Commercial Underwriter Trainee — Hybrid & Growth Path

The Hartford; Chicago (IL); Hybrid; USD 61,000 - 91,000; Full time

Job summary

The Hartford is seeking an Associate Underwriter for the UYTRAN program in Chicago. This 22-week onboarding and risk education program blends on-the-job experience with classroom learning, mentorship, and sales training to develop commercial underwriting skills.

The role supports a hybrid schedule—three days in the office and two days from home—while you build relationships, analyze data, and learn to deliver precise coverage for customers.

Qualifications

• Bachelor’s Degree preferred, or equivalent combination of education, training, and Insurance experience.
• Up to 3 years of Insurance experience preferred.
• Excellent written and interpersonal communication and presentation skills.
• Ability to think analytically about business problems, make recommendations, and propose solutions.
• Resilience and an entrepreneurial spirit.
• Demonstration of solid time, organizational, and desk management skills.
• Goal oriented with a strong desire to deliver outcomes in timely manner.
• Acts with a sense of urgency and is responsive to internal and external customer needs.
• Strong sales skills with the ability to negotiate and sell all messages including with those that may be difficult.
• Challenge the status quo to implement improvement and compete to win.
• A valid driver’s license is required, as use of a company pool car will be necessary for periodic travel.
• Demonstrates satisfactory progress during the Training Program and achieve passing scores on all tests, case studies, and foundational underwriting assessments
• Potential to travel during training may exist

Skills

Customer focus

Data analysis

Critical thinking

Team spirit

Financial mindset

Relationship building

Time management

Sales skills

Urgency responsiveness

Education

Bachelor’s Degree or equivalent

Job description

The Hartford is seeking an Associate Underwriter for the UYTRAN program in Chicago. This 22-week onboarding and risk education program blends on-the-job experience with classroom learning, mentorship, and sales training to develop commercial underwriting skills.

The role supports a hybrid schedule—three days in the office and two days from home—while you build relationships, analyze data, and learn to deliver precise coverage for customers.