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Executive Underwriter & Team Lead, Small Business Casualty

Confidential

USA, Richmond, Virginia, Virginia Hybrid permanent

Posted: January 30, 2026

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Quick Summary

We are seeking an experienced underwriter to join our Small Business Casualty team, underwriting a variety of general and trade contractors as well as premises driven accounts including real estate, hospitality, and habitational businesses.

Job Description

We’re looking for an Executive Underwriter & Team Lead, Small Business Casualty

Hamilton Select is looking for an experienced underwriter to join our Small Business Casualty team, underwriting a variety of general and trade contractors as well as premises driven accounts including real estate, hospitality, and habitational businesses.  This position will report to the VP, Small Business, Casualty Division Manager; this position will also have several direct reports.

 

We prefer to base the position in Richmond, VA, but we will consider a remote working location for appropriately qualified candidates. 

 

Hamilton Select, a subsidiary of Hamilton Insurance Group, LTD, is an Excess and Surplus Lines (E&S) insurance company headquartered in Richmond, Virginia. Hamilton Select writes hard-to-place and distressed accounts in the small and middle-market space through an appointed wholesale broker network.

What you will do

Underwrite challenging and complex new and renewal submissions within underwriting guidelines and make sound risk decisions that balance our growth and profitability targets.

Active involvement in the marketing of Hamilton and our Small Business Casualty Division while working to establish relationships with wholesale brokers

Drive the general use of technology to produce superior profit and establish an ease-of-doing business reputation with our appointed trading partners

Negotiate terms and conditions consistent with our coverage-focused underwriting strategies

Market our insurance products through various communications channels and occasional business travel

Establish and monitor key performance metrics to ensure best-in-class operating effectiveness

Establish and maintain underwriting standards and discipline to ensure the delivery of profitable results

Monitor key metrics and ratios with an eye on efficiency and profitability.

Train and mentor new underwriters

Ensures team compliance with applicable letters of underwriting authority and compliance with applicable state rules and regulations

Participate in special projects and corporate initiatives

 

Conduct Standards

 

You must act with integrity

You must act with due skill, care and diligence

You must be open and cooperative with the FCA, the PRA and other regulators

You must pay due regard to the interests of customers and treat them fairly

You must observe proper standards of market conduct

You must act to deliver good outcomes for retail customers

 

 

What you require for the role

 

An established underwriter with underwriting experience handling Small Business Casualty lines

Strong technical knowledge of Small Business Casualty exposures and coverage, with the ability to further develop themselves and mentor the wider team as the book grows

Management experience or an interest to develop/build management skills

Existing relationships within the wholesale broker community and the demonstrated ability to build effective relationships

Strong internal and external communication skills, both verbal and written

Keen attention to detail, sharp analytical competence, and advanced problem-solving skills

Bachelor’s degree preferred, but not required, with commensurate work experience considered

Acute focus on customer service to meet and exceed our best-in-class service

CPCU designation or other industry coursework preferred, but not required

Ability to travel from time to time to promote our corporate interests

What you can expect from us

We offer a vibrant, entrepreneurial, and collaborative culture guided by our values: Be Smart, Be Sensible, Be Open and Be More.

We know if we welcome and respect differences, we’ll attract and retain talent that brings a valuable diversity of perspectives and experience. We want all our colleagues to feel that they can bring their whole selves to work at Hamilton and know that they can be part of building a great company.

Hamilton offers a competitive salary with an annual performance-based target bonus and a comprehensive benefits package, to include:

Hybrid working

Matching 401K plan

Medical, dental, vision, life, disability

Generous time off (including parental leave)

Continued support for professional development

Gym subsidy

My day (additional days leave for personal interests/wellness/charity work)

In good company.

At Hamilton, we’re building a global specialty insurance and reinsurance company focused on underwriting expertise, enhanced by data and technology to deliver significant shareholder value.

Headquartered in Bermuda, we operate on a global basis, with over 600 employees and key underwriting operations in London, Bermuda, the US and Dublin.

Join us as we continue to drive Hamilton’s evolution into a diversified specialty insurance and reinsurance company. You’ll be in an environment where our colleagues work collaboratively, share a passion for the service and results we deliver, and know that what we do each day is meaningful – to our customers and our business.

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