Senior Underwriter-Retail Middle Market Property
Posted Sep 24, 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 retail broker relationship you built that became a steady source of new business.
What they are checking: Whether they can grow submission flow from diverse retail production sources, as the posting expects.
Tell me about a complex property risk you wrote and the judgment calls you made.
What they are checking: Depth of experience and sound underwriting judgment on complex middle market accounts.
Tell me about a time you declined a risk a broker really wanted placed. How did you keep the relationship?
What they are checking: Whether they can say no clearly while preserving future business with the broker.
What would you do
How do you handle a statement of values that looks understated compared with replacement cost?
What they are checking: Insurance-to-value discipline, which protects premium adequacy and avoids coinsurance disputes later.
A broker pushes back hard on your quote and says a competitor is lower. How do you respond?
What they are checking: Negotiation skill and the ability to defend terms with reasons rather than chasing price.
This is a growing platform. What would you do to help build the portfolio beyond writing your own accounts?
What they are checking: Ownership mindset and willingness to contribute to a team that is still being built.
About the work
Walk me through how you analyze a middle market property submission from a retail broker. What do you check first?
What they are checking: A structured review of values, COPE and loss history before any pricing discussion begins.
What additional information do you most often request, and how do you ask without slowing the broker down?
What they are checking: Whether they know what gaps matter and can get answers while keeping the broker engaged.
How do you price a risk with significant flood or wind exposure in your territory?
What they are checking: Understanding of catastrophe loading, deductibles and sublimits on property accounts.
How do loss control reports influence your terms and conditions?
What they are checking: Whether they use engineering findings to shape recommendations, warranties or pricing.
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Practice this out loudThe full job description
As published by Starr Insurance.