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Senior Underwriter Middle Market Property

Starr Insurance · Chicago, IL · $135,000–$150,000 a year · Full time

Posted Mar 20, 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 time you grew new business with a broker who wasn't sending you submissions before.

What they are checking: Production skill, since the role is meant to help drive growth on the book.

Tell me about an underwriting decision you later regretted. What did you change afterward?

What they are checking: Self-awareness and learning from mistakes, which matters in a high-authority role.

What would you do

A renewal has a large hail loss and the insured wants the same deductible. What do you do?

What they are checking: Using loss experience to adjust terms while explaining the reasoning to the broker.

How do you handle a submission with incomplete information when the broker needs a quick indication?

What they are checking: Balancing speed and diligence, and knowing when to qualify an indication with conditions.

How do you prioritize your submission flow when you get more than you can quote well?

What they are checking: Triage skills that focus effort on accounts that fit appetite and are likely to bind.

About the work

This team runs a $600M nationwide property book. How do you think about your accounts as part of a portfolio that size?

What they are checking: Whether they see how individual decisions affect aggregation, mix and results across a large book.

Walk me through how you decide terms on a risk that falls within your underwriting authority.

What they are checking: Confidence and structure in making independent decisions inside their delegated limits.

For a risk outside your authority, what goes into a strong written referral?

What they are checking: Whether they can make a clear case for leadership approval, which the posting lists as a duty.

How do you evaluate COPE for a large manufacturing location with older construction?

What they are checking: Technical depth on construction, occupancy, protection and exposure for complex property risks.

Which catastrophe models or tools have you used, and how do you interpret their output?

What they are checking: Familiarity with cat modeling and the judgment to question model results.

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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 Middle Market Property team is seeking an experienced Senior Underwriter to join and help drive growth on our $600M nationwide property book. This role is critical to underwriting new and renewal business for middle market property risks. The Senior Underwriter will report to regional leadership and be based in one of our primary regional offices. Location: New York, NY; Chicago, IL; Atlanta, GA; Houston, TX; Dallas/Addison, TX Key Responsibilities: • Solicit and review new and renewal property submissions from diverse 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. • 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. • Prepare and submit required reports to Home Office and management. • Perform additional duties as assigned by management. Qualifications: • Bachelor’s degree in business, finance, insurance, or related field. • Minimum of 5 years of direct property underwriting experience, preferably in 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. Preferred: • Professional designations (CPCU, ARM, etc.) or progress toward completion. Companies is required by law to include a reasonable estimate of the compensation range for this role. The wage range for this role takes into account the wide range of factors that are considered in making compensation decisions including but not limited to skill sets: experience and training: licensure and certifications: and other business and organizational needs. A reasonable estimate of the current range is $135,000-$150,000 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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