Senior Director Underwriting

The Senior Director Underwriting 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

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:

• Strategic thinking and decision-making


• Highly motivated and take initiative


• Commercial acumen


• Innovation in risk solutions


• Client-centric mindset


• Collaboration and influence

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.