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Executive Underwriter, Cyber and E&O Wholesale

Westfield Insurance
Chicago, IL Full Time
POSTED ON 4/5/2026
AVAILABLE BEFORE 5/3/2026
Job Summary

We are seeking an experienced Executive Underwriter to join our Wholesale Cyber Liability and E&O team. Underwriters are responsible for underwriting a complex book of business, employing the methods necessary to meet projected profitability, gross written premium, and expense goals, management and growth of the overall portfolio of business, implementing proper underwriting discipline/guidelines, marketing and servicing of existing and potential clients. This position would be located in Chicago, IL and will report directly into VP, Head of Wholesale Cyber Liability.

Job Responsibilities

  • Growing and managing a portfolio of profitable wholesale business focused on providing Cyber Liability & Technology and Miscellaneous Errors & Omissions coverage.
  • Compliance with underwriting guidelines, systems, and procedures to align with all underwriting and administrative guidelines
  • General underwriting functions including underwriting submission review, pricing analysis, setting of terms and conditions, and quote/binder/invoice authorizations
  • Seek input from Actuarial Department to set process specific accounts when appropriate
  • Liaise with Claims Department on any specific claims activity and overall market claims concerns, which could potentially affect profitability
  • Marketing – attend client/broker meetings, lunches, dinners, and other social outings as applicable. Meet with key brokers regularly to discuss production, service and other topics relative to division operations
  • Stay current with respect to major industry issues and developments
  • Provide specific reports as needed by senior staff

Job Qualifications

  • 4-year college degree required
  • Minimum 5 years underwriting experience; wholesale experience strongly preferred
  • Solid Writing and Communication Skills
  • Excellent organizational skills, and ability to multi-task
  • Ability to work independently in a fast-paced environment
  • Willingness to travel
  • Must be able to think originally, be willing to challenge ideas and be receptive to constructive feedback
  • Ability to be onsite in office 4 days week, where applicable

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.

Equal Opportunity Employer

United States: All applicants receive consideration for employment without regard to race, color, sex, religion, national origin, age, sexual orientation, gender identity, disability, or status as a protected veteran.

United Kingdom: Westfield is committed to equality of opportunity for all staff and applications from individuals are encouraged regardless of age, disability, sex, gender reassignment, sexual orientation, pregnancy and maternity, race, religion or belief and marriage and civil partnerships.

Salary.com Estimation for Executive Underwriter, Cyber and E&O Wholesale in Chicago, IL
$93,798 to $112,649
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