Director, Alternative Risk Underwriter

Fortegra•Jacksonville, FL

About The Position

The Director, Alternative Risk Underwriter will be responsible for underwriting, structuring, and managing complex alternative risk solutions, including captive insurance programs, structured risk deals, and specialty coverages. This role requires strong technical underwriting expertise, financial acumen, and the ability to collaborate with clients, brokers, and internal stakeholders to design customized risk financing strategies. Qualifications: Bachelor’s degree in Risk Management, Finance, Insurance, or related field 10+ years of underwriting experience, with exposure to alternative risk, captives, or specialty lines Experience analyzing complex risks and structuring non-traditional insurance solutions Strong understanding of captive insurance structures and alternative risk transfer mechanisms Solid financial and analytical skills, including interpretation of actuarial models and loss projections Knowledge of reinsurance principles and program design Proficiency in underwriting tools, financial modeling, and data analysis Strong communication and presentation skills Ability to build relationships with brokers, clients, and internal stakeholders Effective negotiation and problem-solving capabilities Key Responsibilities: Underwrite complex alternative risk programs, including captives, large deductible programs, and structured solutions Analyze exposures, historical loss data, and financials to assess risk and determine pricing adequacy Develop tailored coverage structures aligned with client risk appetite and objectives Ensure underwriting discipline, compliance with guidelines, and documentation standards Support the design and implementation of captive insurance programs (single-parent, group, and cell structures) Review feasibility studies, actuarial analyses, and financial projections Collaborate with actuarial, legal, tax, and regulatory teams on program structuring and execution Assist in developing reinsurance strategies and risk transfer mechanisms Manage a portfolio of alternative risk accounts, monitoring profitability, retention, and performance metrics Identify trends, emerging risks, and opportunities for portfolio optimization Participate in renewal strategy, pricing adjustments, and program redesign Partner with brokers, consultants, and clients to understand risk management goals and deliver tailored solutions Support negotiations on deal structure, pricing, and terms & conditions Maintain strong relationships to drive retention and new business opportunities The above cited duties and responsibilities describe the general nature and level of work performed by people assigned to the job. They are not intended to be an exhaustive list of all the duties and responsibilities that an incumbent may be expected or asked to perform. Key Competencies: Analytical thinking and attention to detail Commercial awareness and decision-making Innovation and solution-oriented mindset Collaboration and teamwork Time management and ability to manage multiple priorities Additional Information: Full benefit package including medical, dental, life, vision, company paid short/long term disability, 401(k), tuition assistance and more Job Posting Disclaimer: Fortegra has recently been made aware of unauthorized communications regarding career opportunities by individuals not associated with Fortegra or our recruitment team. Fortegra will only contact you from the Fortegra domain address (@fortegra.com). If you receive a message from someone posing as a Fortegra recruiter via text message, WhatsApp, Telegram or other messaging platform, please report it as phishing and block the sender. Fortegra is not accepting unsolicited resumes from search firms for this position.

Requirements

Bachelor’s degree in Risk Management, Finance, Insurance, or related field
10+ years of underwriting experience, with exposure to alternative risk, captives, or specialty lines
Experience analyzing complex risks and structuring non-traditional insurance solutions
Strong understanding of captive insurance structures and alternative risk transfer mechanisms
Solid financial and analytical skills, including interpretation of actuarial models and loss projections
Knowledge of reinsurance principles and program design
Proficiency in underwriting tools, financial modeling, and data analysis
Strong communication and presentation skills
Ability to build relationships with brokers, clients, and internal stakeholders
Effective negotiation and problem-solving capabilities

Responsibilities

Underwrite complex alternative risk programs, including captives, large deductible programs, and structured solutions
Analyze exposures, historical loss data, and financials to assess risk and determine pricing adequacy
Develop tailored coverage structures aligned with client risk appetite and objectives
Ensure underwriting discipline, compliance with guidelines, and documentation standards
Support the design and implementation of captive insurance programs (single-parent, group, and cell structures)
Review feasibility studies, actuarial analyses, and financial projections
Collaborate with actuarial, legal, tax, and regulatory teams on program structuring and execution
Assist in developing reinsurance strategies and risk transfer mechanisms
Manage a portfolio of alternative risk accounts, monitoring profitability, retention, and performance metrics
Identify trends, emerging risks, and opportunities for portfolio optimization
Participate in renewal strategy, pricing adjustments, and program redesign
Partner with brokers, consultants, and clients to understand risk management goals and deliver tailored solutions
Support negotiations on deal structure, pricing, and terms & conditions
Maintain strong relationships to drive retention and new business opportunities