Underwriter Trainee Jobs in Springfield, MA (NOW HIRING)

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UPDATED 5/19/2026: Clinton, NY office has been added as a location

This position is responsible for the successful program management of assigned Captive programs. The Captives Underwriter will develop and maintain effective relationships with internal and external partners to foster positive program results.

You will have responsibility for underwriting workers compensation, general liability and commercial auto for Captive programs. The Captives Underwriter's major purpose is to profitably grow their assigned Captive Programs and achieve underwriting excellence.

The Captives Underwriter does not have any direct reports but is the client manager and is responsible for influencing internal and external partners to achieve positive program results.

Attendance at Board meetings and client seminars with some international travel possible (10% - 25%).

Responsibilities:

Technical Underwriting and Risk Selection

• Rigorously analyzes underwriting information in assessing risk for each account.

• Is creative in the use of underwriting tools and techniques to write profitable business while maintaining disciplined adherence to underwriting standards.

• Is able to communicate rationale for underwriting decisions.

• Exhibits a commitment to finding ways to write business without sacrificing quality.

Program Management

• Participation in all aspects of program management such as actuarial pricing, claim or TPA oversight, reinsurance accounting and collateral management.

• Possesses a deep understanding of the business.

• Demonstrated responsiveness and dedication to customers and follow through on service commitments

• Manage program to achieve underwriting excellence, pricing adequacy and targeted ROE's.

Production Underwriting and Sales

• Exhibits a commitment to finding ways to write profitable new business.

• Takes ownership and accountability for growth of assigned Captive Programs.

• Leverages relationships to drive new business and renewal retention opportunities.

Relationship and Team skills

• Demonstrates excellent working relationships with all internal business associates leading to a high level of customer satisfaction.

• Builds strong relationships with Captive customers and Captive Managers.

• Closely manages results and implements specific actions to address shortfalls.

Qualifications:

• Bachelor's Degree preferred, or equivalent combination of education, training and experience

• 5 + years of Auto Liability, Workers' Compensation, and General Liability underwriting experience; loss sensitive underwriting experience preferred.

• Construction underwriting experience desirable

• Experience with Captive insurance programs is desirable

• Strong Excel and Math skills

• Strong loss responsive or captive program and pricing knowledge

• Strong coverage knowledge

• Superior relationship building skills including influencing and negotiation skills

• Robust problem solving and critical thinking skills

• Outstanding at providing Customer Service

• Ability to travel approximately 10% - 25%

***Job title level will be determined after careful consideration of the selected candidate's qualifications***

Location:

This role will have a Hybrid Work arrangement, with the expectation of working in one of the listed office locations three days a week (Tuesday through Thursday).

Compensation

The listed annualized base pay range is primarily based on analysis of similar positions in the external market. Actual base pay could vary and may be above or below the listed range based on factors including but not limited to performance, proficiency and demonstration of competencies required for the role. The base pay is just one component of The Hartford's total compensation package for employees. Other rewards may include short-term or annual bonuses, long-term incentives, and on-the-spot recognition. The annualized base pay range for this role is:

The posted salary range reflects our ability to hire at different position titles and levels depending on background and experience.

Equal Opportunity Employer/Sex/Race/Color/Veterans/Disability/Sexual Orientation/Gender Identity or Expression/Religion/Age

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