Underwriting Manager-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 an underwriter you developed into a stronger performer. What did you do specifically?
What they are checking: Real coaching ability, since the posting puts leading and developing underwriters first.
Which retail brokers do you have strong relationships with, and how would you bring that business here?
What they are checking: Whether they bring established broker and client relationships, which the posting asks for.
Tell me about a time you had to tell your boss your region would miss its plan. How did you handle it?
What they are checking: Accountability and early communication of bad news to leadership.
What would you do
You'd lead one of four regional property teams. How would you spend your first months understanding the team and the book?
What they are checking: Whether they learn people and portfolio before changing direction, which builds trust with a new team.
One of your underwriters is hitting premium goals but their loss ratio is climbing. How do you address it?
What they are checking: Balancing growth and profitability while giving direct feedback to a strong producer.
A major broker asks for a rate concession on a large account with a recent fire loss. What's your call?
What they are checking: Negotiation skill and the discipline to hold pricing tied to loss experience.
About the work
Walk me through how you underwrite a middle-to-large commercial property risk. What are the COPE factors you weigh most?
What they are checking: Technical depth in construction, occupancy, protection and exposure, the foundation of property underwriting.
How do you think about catastrophe exposure and aggregation when your team writes in wind and quake zones?
What they are checking: Whether they manage cat accumulation at the portfolio level, not just account by account.
How do you set underwriting authority levels for team members, and when do you expand them?
What they are checking: Judgment about delegating authority based on demonstrated skill and risk.
What property market conditions are you watching right now, and how do they shape your growth strategy?
What they are checking: Market knowledge and whether they can turn it into a practical plan for the team.
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Practice this out loudThe full job description
As published by Starr Insurance.