Outside Sales Representative - Roofing and Siding
Posted Apr 14, 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 your experience selling roofing and siding to contractors. Which brands and product lines do you know best?
What they are checking: Whether they bring real product knowledge and a book of roofers and remodelers they can call on.
Tell me about a time you helped collect a past-due account without losing the customer.
What they are checking: Whether they can have firm money conversations while keeping the relationship intact.
Tell me about a time you passed competitive pricing or market information back to your company. What came of it?
What they are checking: Whether they see themselves as the company's eyes in the market, not just an order taker.
What would you do
A roofing contractor tells you he is happy with his current supplier. What do you say next?
What they are checking: Whether they can find an opening, like delivery speed or service problems, without bashing the competitor.
A shingle delivery is going to be two days late and the crew is scheduled to tear off tomorrow. What do you do?
What they are checking: Whether they solve the problem fast, since a delayed roof means an open house and an angry contractor.
How do you decide where to spend your time between existing accounts and new prospects?
What they are checking: Whether they can grow new business without letting current accounts slip to a competitor.
About the work
How do you find new accounts in Chicagoland when most contractors already have a supplier?
What they are checking: Whether they have a real prospecting approach, such as cold calls, job site visits and following permits.
How do you protect your margins when a big customer keeps pushing for lower prices?
What they are checking: Whether they understand that commission and company profit both depend on margin, not just volume.
How do you keep track of your sales against budget and margin goals during the month?
What they are checking: Whether they manage their own numbers instead of waiting for a manager to tell them how they are doing.
A contractor wants help picking siding for a job. How do you guide that choice?
What they are checking: Whether they can match products to the job and budget, which builds trust over many projects.
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Practice this out loudThe full job description
As published by US LBM.