Sompo
Overview
Underwriter Trainee, Primary Retail Casualty — Chicago, IL. Sompo offers an 18-month Trainee Program beginning in July 2026 designed to equip you with the essential business and technical skills needed to build a successful career in insurance. As an Underwriting Trainee you will work alongside experienced underwriters to gain in-depth knowledge of our business units and underwriting philosophy through on-the-job learning and workplace mentoring. Trainees work directly on their products’ accounts, building relationships and identifying customers’ needs. The curriculum includes training in negotiation, risk analysis and relationship management. The Trainee Program serves as a launchpad for career advancement. Responsibilities
On-the-job learning: assist Underwriters with exposure analysis and operational analysis of insureds, compile competitor analyses from public databases, develop renewal lists with Underwriting Assistants, contact brokers for submissions, and accompany underwriters during internal meetings and occasional external marketing calls. Activities, Learning and Development: participate in directed self-study and professional designation courses; Sompo covers fees and textbooks, offers time off for exams, and provides additional compensation for successful course completion. Career development: receive professional development training on topics aligned with the respective business unit. Qualifications
Bachelor’s degree Graduation date between May 2025 and May 2026 Genuine interest in developing a career in the insurance industry Ability to articulate ideas clearly through written and verbal communication Solution-oriented mindset and data analytical skills Ability to work independently and collaborate with others Adaptability to new challenges and ability to thrive in a fast-paced environment Demonstrates integrity and reliability in fulfilling roles and responsibilities Detail-oriented, organized, and tech-savvy (Microsoft Excel, Word, PowerPoint) Local to the desired office location or able to arrange housing and transportation for in-office work during the Trainee Program Eligible candidates must be at least 18 years old and authorized to work in the United States without restriction Salary and Benefits
Salary Range: $70,000 – $77,500. Actual compensation depends on factors including cost of living, qualifications, skills, competencies, and experience. Two medical plans to choose from (Traditional PPO and a Consumer Driven Health Plan with an HSA) Pharmacy benefits with mail order options Dental benefits including orthodontia for adults and children Vision benefits Flexible Spending Accounts Company-paid Life & AD&D benefits with option to purchase additional coverage Company-paid Disability benefits with salary continuation 401(k) with employer contributions Paid time off and company holidays Parental leave benefits and adoption assistance Employee Assistance Program Tax-Free Commuter Benefit Tuition Reimbursement & Professional Qualification benefits Equal Opportunity
Sompo International is an equal opportunity employer. We value inclusion and diversity and do not discriminate based on race, color, religion, sex orientation, national origin, or age.
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Underwriter Trainee, Primary Retail Casualty — Chicago, IL. Sompo offers an 18-month Trainee Program beginning in July 2026 designed to equip you with the essential business and technical skills needed to build a successful career in insurance. As an Underwriting Trainee you will work alongside experienced underwriters to gain in-depth knowledge of our business units and underwriting philosophy through on-the-job learning and workplace mentoring. Trainees work directly on their products’ accounts, building relationships and identifying customers’ needs. The curriculum includes training in negotiation, risk analysis and relationship management. The Trainee Program serves as a launchpad for career advancement. Responsibilities
On-the-job learning: assist Underwriters with exposure analysis and operational analysis of insureds, compile competitor analyses from public databases, develop renewal lists with Underwriting Assistants, contact brokers for submissions, and accompany underwriters during internal meetings and occasional external marketing calls. Activities, Learning and Development: participate in directed self-study and professional designation courses; Sompo covers fees and textbooks, offers time off for exams, and provides additional compensation for successful course completion. Career development: receive professional development training on topics aligned with the respective business unit. Qualifications
Bachelor’s degree Graduation date between May 2025 and May 2026 Genuine interest in developing a career in the insurance industry Ability to articulate ideas clearly through written and verbal communication Solution-oriented mindset and data analytical skills Ability to work independently and collaborate with others Adaptability to new challenges and ability to thrive in a fast-paced environment Demonstrates integrity and reliability in fulfilling roles and responsibilities Detail-oriented, organized, and tech-savvy (Microsoft Excel, Word, PowerPoint) Local to the desired office location or able to arrange housing and transportation for in-office work during the Trainee Program Eligible candidates must be at least 18 years old and authorized to work in the United States without restriction Salary and Benefits
Salary Range: $70,000 – $77,500. Actual compensation depends on factors including cost of living, qualifications, skills, competencies, and experience. Two medical plans to choose from (Traditional PPO and a Consumer Driven Health Plan with an HSA) Pharmacy benefits with mail order options Dental benefits including orthodontia for adults and children Vision benefits Flexible Spending Accounts Company-paid Life & AD&D benefits with option to purchase additional coverage Company-paid Disability benefits with salary continuation 401(k) with employer contributions Paid time off and company holidays Parental leave benefits and adoption assistance Employee Assistance Program Tax-Free Commuter Benefit Tuition Reimbursement & Professional Qualification benefits Equal Opportunity
Sompo International is an equal opportunity employer. We value inclusion and diversity and do not discriminate based on race, color, religion, sex orientation, national origin, or age.
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