Sales Representative BC - Chicago
Posted Sep 23, 2026 · We last checked this listing on Oct 6, 2026
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
Tell me about a time you built a pipeline from nothing, with no warm leads handed to you. Where did your first ten conversations come from?
What they are checking: Whether they can source their own business, since this role depends on prospecting they do themselves.
Tell me about a deal you lost that you thought you had. What did you learn, and what did you change on the next one?
What they are checking: Whether they draw honest lessons from losses, which matters in a job with a lot of rejection.
How do you plan a week in the field so you're seeing enough owners face to face?
What they are checking: Self-management and activity discipline when nobody is watching their calendar day to day.
Tell me about a time a customer you'd already closed sent you a referral. How did you ask for it?
What they are checking: Whether they actively work referrals and networks, which this posting leans on for new business.
Why outside sales rather than an inside role, and what tells you you'll enjoy walking into businesses cold every day?
What they are checking: Honest self-awareness about the grind of field prospecting, which is where early turnover comes from.
What would you do
Chicago's neighborhoods each have their own small business scene. How would you pick where to start and build from there?
What they are checking: Whether they can plan a territory around clusters of owners rather than driving all over the city.
You walk into a busy salon and the owner says she's happy with her current processor. What do you say in the next thirty seconds?
What they are checking: How they handle the most common brush-off without turning pushy or giving up too fast.
An owner is interested but says they need to talk it over with a partner. How do you keep the deal from going cold?
What they are checking: Whether they manage follow-up and second decision makers without losing momentum or pressuring anyone.
About the work
Explain to a small business owner, in plain words, how a card payment gets from the swipe to their bank account and where the fees come in.
What they are checking: Whether they understand payments well enough to answer the fee questions every merchant eventually asks.
How would you explain the difference between flat-rate and interchange-plus pricing to an owner who just wants to know what it will cost?
What they are checking: Whether they can be clear and honest about pricing, which is what builds trust with skeptical owners.
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Practice this out loudThe full job description
As published by Fiserv.