Ryan Specialty
Associate Captive Executive
Chicago - Illinois - Wacker · Full-time
Sponsorship not specified$128k-$160kDetected 73 days ago
Business DevelopmentExcelLeadershipCommunicationCollaborationProblem SolvingPublic SpeakingOrganizational SkillsMicrosoft OfficeActuarial ScienceUnderwritingProperty & Casualty
Stay score
odds of building a lasting career here
54Sponsors, lottery-bound
Cap-exempt (no lottery)0
Sponsors this role80
Entry-level history0
PERM / green-card track0
Lottery odds (Level III)83
Fits your clock70
Sponsors, but it's cap-subject — you still face the weighted lottery (~45% per draw at Level III). Good if you win; have a cap-exempt backup on your list.
Lottery odds assume a STEM candidate.
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About the role
- 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.
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.
- Strategic Support & Leadership Collaboration
- 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.
- Manage day-to-day operations for assigned captives - renewals, premium collection, and claims oversight - end to end.
Requirements
- Familiarity with group captive structures and operations is highly desirable.
- Proficiency in Microsoft Office (Excel, PowerPoint, Word)
Nice to have
- Engage directly with clients, brokers, and service providers to advance business development and keep program activities executing smoothly.
- 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.
- Pursue ongoing training to deepen captive insurance expertise and prepare for expanded responsibility.
- 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.
Skills
- 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.
Compensation
- Industry Knowledge: Solid grounding in Property & Casualty insurance, particularly Workers' Compensation, Commercial Automobile, and General Liability.
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