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Senior Underwriter-Retail Middle Market Property

Starr Insurance · Chicago, IL · $145,000–$200,000 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 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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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 Middle Market Property team is seeking an experienced Senior Underwriter to join our growing platform and play a key role in building and managing a profitable retail property portfolio. This position will be responsible for underwriting new and renewal business, developing strong broker and client relationships, and applying sound underwriting judgment to complex middle market property risks. The Senior Underwriter will report to regional leadership and will be based in one of our primary regional offices Location: New York, NY; Chicago, IL; Atlanta, GA; Dallas/Addison, TX Key Responsibilities: • Solicit, evaluate, and underwrite new and renewal middle market property business from a diverse range of retail production sources. • Analyze submitted documentation in accordance with company underwriting standards and guidelines; request additional information when necessary. • Within assigned underwriting authority, prepare and present quotation terms and conditions to brokers and clients. • Develop and maintain strong relationships with brokers, agents, clients, and internal business partners to drive profitable portfolio growth. • For risks outside authority, create written referrals and submit with recommendations to appropriate approval authority. • Review and approve binding terms/conditions, including endorsements and amendments for new and renewal business. • Prepare insurance details for binders and reinsurance documentation for underwriting assistants; ensure accurate booking and billing. • Set up, review, and approve policy forms and endorsements for all issued policies. • Approve final bound policy terms prior to distribution to brokers/clients, ensuring compliance with underwriting standards. • Maintain comprehensive file documentation as per company procedures. Qualifications: • Bachelor’s degree in business, finance, insurance, or related field. • Minimum of 5 years of direct property underwriting experience, preferably in retail middle market/commercial lines. • Demonstrated ability to analyze complex risks and make sound underwriting decisions. • Strong communication, negotiation, and relationship-building skills. • Proven ability to work collaboratively within a team and with external partners. • Interest in ongoing professional growth and consideration for future management opportunities. • Proficiency in relevant underwriting platforms and Microsoft Office Suite. Salary range $145,000-$200,000 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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