01/28/2026  
The Sr. Human Resources Manager will work closely with the CHRO, HR Team, and Department Management to support HR functions across the organization. This role will focus on onboarding and developing talent, enhancing employee engagement, and driving organizational effectiveness through data-informed practices, including HR policy, recruitment, employee relations, benefits, compliance, talent development, payroll processes, and technology-enabled automation. EDUCATION AND EXPERIENCE:  Bachelor’s degree in human resources, Business Administration, or related field. 10+ years in management level position with HR generalist experience. SPHR certification preferred.  SKILLS/COMPETENCIES REQUIREMENTS: Strong knowledge of HR principles, employment law, and compliance requirements, including multi-state environments, with demonstrated experience across policy, employee relations, recruiting, and HR metrics. Proven experience overseeing talent development, benefit...
Captive Resources Itasca, IL, USA Full Time
01/27/2026  
The Account Manager works collaboratively with the Underwriting team once binding decisions have been made, owns post sale process through policy issuance, establish files for policy holders, and works with Captive Resources Program Management for new policy holder onboarding. ESSENTIAL EDUCATION AND EXPERIENCE: Bachelor’s Degree or other related discipline, and at least two (2) years of stop loss experience in account management, claims, underwriting, or sales. SKILLS/COMPETENCIES REQUIREMENTS: Group health benefits or related experience Organizational skills and experience with prioritizing project work and tasks Excellent communication skills both verbal and written Proficient in Microsoft Word and Excel Experience with Connexure ELS Office preferred. ESSENTIAL DUTIES AND RESPONSIBILITIES: Serve as primary service contact for assigned stop loss book of business (new business and renewal) including claims payment inquiries, premium remittance and...
Captive Resources Itasca, IL, USA Full Time
01/26/2026  
The Underwriting Analyst is responsible for setting up new and renewal prospects for Stop Loss/Captive Underwriters, as well as performing all other necessary functions required to underwrite the prospect and/or renewal. Heavy involvement in the implementation of materials required for issuance and sold case processing. EDUCATION AND EXPERIENCE:  A bachelor’s degree in business, finance, insurance, mathematics, or a related field.  SKILLS/COMPETENCIES REQUIREMENTS: Knowledge of available employer Stop Loss products, including contract terms and RFP data interpretation Strong mathematical background Ability to handle large volume of work efficiently and correctly with limited errors Strong team attitude Works well independently and in a team environment Interpersonal skills Excellent written and verbal communication skills Strong skills in Microsoft Office, especially using Excel and Word, and other on-line computer systems Comfortable making...
Captive Resources Itasca, IL, USA Full Time
01/26/2026  
The Underwriter is responsible for evaluating and underwriting stop-loss insurance. The role involves analyzing medical risk, pricing policies, and making recommendations based on a thorough understanding of both medical costs and insurance principles. EDUCATION AND EXPERIENCE: A bachelor’s degree in business, finance, insurance, mathematics, or a related field.  2 -5 years of experience in insurance underwriting, preferably in the health insurance or medical stop-loss field. Experience with medical claims analysis, pricing, and risk management is essential. SKILLS/COMPETENCIES REQUIREMENTS: Stay updated on industry trends, regulatory changes, and best practices in medical stop-loss underwriting. Risk management principles and stop-loss insurance products. Medical terminology, healthcare costs, and trends in medical claims. Regulatory and compliance issues in insurance underwriting. Strong analytical and problem-solving abilities. Proficiency in underwriting...
Captive Resources Itasca, IL, USA Full Time
01/26/2026  
The Senior Underwriter is responsible for risk-based underwriting of new and/or existing accounts.  Accountability for the achievement of profit, persistency, and growth goals through financial analysis or employer groups.  EDUCATION AND EXPERIENCE: Bachelor’s Degree in Business or in a related discipline with 5+ years of experience in stop loss underwriting and Captive experience (preferred). SKILLS/COMPETENCIES REQUIREMENTS: Creativity and strong problem solving skills Strong mathematical background Ability to handle large volume of work efficiently and correctly with limited errors Strong team attitude Works well independently and in a team environment Interpersonal skills Excellent written and verbal communication skills Strong skills in Microsoft Office, especially using Excel and Word, and other on-line computer systems Comfortable making presentations to small groups Organization, planning and prioritization skills Strong analytical, problem...
