Underwriting Trainee — 2-Year Training Program

Westfield Insurance; Chicago (IL); On-site; USD 63,000 - 77,000; Full time

Benefits offered by this job

Discretionary incentive pay

Job summary

Westfield Insurance in Chicago, IL offers an Underwriting Trainee position within the Financial Institutions team. The Westfield Specialty Underwriting Training Program (UTP) spans two years, combining formal and on-the-job training to build underwriting knowledge and skills.

Successful trainees will work toward understanding Westfield Specialty’s underwriting process and perform basic underwriting functions in market-facing or product underwriting roles after completion.

Qualifications

• Bachelor’s degree required; recent graduates majoring in Finance or Economics are strongly preferred.
• Graduation date must be no later than June 2027.
• Demonstrated interest in financial markets and/or financial institutions.
• Exceptional written and verbal communication skills.
• Strong attention to detail, coupled with initiative and the ability to thrive in a fast-paced team environment.
• Excellent interpersonal skills with the ability to build effective working relationships.
• Proven ability to work both independently and collaboratively.
• Flexibility to adapt to shifting priorities and manage multiple tasks simultaneously.
• Highly motivated with a strong sense of ownership, accountability, and follow-through.

Responsibilities

• Support book management and pricing within assigned territory, ensuring renewals and related transactions are completed accurately.
• Apply standard pricing to exposures and use loss and expense factors where applicable.
• Assist in risk selection by applying underwriting standards and performing detailed analyses of exposure, rate, and financials.

Skills

Financial markets interest

Communication skills

Attention to detail

Interpersonal skills

Team collaboration

Independent work

Education

Bachelor's degree in Finance or Economics

Job description

Westfield Insurance in Chicago, IL offers an Underwriting Trainee position within the Financial Institutions team. The Westfield Specialty Underwriting Training Program (UTP) spans two years, combining formal and on-the-job training to build underwriting knowledge and skills.

Successful trainees will work toward understanding Westfield Specialty’s underwriting process and perform basic underwriting functions in market-facing or product underwriting roles after completion.