Senior Captive Insurance Underwriter (Commercial Auto)

Job Title: Senior Captive Insurance Underwriter (Commercial Auto)

Company: Captives.Insure

Location: Remote - Company Headquarters: Knoxville TN

Job Type: Full-time, Senior Level

Job Summary:

The Senior Captive Insurance Underwriter (Commercial Auto) is a non-production, technical underwriting role responsible for complex commercial auto captive insurance programs for high-performing middle market and large accounts (gross written premiums exceeding $500,000). Commercial auto is the primary line of focus, supported by broader property and casualty competence across related coverages. This role requires meticulous fleet and exposure analysis, severity-aware risk assessment, and the ability to structure profitable captive solutions for large and complex auto risks. The successful candidate will collaborate closely with brokers, referral underwriters, captive managers, and internal stakeholders to ensure optimal risk management outcomes and client satisfaction.

Key Responsibilities:

• Evaluate complex commercial auto captive submissions, with thorough analysis of fleet exposures (size, composition, radius of operation, commodity hauled, and DOT/FMCSA authority), loss histories, financial statements, actuarial reports, and related documentation, consistent with our delegated underwriting authority and program obligations.
• Assess auto-specific risk quality through MVR review, CSA/BASIC scores, telematics/dashcam data, and evaluation of fleet safety and loss-control programs.
• Develop and structure customized captive solutions—including large-deductible, SIR, and retro/loss-rated program designs—with appropriate pricing, terms, conditions, attachment points, and compliance with company underwriting guidelines.
• Apply disciplined judgment to severity exposure, accounting for nuclear-verdict/social-inflation trends, umbrella/excess attachment discipline, and accumulation exposure for large fleets.
• Manage an assigned book of business with gross written premiums exceeding $500K per account; responsible for achieving profitability targets (e.g., loss ratio) and renewal retention objectives.
• Collaborate closely with brokers, captive managers, and clients to clearly communicate underwriting decisions, negotiate terms effectively, and maintain strong professional relationships.
• Prepare comprehensive underwriting reports outlining risk assessments, pricing rationale, coverage recommendations, and profitability projections.
• Act as a technical expert within the underwriting team, providing guidance and mentorship to junior underwriters and support staff.
• Participate in client meetings, presentations, industry conferences, and workshops to promote company expertise in captive insurance solutions.

Required Qualifications:

• Minimum of 5 years of progressive property and casualty underwriting experience, with demonstrated expertise managing complex accounts with gross written premiums of $500K–$10M.
• Demonstrated commercial auto/transportation underwriting experience across coverages such as owned, non-owned, hired, garage, and lessor's contingent auto.
• Familiarity with AM Best-rated fronting carriers and reinsurance arrangements.
• Extensive knowledge of captive insurance structures including single-parent captives, group captives, reinsurance arrangements, and alternative risk transfer mechanisms.
• Strong analytical skills with proven ability to interpret complex financial data, actuarial analyses, loss histories, and fleet exposure information.
• Exceptional negotiation skills with the ability to clearly articulate underwriting rationale to brokers and clients.
• Proficiency in Microsoft Office Suite (Excel, Word) and familiarity with underwriting software systems.

Preferred Qualifications:

• CPCU designation, ideally paired with a transportation-specific credential.
• Actuarial or loss-development fluency for fleet experience rating.
• Prior experience underwriting trucking/transportation programs within an MGA or program environment.
• Associate in Captive Insurance (ACI) designation or equivalent.

Expected Working Conditions:

• Location: Fully remote; open to qualified candidates nationwide within the continental U.S.
• Office Environment: Home office setting with standard business hours; flexibility is required to accommodate the demands of the role and multiple time zones.
• Travel: Occasional travel required for client/broker meetings, carrier touchpoints, or industry events (up to 15%).
• Work Hours: While the standard workweek is 40 hours, the role can occasionally require additional hours, including evenings and weekends, to meet deadlines and manage urgent issues.
• Client Interaction: High level of broker interaction, requiring excellent interpersonal skills and the ability to manage relationships effectively.
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Compensation and Benefits:

Compensation for this role has been set based on the individual’s relevant experience, skills for the role, and location.  At Captives.Insure, you’ll be supported with resources, benefits, and work-life balance so you can thrive in ways that matter to you.

• Minimum $175,000 per annum.
• 100% company paid medical, dental and vision benefits (both employee and family).
• The company does not have any limits on Paid Time Off, we just ask for reasonable advance notice.
• 401k with 3% employer match.
• Company profit sharing.
• Relocation assistance if required

Headquartered in Tennessee, Captives Insure ("C.I.") is an award-winning captive insurance consulting and underwriting firm. Recipients of multiple industry awards, C.I. works with sophisticated global captive managers and brokers to provide captive insurance solutions designed to maximize control and premium retention for high-performing businesses around the world. Highly respected within the industry, our distribution network includes independent third-party captive managers and well over half of the top 100 brokerage agencies in the US (as measured by Business Insurance Magazine).

We believe in a diverse and inclusive workforce and are proud to be an equal opportunity employer and welcome applications regardless of ethnicity or cultural background, age, gender, nationality, religion, disability or sexual orientation. We encourage you to bring your whole self to work, no matter where you are from, what you look like, who you love or what you believe in.