Senior Director, Alternative Risk Underwriter
Fortegra, Jacksonville, FL, United States
Senior Director, Alternative Risk Underwriter
Job Category
: Senior Director
Requisition Number
: SENIO001620
Posted: April 9, 2026
Full-Time
Locations Showing 1 location
Jacksonville, FL 32256, USA
Description The Senior Director, Alternative Risk Underwriter will be responsible for leading the strategy, underwriting performance, and portfolio management of alternative risk solutions, including captive insurance programs and niche specialty products. This role combines technical underwriting expertise, client advisory, and business development to deliver customized risk solutions for complex clients, with a focus on captives and specialty lines.
Qualifications
Bachelor’s degree in Finance, Risk Management, Insurance, or related field (MBA or advanced degree preferred)
15+ years of underwriting experience, with focus on captives, alternative risk, or specialty lines
Demonstrated experience structuring and managing captive programs
Deep knowledge of captive insurance structures, reinsurance, and risk financing mechanisms
Strong financial analysis and underwriting skills
Familiarity with actuarial concepts and regulatory frameworks
Proven leadership and team management experience
Strong negotiation and relationship management skills
Ability to communicate complex concepts to both technical and non-technical audiences
Professional designations such as CPCU, ARe, or ARM preferred
Experience working with global captive domiciles (e.g., Bermuda, Cayman Islands, Vermont) preferred
Established broker and client network within specialty or alternative risk markets preferred
Key Responsibilities
Lead underwriting strategy for alternative risk programs, including captives, structured solutions, and specialty risks
Evaluate complex risk profiles, pricing adequacy, and coverage structures
Oversee portfolio performance, including profitability, loss ratios, and capital efficiency
Establish underwriting guidelines, authority levels, and best practices
Design and structure captive insurance programs (single-parent, group, cell, and micro-captives)
Analyze feasibility studies, pro formas, and financial projections
Partner with actuarial, legal, and regulatory stakeholders on program formation and governance
Advise clients on optimal risk retention, reinsurance strategies, and capital deployment
Serve as senior advisor to clients, brokers, and consultants on alternative risk strategies
Lead negotiations on complex deals and program structures
Build and maintain relationships with key brokers, captive managers, and reinsurers
Identify and develop new business opportunities in specialty and alternative risk markets
Collaborate with distribution teams to expand market presence
Represent the organization at industry events, conferences, and client meetings
Lead and mentor other underwriters
Foster a high-performance, collaborative underwriting culture
Provide technical guidance and referral support for complex risks
Ensure compliance with applicable insurance regulations and captive domicile requirements
Maintain strong governance and documentation standards
Monitor industry trends and regulatory developments impacting alternative risk
Full benefit package including medical, dental, life, vision, company paid short/long term disability, 401(k), tuition assistance and more
Equal Opportunity Employer. This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.
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: Senior Director
Requisition Number
: SENIO001620
Posted: April 9, 2026
Full-Time
Locations Showing 1 location
Jacksonville, FL 32256, USA
Description The Senior Director, Alternative Risk Underwriter will be responsible for leading the strategy, underwriting performance, and portfolio management of alternative risk solutions, including captive insurance programs and niche specialty products. This role combines technical underwriting expertise, client advisory, and business development to deliver customized risk solutions for complex clients, with a focus on captives and specialty lines.
Qualifications
Bachelor’s degree in Finance, Risk Management, Insurance, or related field (MBA or advanced degree preferred)
15+ years of underwriting experience, with focus on captives, alternative risk, or specialty lines
Demonstrated experience structuring and managing captive programs
Deep knowledge of captive insurance structures, reinsurance, and risk financing mechanisms
Strong financial analysis and underwriting skills
Familiarity with actuarial concepts and regulatory frameworks
Proven leadership and team management experience
Strong negotiation and relationship management skills
Ability to communicate complex concepts to both technical and non-technical audiences
Professional designations such as CPCU, ARe, or ARM preferred
Experience working with global captive domiciles (e.g., Bermuda, Cayman Islands, Vermont) preferred
Established broker and client network within specialty or alternative risk markets preferred
Key Responsibilities
Lead underwriting strategy for alternative risk programs, including captives, structured solutions, and specialty risks
Evaluate complex risk profiles, pricing adequacy, and coverage structures
Oversee portfolio performance, including profitability, loss ratios, and capital efficiency
Establish underwriting guidelines, authority levels, and best practices
Design and structure captive insurance programs (single-parent, group, cell, and micro-captives)
Analyze feasibility studies, pro formas, and financial projections
Partner with actuarial, legal, and regulatory stakeholders on program formation and governance
Advise clients on optimal risk retention, reinsurance strategies, and capital deployment
Serve as senior advisor to clients, brokers, and consultants on alternative risk strategies
Lead negotiations on complex deals and program structures
Build and maintain relationships with key brokers, captive managers, and reinsurers
Identify and develop new business opportunities in specialty and alternative risk markets
Collaborate with distribution teams to expand market presence
Represent the organization at industry events, conferences, and client meetings
Lead and mentor other underwriters
Foster a high-performance, collaborative underwriting culture
Provide technical guidance and referral support for complex risks
Ensure compliance with applicable insurance regulations and captive domicile requirements
Maintain strong governance and documentation standards
Monitor industry trends and regulatory developments impacting alternative risk
Full benefit package including medical, dental, life, vision, company paid short/long term disability, 401(k), tuition assistance and more
Equal Opportunity Employer. This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.
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