2027 Summer Intern Program- Underwriting Intern, Chicago

Location: Chicago, IL, United States Department: Trainees and Temporary Workers​

The Westfield Specialty Intern Program is a paid, ten-week program that offers students the opportunity to obtain firsthand insight into the insurance business.  Every day you'll learn and develop your skills but you'll also have a clear and supportive path ahead of you. You'll gain the confidence to take on real projects, build your network and learn from senior leaders across our business.  The 2027 Summer Intern Program will run from June 7th to August 13th.

Program Elements Include

Classroom and On The Job Training

Weekly Lunch and Learn Series with Senior Leaders

Formal Mentor Program

Presentations from Major Brokerage Partners

Teambuilding and Social Activities; including Community Service Event

Industry based Group Project

Participants in the Westfield Specialty Summer Intern Program are immersed in the day-to-day operations of a fast-moving, growing insurance company. You will gain valuable, hands-on experience and insurance industry knowledge during the 10-week program. As a summer intern you will work side-by-side with industry leaders on dynamic projects that provide ample opportunity for challenges, learning and achievement.  At Westfield Specialty, we are proud to emphasize the education and development for the future leaders of the insurance industry.

2027 Summer Intern Program Openings

Alpharetta, GA: Underwriting

Berkeley Heights, NJ: Claims, IT, Operations

Chicago, IL:, IT, Underwriting

New York, NY: Actuary, Marketing, Underwriting

For those who excel in the program, we would welcome the opportunity to discuss full-time employment opportunities at Westfield Specialty after graduation as part of our Trainee Program.

As part of our internship program you will receive

Targeted business training designed to help you refine your professional skills and acumen critical to the success of Westfield professionals;

Technical training to deepen your skill level within your chosen discipline; and an understanding of the broader insurance industry;

Access to additional training to compliment your professional development.

Opportunity to expand your professional network with talented insurance professionals

Role Responsibilities

Underwriting Interns will support Westfield Specialty’s underwriting teams while gaining hands-on experience in the insurance industry and developing foundational technical and analytical skills. This role provides direct exposure to underwriting operations, products, and decision-making processes through meaningful project work and day-to-day team collaboration. Interns will be embedded within a specific underwriting team to gain a comprehensive understanding of the business and contribute to ongoing departmental initiatives.

Responsibilities include

Supporting underwriting teams with research, data analysis, and risk assessment activities.

Assist underwriters in evaluating complex or non-standard insurance applications (e.g., cyber, D&O, E&O, marine, or event insurance).

Research and analyze industry-specific risks, emerging trends, and exposures unique to specialty lines.

Help prepare underwriting files, including summaries of risk factors, coverage recommendations, and pricing justifications.

Organize supporting documentation such as loss runs, financial statements, and supplemental forms.

Conduct competitor analysis and benchmark coverage options or pricing.

Compile data to support the development of underwriting strategies and guidelines.

Attend underwriting meetings and shadow underwriters on client calls or risk reviews.

Participate in training sessions on specialty insurance products, underwriting systems, and risk modeling tools.

Stay updated on niche markets, policy forms, and regulatory requirements in specialty insurance.

Desired Qualifications

Currently matriculated students enrolled at a 4 year college or university pursuing either a Bachelors or Masters degree (required)

Strong GPA preferred (Minimum GPA of 3.2 required)

Strong oral and written communication skills

Leadership experience through work or involvement in community service, athletics, clubs, or other activities preferred

Technically adept/digitally savvy

Ability to be onsite in office 4 days a week

This job description describes the general nature and level of work performed in this role. It is not intended to be an exhaustive list of all duties, skills, responsibilities, knowledge, etc. These may be subject to change and additional functions may be assigned as needed by management.

This is a paid internship.  Intern will be paid on an hourly basis at the rate of $25/hour.

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