Director, Alternative Risk Underwriter

Fortegra • Jacksonville, FL

4h

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.

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.

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
• 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

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

Benefits

• Full benefit package including medical, dental, life, vision, company paid short/long term disability, 401(k), tuition assistance and more

What This Job Offers

• Job Type: Full-time
• Career Level: Director