Captive Resources Itasca, IL, USA Full Time
01/23/2026  
The Health Captive Program Manager provides majority of the technical aspects of our health benefit captives.  Maintains a high level of day-to-day client and broker business relationships. Responsible for timely captive financial and claims reporting oversight. Provides underwriting coordination and planning for renewal business.  Works closely with teams and vendors on any captive issues.   ESSENTIAL EDUCATION AND EXPERIENCE: Bachelor’s Degree or equivalency in a related discipline and at least seven (7) years of experience in Health Benefits Account Management, Program Management, Operations, Underwriting, or other Insurance related field.   SKILLS/COMPETENCIES REQUIREMENTS: 7+ years working in Health Insurance Benefits (preferably carrier/broker) Solid understanding of finance and accounting principles Strong analytical, problem solving, and judgment skills Strong team attitude Works well independently and in a team environment Interpersonal skills...
Captive Resources Itasca, IL, USA Full Time
01/22/2026  
We are seeking a Actuarial Consultant to support our growing actuarial consulting practice. This position requires the candidate to work as part of a team of professionals to independently analyze complex problems and develop workable solutions. The candidate will achieve significant interaction and visibility with clients. ESSENTIAL EDUCATION AND EXPERIENCE:  BA/BS degree in actuarial science, mathematics, statistics, computer science, data analytics, economics, finance, business or related field, with an Associate of the Casualty Actuarial Society.  This position requires 4+ years of actuarial experience in the property & casualty industry, with a preference for prior actuarial consulting experience SKILLS/COMPETENCIES REQUIREMENTS: Associate or Fellow of the Casualty Actuarial Society (ACAS or FCAS ). 4+ years of actuarial experience in the property & casualty industry, with a preference for prior actuarial consulting experience. Strong organizational...
Captive Resources Itasca, IL, USA Full Time
01/16/2026  
Execute business marketing strategies, initiate contact with existing and potential customers, identify their needs and sell and manage ongoing services to meet those needs. Assist in developing and facilitating the proposal process for specific brokers/clients including budget and pricing development, proposal writing, contract negotiations, and client presentations. Create and build long term client relationships. Requires extensive out of town travel, including proposal presentations, workshops, and board meetings. ESSENTIAL EDUCATION AND EXPERIENCE:   Bachelor’s Degree in Business, Marketing/Sales, or other related discipline and five to seven (5-7) years of experience in Commercial Insurance business development and underwriting. Experience supporting the development of proposals to brokers/clients. SKILLS/COMPETENCIES REQUIREMENTS: Responsible for developing and implementing individual marketing strategy. Manage and increase membership in assigned accounts....
Captive Resources Itasca, IL, USA Full Time
01/15/2026  
Provides administrative support for the Risk Control Department. Assist with workshop preparation including copying, packet assembly and badges, creating and updating reports, data entry, and direct member support. Assist the Risk Control Department in database management, preparing various reports, and analysis. ESSENTIAL EDUCATION AND EXPERIENCE: Bachelor’s Degree (preferred) with at least three (3) years in Administrative Assistance and Microsoft Office products with proficiency in Access, Excel, Word & PowerPoint SKILLS/COMPETENCIES REQUIREMENTS: Detail oriented. High level of confidentiality. High level of accuracy. Ability to handle deadlines and work under pressure at times. Organizational, planning, and prioritization skills.   Strong analytical, problem solving, and judgment skills.   Works well independently and in a team environment.   Sense of accomplishment.   Strong initiative.   Interpersonal skills and open...
Captive Resources Itasca, IL, USA Full Time
01/13/2026  
Consult with and advise group captive Board of Directors, execute business marketing strategies, support contact with existing and potential customers, identify their needs and manage ongoing services to meet those needs. Assist in developing and facilitating the proposal process for specific brokers/clients including pricing indication development and client presentations. Create and build long term client relationships. Requires extensive out of town travel, including proposal presentations, workshops, and board meetings. ESSENTIAL EDUCATION AND EXPERIENCE: Bachelor’s Degree in Business, Marketing/Sales, or other related discipline and at least five (5) years of experience in Health Insurance business development, underwriting or related. Experience with employee benefits and/or self-funded medical plans. SKILLS/COMPETENCIES REQUIREMENTS: Consult with Board of Directors on captive strategies, review and assess customer needs, and create customer relationships...
Captive Resources Itasca, IL, USA Full Time
01/13/2026  
About Captive Resources Captive Resources (CRI) is the industry-leading consultant to member-owned group captive insurance companies, helping businesses take control of their insurance destiny. Founded in 1985, CRI replaces traditional, one-size-fits-all insurance programs with a member-owned model that bases premiums on each company’s individual loss experience rather than state rates or industry averages. CRI supports dozens of group captives and thousands of member companies across the United States, providing expertise in safety and loss prevention, claims advocacy, risk management, operational oversight, and financial and investment services. Collectively, CRI’s captives represent $5.5 billion in gross premiums and substantial assets under management. CRI is also recognized for its exceptional workplace culture. The company has been named Best Places to Work by Business Insurance (2017–2025), Top Workplaces by the Chicago Tribune (2017–2025), and Top Workplaces in the U.S.A....
