Underwriting Trainee, Financial Institutions

About the Role

Westfield Specialty Insurance is seeking an Underwriting Trainee to join their Financial Institutions team in the Chicago, IL office. This is a 2-year training program designed for individuals with the drive to become successful underwriters. Trainees will learn underwriting practices through formal and on-the-job training, developing a working knowledge of product language, underwriting practices, policies, and guidelines. Upon successful completion, trainees will continue to work with their team to understand Westfield Specialty’s underwriting process and perform basic underwriting functions in a market-facing or product underwriting role. This role has a July 2027 start date.

Trainee Program Objectives

Industry/Practice/Knowledge

• Demonstrates broad knowledge of the business, the marketplace, and company goals, objectives, and performance measures.
• Links line of business policies and practices to company strategies.
• Demonstrates forms and coverage knowledge and applies them to exposure.
• Compares company coverages to competitors and differentiates the company.
• Identifies new product opportunities.

Book Management/Pricing Skills

• Manages assigned territory, ensuring renewals, endorsements, claim reviews, and related transactions are completed accurately within accepted company timelines.
• Applies standard pricing to exposures.
• Applies individual loss and expense factors, when applicable.

Risk Selection

• Applies underwriting strategies and standards to pre-qualify risk acceptability.
• Performs detailed analysis utilizing appropriate information (exposure/rate/financial & loss) to determine account acceptability, considering customer needs.

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.
• 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.

Salary for this role is $70,000, eligible for discretionary incentive pay.