable with high-volume cold calling and an outbound-heavy sales motion.

• Experience with domestic truckload, LTL, drayage, or intermodal preferred.

• A portable book of business is a strong plus, though not required.

• Based in or willing to relocate to the Chicago metro; must be able to work from the West Loop office five days per week.

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What's Offered

• Competitive base salary plus uncapped commission, tiering up to 35%.

• Commission paid before the customer pays — strong cash flow for producers.

• No territories, no assigned accounts — everything you close is yours.

• High-growth, entrepreneurial brokerage environment with a flat, producer-first culture.

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If you're a self-sourcing freight broker with a proven track record of building your own book from scratch and want to earn more on the same business you're already writing, we'd love to hear from you.