Sr. Underwriting Specialist

Built on meritocracy, our unique company culture rewards self-starters and those who are committed to doing what is best for our customers.

Oxford Risk Management Group is seeking a Senior Underwriting Specialist to join our growing team in

The Senior Underwriting Specialist will independently evaluate and underwrite complex Commercial Casualty risks, with an emphasis on Commercial Auto, Commercial General Liability, and Excess Liability. This role requires strong technical expertise, sound underwriting judgment, and the ability to develop well-supported coverage, pricing, and captive program recommendations.

How You Will Contribute:

• Independently underwrites new and renewal Commercial Casualty accounts, with primary emphasis on Commercial Auto, Commercial General Liability, and Excess Liability coverages.

• Evaluates large and complex risks by analyzing operations, exposures, loss experience, financial information, risk-management practices, coverage needs, and proposed program structure.

• Develops well-supported underwriting recommendations regarding risk selection, pricing, coverage terms, limits, deductibles or retentions, captive participation, attachment points, exclusions, and other conditions of coverage.

• Reviews and interprets Commercial Auto, Commercial General Liability, and Excess Liability policies, including ISO forms and endorsements, non-ISO forms, proprietary coverage forms, and manuscript endorsements.

• Applies a strong understanding of coverage mechanics to evaluate how definitions, exclusions, conditions, limits, aggregates, defense provisions, underlying insurance requirements, and endorsements interact within and across policy layers. (cut?)

• Identifies coverage gaps, inconsistencies, unintended coverage grants, and conflicts between quoted terms, underlying policies, excess coverage, and issued policy documents.

• Applies knowledge of admitted, non-admitted, and surplus lines insurance markets, including the regulatory, filing, documentation, and procedural requirements associated with each placement structure.

• Develops and maintains strong knowledge of the trucking and transportation industry, including fleet operations, vehicle ownership and leasing arrangements, driver management, commodities hauled, operating radius, federal and state filings, safety performance, and emerging industry trends.

• Reviews motor-carrier information and transportation-specific risk indicators, including vehicle and driver schedules, operating authority, inspection and violation history, crash data, safety measurements, loss trends, and risk-control practices.

• Analyzes detailed loss runs and claims information to identify loss frequency, severity, development, open-claim concerns, litigation trends, and patterns that may affect risk selection, pricing, coverage, or program structure.

Licenses & Certifications:

• Property and Casualty insurance license and/or a recognized industry designation such as CPCU, AU, ARM, or CIC. (preferred)

Skills & Experience to be Successful:

• Bachelor’s degree and a minimum of seven years of progressively responsible Commercial Property and Casualty underwriting experience; an equivalent combination of education and relevant industry experience may be considered.

• Significant underwriting experience with Commercial Auto, Commercial General Liability, and Excess Liability coverages, including experience evaluating complex casualty risks.

• Strong technical knowledge of commercial insurance coverage forms, policy construction, and coverage mechanics, including ISO forms and endorsements, non-ISO forms, and manuscript endorsements.

• Demonstrated experience analyzing exposure information, loss runs, claims history, pricing considerations, and other underwriting data to develop well-supported risk-selection and coverage recommendations.

• Working knowledge of admitted, non-admitted, and surplus lines markets and the general requirements associated with each placement structure.

• Experience reviewing and evaluating policy terms, limits, deductibles or retentions, attachment points, exclusions, underlying insurance, defense provisions, and other material coverage conditions.

• Demonstrated ability to independently manage complex accounts, exercise sound underwriting judgment, and clearly document and communicate underwriting recommendations.

• Strong written, verbal, analytical, organizational, and interpersonal communication skills.

• Advanced proficiency in Microsoft Office, particularly Excel, with the ability to organize and analyze large and complex data sets.

• Underwriting experience within the trucking and transportation industry. (preferred)

• Experience underwriting captive insurance programs or other alternative-risk structures. (preferred)

• Experience working with actuaries to evaluate loss development, actuarial assumptions, projected losses, and account-specific loss selections. (preferred)

• Experience underwriting accounts involving multiple coverage lines, insurance layers, entities, jurisdictions, or complex program structures. (preferred)

Pay Range

$140,000 - $145,000 Annual

The pay range provided above is made in good faith and based on our lowest and highest annual salary or hourly rate paid for the role and takes into account years of experience required, geography, and/or budget for the role.

Teammate Benefits & Total Well-Being

We go beyond standard benefits, focusing on the total well-being of our teammates, including:

• Health Benefits: Medical/Rx, Dental, Vision, Life Insurance, Disability Insurance  
• Financial Benefits: ESPP; 401k; Student Loan Assistance; Tuition Reimbursement 
• Mental Health & Wellness: Free Mental Health & Enhanced Advocacy Services
• Beyond Benefits: Paid Time Off, Holidays, Preferred Partner Discounts and more. 

Not reflective of all benefits. Enrollment waiting periods or eligibility criteria may apply to certain benefits. Benefit details and offerings may vary for subsidiary entities or in specific geographic locations. 

Recruiting Vendor Disclosure Statement

Brown & Brown does not accept unsolicited resumes from external recruiters, recruitment vendors or employment agencies ("Recruiting Vendors"). Recruiting Vendors must have a valid written agreement and received prior written authorization from an authorized Brown & Brown representative before submitting candidates for any publicly posted role. Any unsolicited resumes submitted to Brown & Brown or its employees become the property of Brown & Brown, and no fees will be paid for such submissions. Additional information regarding this policy can be found on our careers page.

The Power To Be Yourself  

As an Equal Opportunity Employer, we are committed to fostering an inclusive environment comprised of people from all backgrounds, with a variety of experiences and perspectives, guided by our Diversity, Inclusion & Belonging (DIB) motto, “The Power to Be Yourself”.