Associate Captive Executive

Ryan Specialty, LLC; Chicago (IL); On-site; USD 128,000 - 160,000; Full time

Benefits offered by this job

Paid time off

Parental leave

Mental health services

Job summary

Ryan Specialty is seeking an Associate Captive Executive in Chicago to take full ownership of group captive programs, manage client and broker relationships, and shape strategic direction. You’ll work closely with a Captive Executive to ensure renewals, financials, and program performance stay aligned with goals.

You will drive business development, lead proposals, and provide strategic leadership while overseeing day-to-day captive operations and risk management—ultimately progressing toward

Qualifications

• Bachelor's degree in Business, Insurance, Risk Management or related field.
• 3–5 years in commercial insurance with focus on underwriting, risk management or captives.
• Experience supporting or partnering with senior leadership and managing client relationships.
• Solid grounding in Property & Casualty insurance, including Workers’ Compensation, Commercial Auto, General Liability; familiarity with group captive structures is desirable.
• CPCU or ARM designation is a plus.

Responsibilities

• Lead business development for assigned captives, executing strategy set by Captive leadership and expanding relationships.
• Own development of new business and renewal proposals, explaining program mechanics with brokers and clients.
• Drive client stewardship activities and deliver high-quality service.
• Partner with Captive Executive on strategic direction and co‑lead board preparation with financial reports and updates.
• 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.
• Forecast premiums, expenses and budget performance, flag risks early.
• Monitor risk management strategy and report on risk exposures and loss ratios for stakeholders and the Board.
• Mentor junior team members and collaborate with underwriting, claims, and compliance teams.

Skills

Client relationships

Underwriting

Risk management

Captives

Education

Bachelor's degree in Business, Insurance, Risk Management

Job description

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.

Equal Opportunity Employer

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.

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].