Carrier Sales Representative - Chicago
Posted Sep 29, 2026 · We last checked this listing on Oct 6, 2026
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Likely interview questions for this role
Written from this job description, not a generic list. Each one notes what the interviewer is really checking.
About your past
The posting says money motivated. Tell me about something you worked hard for because the reward was worth it.
What they are checking: Whether their drive is real and sustained, which carries them through a demanding sales job.
Tell me about a time you built a relationship with someone who was skeptical of you at first.
What they are checking: Whether they can earn trust with owner-operators and dispatchers who get many broker calls a day.
Tell me about a time you had to multitask under pressure and still keep your details right.
What they are checking: Whether accuracy holds up when volume spikes, since a wrong address or rate costs real money.
What would you do
A load needs to move tomorrow and the carrier wants $400 more than your target. How do you negotiate?
What they are checking: Whether they negotiate using market data and relationship value without damaging a carrier they will need again.
A carrier you rely on is late for the third time this month. What do you do?
What they are checking: Whether they address service problems directly and protect the customer while keeping the network healthy.
You've got ten loads to cover by end of day and you're behind. How do you prioritize?
What they are checking: Whether they triage by pickup time and difficulty, and ask for help before loads fall through.
How would you build relationships with internal sales reps to grow your book of business?
What they are checking: Whether they see internal partners as a source of volume and know how to earn their trust.
About the work
What do you think the carrier side of a brokerage does, and how is it different from the customer side?
What they are checking: Whether they understand they are buying capacity, not selling a service, and what that means day to day.
How would you find and vet a new carrier for a lane you've never covered?
What they are checking: Whether they think about safety, authority, insurance, and reliability, not just the cheapest rate.
How would you use data to decide whether a rate is fair for a lane?
What they are checking: Whether they can make informed buying decisions with data rather than guessing.
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Practice this out loudThe full job description
As published by Echo Global Logistics.
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