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  1. Home
  2. chevron_right
  3. accounting & finance
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  5. Captive Senior Benefits Underwriter
Ryan Specialty logo

Captive Senior Benefits Underwriter

Not Disclosed•Full-TimeOn-site

location_onMonroe Harbor, 400, East Monroe Street, Jewelers Row, Loop, Chicago, South Chicago Township, Cook County, Illinois, 60603, United States

Apply Now

About the Role

The Captive Senior Underwriter serves as a strategic partner in driving the long-term profitability of Ryan Specialty Benefits. This position is dedicated to underwriting Health coverage for new business, renewals, and endorsements within a captive insurance model. The role requires a deep understanding of complex employee benefits accounts and the ability to navigate the unique dynamics of captive structures.

You will act as a central hub, collaborating closely with Specialty Sales, the Captive Manager, Claims, Operations, Finance, Legal, Risk, and Compliance. Your work ensures that strategic initiatives are met while maintaining rigorous standards for risk assessment and pricing accuracy. This is a role designed for a seasoned professional who thrives on analyzing medical histories and financial data to articulate clear underwriting analyses and suggest corrective actions to sales teams and broker contacts.

Our Culture and Commitment

Ryan Specialty is an Equal Opportunity Employer committed to building and sustaining a diverse workforce. Our vision is an inclusive and equitable workplace where all employees are valued for their performance and contributions. We believe that differences in race, creed, color, religious beliefs, physical or mental capabilities, gender identity or expression, sexual orientation, and other characteristics bring varied perspectives that add value to the service we provide our clients, trading partners, and communities.

This commitment extends to all aspects of our employment practices, including recruiting, hiring, discipline, and promotion. We provide reasonable accommodations to individuals with disabilities to participate in the application process, perform essential job functions, and receive benefits in accordance with applicable law.

Supporting Our Teammates

We strive to offer a comprehensive, best-in-class benefits package designed to help employees and their families achieve their physical, financial, and emotional well-being goals. Beyond standard paid time off for holidays, vacation, sick, and personal days, Ryan offers paid parental leave, mental health services, and more. Full-time roles are eligible for bonuses and benefits, with additional details available on our Total Rewards website.

Application and Interview Process

To apply, please submit your resume and relevant qualifications through our career portal. We are committed to a fair and accessible hiring process. If you require reasonable accommodations to participate in the job application or interview process, please contact us at HR@Ryansg.com.

Our interview process is designed to assess both technical expertise and cultural fit. Candidates can expect to engage in discussions regarding their experience with captive insurance models, complex underwriting scenarios, and their approach to strategic decision-making and team development.

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Skills, education and keywords

Skills: Health Insurance Underwriting, Captive Insurance Models, Underwriting Software, Data Analysis Tools, Risk Assessment, Pricing Methodologies, Regulatory Compliance, Policy Development, Compliance Management, Data Analysis.

Education: Bachelor's degree in Business, Finance, Economics, or related field required; Master's degree can substitute for 5 years of experience (3 years with Master's instead of 8).

Frequently asked questions about Captive Senior Benefits Underwriter at Ryan Specialty

What does a Captive Senior Benefits Underwriter at Ryan Specialty do?expand_more
A Captive Senior Benefits Underwriter at Ryan Specialty is responsible for the following: Execute underwriting for Health coverage focusing on renewals and new business; Analyze and evaluate risks using manual and experience rating techniques; Deliver timely and accurate quotes by calculating premiums based on assessed risks; and Review medical histories and financial data to analyze applicant information.
What are the requirements for this Captive Senior Benefits Underwriter role?expand_more
To qualify for the Captive Senior Benefits Underwriter at Ryan Specialty position, applicants should have: Bachelor's degree in Business, Finance, Economics, or related field; Minimum of 8 years of Health Insurance Underwriting experience or 3 years with a Master's degree; Minimum of 3 years of experience working with captive insurance models; and Proficiency with underwriting software and data analysis tools.
Where is the Captive Senior Benefits Underwriter role at Ryan Specialty located?expand_more
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Work location

Work model: On-site

location_on

Monroe Harbor, 400, East Monroe Street, Jewelers Row, Loop, Chicago, South Chicago Township, Cook County, Illinois, 60603, United States

