Associate Captive Executive

Ryan Specialty•Chicago, IL

1d•$128,370 - $160,000

About The Position

Ryan Alternative Risk is looking for an Associate Captive Executive to take on real ownership of our group captive insurance programs — not just support them. Working alongside a Captive Executive, you'll manage day-to-day program operations, own key client and broker relationships, and help shape the strategic direction of the captives you're assigned to. You'll be the person clients and brokers turn to for answers, the one preparing the board with confidence, and the one making sure the numbers, the renewals, and the relationships all hold together. This role is built for someone ready to grow quickly into full captive leadership — with a clear, visible path to Captive Executive. If you have a solid foundation in commercial insurance, thrive on ownership rather than oversight, and want to build a career in a fast-growing niche of the industry, this is your next step.

Requirements

Bachelor's degree in Business, Insurance, Risk Management, or a related field.
3–5 years in commercial insurance, with a focus on underwriting, risk management, or captives.
Experience supporting or partnering with senior leadership and managing client relationships preferred.
Solid grounding in Property & Casualty insurance, particularly Workers' Compensation, Commercial Automobile, and General Liability.
Familiarity with group captive structures and operations is highly desirable.
Strong organizational skills and the ability to manage multiple priorities in a fast-paced, dynamic environment.
Excellent written and verbal communication skills, including preparing polished documentation and presenting complex information to senior leaders.
Proficiency in Microsoft Office (Excel, PowerPoint, Word); experience with financial or reporting software is a plus.
Strong attention to detail and a proactive approach to problem-solving and process improvement.

Nice To Haves

CPCU or ARM designation is a plus.

Responsibilities

Lead business development efforts for assigned captives, executing the strategy set by Captive leadership and identifying opportunities to expand relationships.
Own the development of new business and renewal proposals, working directly with brokers and clients to explain program mechanics and resolve questions.
Drive client stewardship activities, building strong, lasting relationships with brokers and clients and delivering a consistently high standard of service.
Partner with the Captive Executive on the strategic direction of each captive program, contributing directly to key decisions and ensuring alignment with organizational goals.
Co-lead board preparation, including building board books, financial reports, and strategic updates that give directors a clear, confident view of program performance.
Engage directly with clients, brokers, and service providers to advance business development and keep program activities executing smoothly.
Manage day-to-day operations for assigned captives — renewals, premium collection, and claims oversight — end to end.
Prepare proposals, renewals, actuarial reports, and financial statements to a standard of accuracy and polish that's ready for client and board review.
Track and forecast premiums, expenses, and budget performance, flagging risks early and keeping the captive on solid financial footing.
Monitor risk management strategy alongside the Captive Executive, assessing program performance and surfacing opportunities to improve results.
Compile and interpret reporting on risk exposures, loss ratios, and other key metrics for internal stakeholders and the Board of Directors.
Coordinate closely with underwriting, claims, and compliance teams to keep every part of the captive program running seamlessly.
Mentor junior team members and help build a strong, collaborative team culture.
Pursue ongoing training to deepen captive insurance expertise and prepare for expanded responsibility.