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Underwriting Manager-Retail Middle Market Property

Starr Insurance · Chicago, IL · $225,000–$275,000 a year · Full time

Posted Sep 24, 2026 · We last checked this listing on Oct 6, 2026

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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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The full job description

As published by Starr Insurance.

Join Starr, a global leader in commercial insurance with over a century of expertise. We empower our employees to innovate, make impactful decisions, and build lasting client relationships worldwide. At Starr, you'll work in an entrepreneurial culture alongside accessible leaders, leveraging our financial strength and vast industry experience to deliver solutions for our clients, no matter how complex. Grow your career with a rapidly growing company that invests in its people and their ability to drive real progress. The Retail MM Property Team is seeking an Underwriting Manager to lead one of our four regional underwriting teams. This individual will be responsible for leading and developing a team of Underwriters while managing and growing a profitable retail middle market property portfolio. The Underwriting Manager will serve as a subject matter expert in middle-to-large commercial property and will be a key resource for clients, retail brokers, and internal stakeholders. The successful candidate will bring strong technical underwriting expertise, market knowledge, leadership capabilities, and established broker and client relationships. The Underwriting Manager will report directly to the Head of Retail Middle Market Property. Location: New York, NY; Chicago, IL; Atlanta, GA; Dallas/Addison, TX Key Responsibilities • Lead, develop, and expand a team of Property Underwriters, providing coaching, direction, and technical expertise. • Manage and grow a profitable portfolio of retail middle market property business. • Solicit and review new and renewal property submissions from retail brokers. • Serve as a senior point of contact and subject matter expert for clients, brokers, and internal stakeholders • Lead new and renewal strategy discussions and presentations with clients and brokers. • Provide underwriting guidance and support on complex or significant risks within the region. Qualifications: • Bachelor’s degree in business, Finance, Risk Management, Insurance, Accounting, Economics, or related field is preferred. • 7-12+ years of direct property underwriting experience, preferably in retail middle market or commercial lines. • Deep technical knowledge of middle-to-large commercial property underwriting, including risk selection, pricing, coverage, exposure management, and portfolio strategy. • Strong communication, negotiation, and relationship-building skills. • Proven ability to manage and grow a profitable book of business. • Strong communication, negotiation, presentation, and relationship-building skills • Effective decision-making in complex situations. • Strong organizational, analytical, and prioritization skills. Salary ban $225K-$275K Starr is an equal opportunity employer, which means we'll consider all suitably qualified applicants regardless of gender identity or expression, ethnic origin, nationality, religion or beliefs, age, sexual orientation, disability status or any other protected characteristic. We recruit and develop our people based on merit and we're committed to creating an inclusive environment for all employees. We offer first class training and development opportunities to all employees. Our aim is to grow our own talent and bring out the best in people.

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