Small Business Underwriter Trainee

Berkley•Glen Allen, VA

About The Position

Berkley Aspire is a n excess & surplus lines insurer of commercial risks unable to find coverage in the standard markets. We are a business unit of WR Berkley, a publicly traded (NYSE “WRB”) global insurer founded in 1967 . Aspire’s offices are in Scottsdale, Cincinnati, Richmond , and Dallas and we have remote employees living and working across the country. Aspire’s lead coverage line is general liability for small - to medium - sized businesses. We also offer property, environmental, and excess liability on a package basis, and endorsements for workplace violence, cyber and other risks. Our service area is all 50 states and the District of Columbia. Our engagement model is different than most – we bypass traditional wholesalers and contract with retail trading partners directly. We are agent - friendly and demonstrate that in meaningful ways: we handle the stamping, affidavit filings, and other behind - the - scenes paperwork ; we cover hard - to - place risks; our underwriters respond quickly to submissions; we do the premium billing; we offer convenient payment plans; and, we pay full - year commissions upon receipt of the first installment payment. We work hard. We promote from within . We take care of each other and go the extra mile for our customers. We innovate. We collaborate. We give back. And more often than not, we win. If you are looking for a company that offers room for advancement, great benefits, and positive vibes, then Aspire may be the place for you! The Small Business Underwriter Trainee role begins in June 2026 as part of a 6-month structured training program designed to equip early - career professionals with the essential business, analytical, and technical skills needed to build a successful caree r in E&S underwriting. Training includes classroom sessions, directed self - study, participation in a corporate program tailored to the E&S segment of WRB Companies, and hands - on learning through immersive exposure to real underwriting activities. Upon succ essful completion of the program, trainees will transition into a Small Business Underwriter role with delegated underwriting authority on an assigned team. The Trainee will support underwriting activities by participating in daily team operations, assisting underwriters with exposure and risk analysis, contacting agents for submissions, and joining external marketing calls. Under supervision, the Trainee will develop working knowledge of small business underwriting, E&S market dynamics, workflow processes, pricing tools, and systems. Decision-making authority will expand as competency is demonstrated, ultimately preparing them for transition to a full underwriting role.

Requirements

Bachelor’s degree in Finance, Risk Management, Business, or related field
Graduation date near May 2026.
Strong analytical and problem - solving abilities.
Effective verbal and written communication skills.
Customer - oriented mindset with sense of urgency.
Ability to work independently and collaboratively
Adaptability, professionalism, and strong attention to detail.

Responsibilities

Participate in the June 2026 cohort of the 6 month underwriting training program.
Complete directed self-study and corporate E&S training modules.
Immerse in daily team underwriting activities.
Assist underwriters with exposure and risk analysis of insureds.
Contact agents for submissions and supplemental information.
Participate in external marketing calls with underwriters.
Review and help assess new business submissions.
Support accurate pricing by learning underwriting tools and rating methodologies.
Prepare draft issuance instructions and file documentation.
Reinforce Aspire’s ease-of-doing-business service standards.
Pursue continued education and development opportunities.
Operate within delegated underwriting authority as granted