Associate Captive Executive

Ryan Specialty

. Lead business development efforts for assigned captives .

Posted 9/16/2026full-timeChicago • Illinois • United StatesJuniorMid-Level💰 $128,000 - $160,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in business development within the captive insurance sector, focusing on client relationship management, proposal development, and risk management strategies. Proficient in financial reporting and analysis, with strong organizational and communication skills to support senior leadership and mentor team members.

Highest-signal resume keywords

Business DevelopmentCaptive Insurance ExpertiseRisk ManagementFinancial ReportingClient Relationship Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

UnderwritingRisk ManagementProposal DevelopmentFinancial AnalysisActuarial ReportingPremium CollectionClaims OversightBudget Performance TrackingProperty & Casualty InsuranceWorkers' Compensation

Soft Skills

Organizational SkillsAttention to DetailProblem-SolvingCommunication SkillsMentoring

Tools & Technologies

Microsoft OfficeExcelPowerPointWordFinancial Software

Certifications & Qualifications

CPCUARM

Industry Keywords

Captive StructuresCommercial InsuranceGroup CaptivesLoss RatiosRisk Exposures

About the role

Key responsibilities & impact

Lead business development efforts for assigned captives
Identify opportunities to expand broker and client relationships
Develop new business and renewal proposals
Explain program mechanics and resolve broker and client questions
Drive client stewardship activities
Partner with the Captive Executive on strategic direction and key decisions
Co-lead board preparation, including board books, financial reports, and strategic updates
Engage with clients, brokers, and service providers to advance business development and program execution
Manage captive renewals, premium collection, and claims oversight end to end
Prepare proposals, renewals, actuarial reports, and financial statements
Track and forecast premiums, expenses, and budget performance
Monitor risk management strategy and assess program performance
Compile and interpret reporting on risk exposures, loss ratios, and other metrics
Coordinate with underwriting, claims, and compliance teams
Mentor junior team members
Pursue ongoing training to deepen captive insurance expertise

Requirements

What you’ll need

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
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 ability to manage multiple priorities
Excellent written and verbal communication skills
Proficiency in Microsoft Office (Excel, PowerPoint, Word)
Strong attention to detail
Proactive approach to problem-solving and process improvement
CPCU or ARM designation is a plus
Experience supporting or partnering with senior leadership and managing client relationships preferred
Experience with financial or reporting software is a plus

Benefits

Comp & perks

Paid company holidays
Vacation days
Sick days
Personal days
Paid parental leave
Mental health services
Bonuses for full-time roles
Comprehensive benefits package
Reasonable accommodations for individuals with disabilities