Associate Captive Executive

RT Specialty, LLC; Chicago, Northern (IL, KY); Hybrid; USD 128,000 - 160,000; Full time

Job summary

Ryan Specialty is seeking an Associate Captive Executive in Chicago, IL to own day-to-day captive program operations and develop key client and broker relationships. You will drive renewals, prepare proposals, and help shape strategic direction with the Captive leadership.

You'll partner with the Captive Executive, co-lead board materials, forecast budgets, and ensure accurate financial reporting for client reviews. A strong background in commercial insurance and client management is essential.

Qualifications

• Bachelor's degree in Business, Insurance, Risk Management, or related field.
• CPCU or ARM designation is a plus.
• 3–5 years in commercial insurance, focusing on underwriting, risk management, or captives.
• Solid knowledge of Property & Casualty insurance (Workers' Comp, Auto, General Liability).

Responsibilities

• Lead client & broker relationship management for assigned captives, executing strategy and expanding relationships.
• Own development of new business and renewal proposals, explaining program mechanics to brokers and clients.
• Co-lead board preparation, including building board books and financial reports for directors.
• Manage day-to-day operations for captives — renewals, premium collection, and claims oversight.
• Prepare proposals, renewals, actuarial reports, and financial statements for client and board review.
• Track and forecast premiums, expenses, and budget performance; flag risks early.

Skills

Relationship management

Business development

Strategic thinking

Communication skills

Organizational skills

Education

Bachelor's degree in Business, Insurance, Risk Management

CPCU or ARM designation

Tools

Microsoft Office

Job description

Associate Captive ExecutiveSkip to main content## This website uses cookies and other tracking technologies to enhance user experience and to analyze performance and traffic on our website. We also share information about your use of our site with our social media, advertising and analytics vendors. If we have detected an opt-out preference signal then it will be honored. Further information is available in our Cookie Policy# Career SiteAssociate Captive Executive page is loaded## Associate Captive ExecutiveApplylocations: Chicago - Illinois - Wackertime type: Full timeposted on: Posted Todayjob requisition id: JR26-5084**Position Summary**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.**What will your job entail?****Key Responsibilities****Client & Broker Relationship Management*** **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.* **Engage directly with** clients, brokers, and service providers to advance business development and keep program activities executing smoothly.**Operational & Administrative Excellence*** **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.**Risk Management & Strategic Reporting*** **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.**Team Collaboration & Development*** **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.**Required Qualifications*** **Education:** Bachelor's degree in Business, Insurance, Risk Management, or a related field. CPCU or ARM designation is a plus.* **Experience:** 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.* **Industry Knowledge:** Solid grounding in Property & Casualty insurance, particularly Workers' Compensation, Commercial Automobile, and General Liability. Familiarity with group captive structures and operations is highly desirable.* **Skills & Competencies:** + 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.Ryan Specialty is an Equal Opportunity Employer. We are committed to building and sustaining a diverse workforce throughout the organization. Our vision is an inclusive and equitable workplace where all employees are valued for and evaluated on their performance and contributions. Differences in race, creed, color, religious beliefs, physical or mental capabilities, gender identity or expression, sexual orientation, and many other characteristics bring together varied perspectives and add value to the service we provide our clients, trading partners, and communities. This policy extends to all aspects of our employment practices, including but not limited to, recruiting, hiring, discipline, firing, promoting, transferring, compensation, benefits, training, leaves of absence, and other terms, conditions, and benefits of employment.# **How We Support Our Teammates**Ryan Specialty seeks to offer our employees a comprehensive and best-in-class benefits package that helps them — and their family members — achieve their physical, financial, and emotional well-being goals. In addition to paid time off for company holidays, vacation, sick and personal days, Ryan offers paid parental leave, mental health services and more.The target salary range for this position is $128,370.00 - $160,000.00 annually.The wage range for this role considers many factors, such as training, transferable skills, work experience, licensure and certification, business needs, and market demands. The pay range is subject to change and may be modified in the future. Full-time roles are eligible for bonuses and benefits. For additional information on Ryan Specialty Total Rewards, visit our website https://benefits.ryansg.com/. We provide individuals with disabilities reasonable accommodations to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment in accordance with applicable law. Please contact us to request an accommodation at [e-mail] *The above is intended to describe this job's general requirements. It is not to be construed as an exhaustive statement of duties, responsibilities, or physical requirements. Nothing in this job description restricts management's right to assign or reassign duties and responsibilities to this job at any time. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.*