Associate Captive Executive: Client & Strategy Lead

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

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