Captive Resources Itasca, IL, USA Part Time
01/02/2026  
A cash application specialist handles cash applications for over 40 Captives, totaling over $4.7B of premium. Responsible for reviewing, processing, and analyzing incoming payments. Works with broker partners and internal departments to obtain necessary documentation needed to reconcile unapplied cash. EDUCATION AND EXPERIENCE:  Associate’s degree in business or other related discipline. Accounting or Finance experience required with at least two (2) years of cash-handling experience; within the insurance industry is a plus. SKILLS/COMPETENCIES REQUIREMENTS: Detail oriented. High level of confidentiality. High level of accuracy. Ability to handle deadlines and work under pressure at times. Organizational, planning, and prioritization skills. Strong analytical, problem solving, and judgment skills. Works well independently and in a team environment. Sense of accomplishment. Strong initiative. Interpersonal skills and open communication. Commitment to...
Captive Resources Itasca, IL, USA Full Time
12/30/2025  
The Clinical Risk Manager RN is responsible for providing high quality case management and claims management consulting, including identification, assessment and projections of high-cost cases to assist in the underwriting process. ESSENTIAL EDUCATION AND EXPERIENCE : ASN or BSN in nursing licensed in the State of Residence; at least two (2) years of clinical experience, and at least two (2) years of stop loss or health payer experience. SKILLS/COMPETENCIES REQUIREMENTS: Reviewing stop-loss cases, making recommendations on potential cost of care, including lasers recommendations. Use established guidelines when conducting stop-loss case reviews. Works with underwriting team to identify potential high-risk claimants in new business and renewal groups. Elicits support from sales and account management, and underwriting. Use reporting and risk identification tools on medical and pharmacy claims to assess risk. Assists in responding to inquiries from underwriting...
Captive Resources Itasca, IL, USA Full Time
12/19/2025  
The Claims Services Manager provides day to day claims administration assistance, customer service, dispute resolution, and general claims consultation services to all assigned captive clients. ESSENTIAL EDUCATION AND EXPERIENCE: Bachelor’s Degree or equivalency in a related discipline and at least seven (7) years of experience in Casualty claims handling and/or claims customer service. Construction claims experience preferred. SKILLS/COMPETENCIES REQUIREMENTS: Strong team attitude Works well independently and in a team environment Interpersonal skills Business acumen Excellent written and verbal communication skills Proficient in Microsoft Office, especially using Excel and Word, and other on-line computer systems Utilize PowerPoint to effectively communicate ideas Comfortable giving presentations to audiences of all sizes Organization, planning and prioritization skills Strong analytical, problem solving and judgment skills Strong customer service...
Captive Resources Itasca, IL, USA Full Time
11/21/2025  
The Human Resources Manager will partner closely with senior management to deliver core HR support across the organization. This role focuses on onboarding and developing talent, enhancing employee engagement, and ensuring effective HR operations including employee relations, compliance, and policy administration. The HR Manager will also assist senior leadership with ad-hoc projects, support day-to-day HR activities, and contribute to key organizational initiatives. Please note:  This position is  based in the Cayman Islands , and candidates  must already reside in Cayman and must be Caymanian  to be considered. This role is with  Kensington Management Group , a sister company of Captive Resources. Although the position is posted through Captive Resources the selected candidate will be employed by Kensington and work directly with the Kensington team. Learn more about Kensington here:  https://kensingtonmanagement.ky/introduction EDUCATION AND EXPERIENCE: Bachelor’s...
Captive Resources Itasca, IL, USA Full Time
09/04/2025  
Support Program Management team in the review and evaluation of underwriting information, actuarial reports, and premium collections. Work with Program Management team in responding to member, broker, and service provider requests. Support member development activities by tracking activity in company CRM system and supporting production of proposals. EDUCATION AND EXPERIENCE: Bachelor’s Degree or equivalency in a related discipline and at least two (2) years of experience in the insurance industry. SKILLS/COMPETENCIES REQUIREMENTS: Collaboration – research assignments and validate actions Ability to work independently and communicate activities/outcome with team Responsive to assignments and communication on status Excellent written and verbal communication skills Comfortable making presentations to groups Organization; planning and prioritization skills Strong analytical skills; problem solving and judgment Intellectual curiosity to build an in-depth...
Captive Resources Itasca, IL, USA Full Time