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Regional Underwriting Manager Risk Management Casualty

Starr Insurance · Chicago, IL · Full time

Posted Jun 10, 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 developed an underwriter's skills to the point they could take on more authority.

What they are checking: Coaching ability, since the posting emphasizes mentoring and developing talent.

Which Midwest brokers do you have relationships with, and how would you increase submissions from them?

What they are checking: Whether they bring regional broker connections, which the posting says the ideal candidate has.

Tell me about a time you had to tell a big broker no on a key renewal.

What they are checking: Whether they can hold an underwriting line with a major broker and still keep the relationship working.

What would you do

How would you lead and grow a Midwest primary casualty team in your first year?

What they are checking: Whether they have a realistic plan for people, broker relationships and portfolio growth.

One of your underwriters issues a binder with an error that creates coverage the company didn't intend. How do you respond?

What they are checking: How they handle mistakes, protect the company and coach without destroying confidence.

How do you balance team service levels on indications and quotes with careful underwriting?

What they are checking: Leading a team to deliver fast service without sacrificing quality.

About the work

Walk me through how you underwrite a large risk management casualty account with a loss-sensitive program.

What they are checking: Technical depth in loss-sensitive structures like deductibles and retentions common in risk management accounts.

How do you evaluate collateral and credit risk on a large deductible program?

What they are checking: Understanding that deductible programs create credit exposure that must be secured properly.

How do you review loss runs and actuarial projections to price a primary general liability and auto program?

What they are checking: Analytical skill in loss development and pricing for casualty programs.

What casualty trends, like social inflation or nuclear verdicts, are you watching, and how do they affect your strategy?

What they are checking: Market awareness and the ability to turn trends into underwriting action.

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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. We are seeking an accomplished and dynamic Regional Underwriting Manager to lead our Midwest underwriting team. In this role, you will be responsible for expanding, managing, and mentoring a team underwriting a primary casualty portfolio with a strategic focus on risks brokered from the Midwest region. The Regional Underwriting Manager will oversee all aspects of portfolio management, including team leadership, solicitation of submissions, underwriting analysis, and the preparation and issuance of indications, quotations, and binders. The ideal candidate will bring a robust background in commercial casualty underwriting and regional broker relationships, coupled with a proven ability to lead, develop talent, and deliver high-quality service while achieving company objectives. Key Responsibilities: • Lead, manage, and develop a team of underwriters covering General Liability, Liquor Liability, Workers’ Compensation, and Commercial Automobile risks throughout the Midwest. • Solicit, analyze, and underwrite new and renewal business in alignment with corporate and regional goals. • Oversee evaluation and interpretation of data to assess risks and potential exposures, determining appropriate coverage terms and pricing for each policy. • Ensure timely and accurate preparation and issuance of indications, quotations, and binders for both your own accounts and oversight of your team's output. • Track regional pipeline activity, analyze trends, and provide weekly production reports and forecasts to senior management. • Build and maintain strong relationships with retail and wholesale brokers and clients across the Midwest to drive business growth and ensure high levels of customer service. • Collaborate closely with underwriting team members and cross-functional departments to achieve business objectives. • Monitor account and portfolio performance, providing recommendations for improvements or changes as required. • Remain up to date with industry trends, regional regulations, guidelines, and changes to NCCI and ISO policy forms and endorsements impacting the Midwest market. • Represent the company at Midwest marketing and sales meetings, industry events, and broker visits, requiring occasional travel within the region. Qualifications: • Minimum of 8-10 years of experience in commercial casualty underwriting, with at least 2 years in a leadership or management role. • Demonstrated expertise in risk assessment, pricing, and portfolio management within the commercial casualty insurance sector. • Proven ability to lead and develop staff, multi-task, and efficiently prioritize team and individual workflows against multiple deadlines. • Excellent communication, negotiation, and presentation skills, with a strong professional demeanor in both written and verbal interactions. • Established, productive relationships with regional brokers throughout the Midwest. • Proficiency in underwriting software tools, data analysis, and Microsoft Office Suite. 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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