Underwriting Trainee, Financial Institutions (July 2027 start)

We are seeking an Underwriting Trainee to join our Financial Institutions team based in the Chicago, IL office. Westfield Specialty’s Underwriting Training Program (UTP) is a 2 year program that provides an entry level opportunity for individuals with the drive to become successful members of our underwriting team. While working within the structure of a formalized training program, trainees will learn underwriting practices by participating in formal as well as on-the-job training. Developing a working knowledge of product language, underwriting practices, policies and guidelines. Upon successful completion of the training, underwriting 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.

Trainee Program Objectives

Industry/Practice/Knowledge

• Demonstrates broad knowledge of the business, the marketplace and company goals, objectives and performance measures through the effective delivery of all products and services.

• 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 our company from others.

• Identifies new product opportunities.

Book Management/Pricing Skills

• Manage assigned territory so that items such as renewals, endorsements (if applicable), 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 detail analysis utilizing appropriate information (exposure/rate/financial & loss) to determine account acceptability, taking customer needs into consideration.

Desired 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.

Please note- the salary for this role is 70k. This role is also eligible for discretionary incentive pay.

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