Outside Sale Consultant - Chicago
Posted Oct 1, 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
This is a 100% hunter role. Tell me about a time most of your results came from new accounts you found yourself.
What they are checking: Whether they have actually lived on new business, not on managing accounts someone else built.
Tell me about a time you earned the trust of a busy, skeptical small business owner.
What they are checking: Whether they build credibility through listening and follow-through, which owner-operators respond to more than polish.
Most owners you approach will say no. How do you keep your energy and your numbers up through a day full of rejections?
What they are checking: Resilience under constant rejection, which is the daily reality of a field hunter role.
Walk me through how you'd plan a full day in the field so you're talking to as many restaurant owners as possible.
What they are checking: Whether they treat prospecting as a planned activity with targets rather than hoping to bump into deals.
Why restaurants? What do you know about how a restaurant owner's day actually goes?
What they are checking: Whether they understand the customer's world well enough to time visits and pitches around it.
What would you do
Chicago has distinct neighborhoods with very different restaurant scenes. How would you tailor your approach from one to the next?
What they are checking: Whether they adjust to local context instead of using the same pitch for every restaurant owner.
A restaurant owner says switching POS systems right now is too risky because they can't afford a bad night. How do you respond?
What they are checking: Whether they take switching risk seriously and can lower the owner's fear with a realistic install plan.
An owner asks whether Clover can handle something specific for their kitchen, and you're not sure of the answer. What do you say?
What they are checking: Honesty about product limits, since overpromising to a merchant leads to angry calls and lost accounts.
About the work
What does a restaurant need from a point-of-sale system that a retail store usually doesn't?
What they are checking: Whether they know restaurant workflows like tips, modifiers, table service and kitchen tickets well enough to sound credible.
How would you explain card processing costs to a restaurant owner who runs on thin margins and watches every fee?
What they are checking: Whether they can talk pricing plainly and honestly with an owner who will check the math.
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As published by Fiserv.