Chicago, Illinois

Key Responsibilities

  • check_circleExecute underwriting for Health coverage focusing on renewals and new business
  • check_circleAnalyze and evaluate risks using manual and experience rating techniques
  • check_circleDeliver timely and accurate quotes by calculating premiums based on assessed risks
  • check_circleReview medical histories and financial data to analyze applicant information
  • check_circleMeet new business premium targets and loss ratio expectations for designated territory
  • check_circleProvide account servicing for assigned brokers in coordination with Underwriting and Sales teams
  • check_circlePrepare and review case referrals for approval where applicable
  • check_circleCollaborate with internal stakeholders including Claims, Actuarial, and Compliance
  • check_circleEnsure compliance with internal and external standards and implement new protocols
  • check_circleStrategize with territory team members to identify target market segments and strengthen broker relationships
  • check_circleParticipate in quarterly self-audit processes to ensure compliance and implement findings
  • check_circleSupport revenue goals by collaborating with Distribution on retention and new business targets

Requirements

  • verifiedBachelor's degree in Business, Finance, Economics, or related field
  • verifiedMinimum of 8 years of Health Insurance Underwriting experience or 3 years with a Master's degree
  • verifiedMinimum of 3 years of experience working with captive insurance models
  • verifiedProficiency with underwriting software and data analysis tools

Benefits & Perks

check_circlePaid time off for company holidays, vacation, sick and personal dayscheck_circlePaid parental leavecheck_circleMental health services
Ryan Specialty logo
Company

Ryan Specialty

Industry

accounting & finance

View company profilearrow_forwardlanguageWebsite
Quick Overview

Experience

8+ yrs (Senior)

Education

Bachelor's degree in Business, Finance, Economics, or related field required

Job Type

Full-Time

Skills Required

Health Insurance UnderwritingCaptive Insurance ModelsUnderwriting SoftwareData Analysis ToolsRisk AssessmentPricing Methodologies
arrow_forward
Captive Senior Benefits Underwriter at Ryan Specialty is based in Monroe Harbor, 400, East Monroe Street, Jewelers Row, Loop, Chicago, South Chicago Township, Cook County, Illinois, 60603, United States. This is a on-site role.
Is this Captive Senior Benefits Underwriter job remote, hybrid, or on-site?expand_more
Ryan Specialty has listed this Captive Senior Benefits Underwriter role as on-site.
How much experience is required for this Captive Senior Benefits Underwriter role?expand_more
Captive Senior Benefits Underwriter at Ryan Specialty typically requires 8+ years of relevant experience at the senior level.
What skills do you need for the Captive Senior Benefits Underwriter role at Ryan Specialty?expand_more
Key skills for Captive Senior Benefits Underwriter at Ryan Specialty include Health Insurance Underwriting; Captive Insurance Models; Underwriting Software; Data Analysis Tools; Risk Assessment; Pricing Methodologies; Regulatory Compliance; and Policy Development.
What education is required for Captive Senior Benefits Underwriter at Ryan Specialty?expand_more
Educational requirements for this role: Bachelor's degree in Business, Finance, Economics, or related field required; and Master's degree can substitute for 5 years of experience (3 years with Master's instead of 8).
What category does the Captive Senior Benefits Underwriter role belong to?expand_more
Captive Senior Benefits Underwriter at Ryan Specialty is part of the accounting & finance job category on Recrutus.
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Contractor jobsFull-Time jobsIntern jobsOther jobsPart-Time jobsPer-Diem jobsTemporary jobsVolunteer jobs
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Jobs in TexasJobs in CaliforniaJobs in New YorkJobs in FloridaJobs in North CarolinaJobs in OhioAll states →
Top categories
Healthcare & Nursing jobsLogistics & Warehouse jobsEngineering jobsIT jobsSales jobsHospitality & Catering jobsAccounting & Finance jobs
Popular skills
CDL-A jobsExcel jobsEnglish jobsMicrosoft Office jobs
Featured employers
Company
About usFAQContactPrivacy policyUS privacy noticeAccessibility

Recrutus helps candidates discover roles that match their skills and helps teams reach qualified applicants faster. Browse by metro, discipline, or work style — from internships to senior leadership.

© 2026 Recrutus. All rights reserved.
Terms of serviceCookie policyAcceptable useDMCA policyEmployer termsCandidate terms
Regulatory Compliance
Policy Development
Compliance Management
Data Analysis