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Itasca 4 Chicago 2 Oakbrook Terrace 1 Peoria 1
Full Time medical stop loss underwriter Illinois

9 medical stop loss underwriter jobs found

Captive Resources
01/26/2026  
Underwriter
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 Full Time
Captive Resources
01/26/2026  
Senior Underwriter - Health Solutions
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 Full Time
Captive Resources
05/18/2026  
Underwriting Analyst
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 Full Time
Auto-Owners Insurance
05/09/2026  
Underwriter
A career at Auto-Owners is challenging and rewarding.  Our group of caring associates create financial security by helping individuals and businesses make a new start when a loss occurs. Job Description Applications are accepted on an ongoing basis. An open position may not be available at this time. We offer a merit-based work-from-home program based on job responsibilities. After initial training in-person, you could have the flexibility of work-from-home time as defined by the leadership team. Auto-Owners Insurance, a top-rated insurance carrier, is seeking a motivated underwriting trainee to join our team. This job performs and applies insurance coverage, rules and guidelines to execute the underwriting decision-making process according to Company underwriting philosophy. This job includes training and development through completion of the Company’s underwriter training program for the assigned line of insurance and requires the person to: Learn various...
Auto-Owners Insurance Peoria, IL Full Time
MSIG North American
05/07/2026  
Senior Underwriter - Ocean/Cargo Marine
MSIG USA continues to grow!  Company Overview: MSIG USA is the US-based subsidiary of  MS&AD Insurance Group Holdings, Inc. , one of the world’s top P&C carriers and a global Class 15 insurer, with A+ ratings and a reach that spans 40+ countries and regions. Leveraging our 350-year heritage, MSIG USA brings the financial strength, expertise, and global footprint to offer commercial insurance solutions that address your business’s unique risks. The Cargo/Ocean Marine Underwriter plays a critical role in evaluating, pricing, and managing risks associated with domestic and international cargo shipments. This position supports profitable growth of the marine portfolio by applying sound underwriting judgment, building strong broker relationships, and staying ahead of global trade and logistics trends. Key Responsibilities Underwriting & Risk...
MSIG North American Chicago, IL Full Time
Nationwide
05/04/2026  
Director, Brokerage Excess Underwriting - E&S/Specialty
If you’re passionate about helping people protect what matters most to them at a Fortune 100 company with nearly $70 billion in annual sales, as well as innovating and simplifying processes and operations to provide the best customer value, then Nationwide’s Property and Casualty team could be the place for you! At Nationwide®, “on your side” goes beyond just words. Our customers and partners are at the center of everything we do and we’re looking for associates who are passionate about delivering extraordinary care. Ideal candidate will be located in the Chicago area or broader Illinois/Great Lakes region. Brokerage Excess experience needed; existing broker relationships strongly preferred. #LI-AS1 #LI-remote Job Description Summary Are you a leader who can create, develop and manage a strategy and plan that meets customer service and business goals? If you are driven to achieve top financial goals by managing the insurance underwriting business for a territory or...
Nationwide IL Full Time
MSIG North American
03/19/2026  
Senior Underwriter - Cargo Marine
MSIG USA continues to grow!  Company Overview: MSIG USA is the US-based subsidiary of  MS&AD Insurance Group Holdings, Inc. , one of the world’s top P&C carriers and a global Class 15 insurer, with A+ ratings and a reach that spans 40+ countries and regions. Leveraging our 350-year heritage, MSIG USA brings the financial strength, expertise, and global footprint to offer commercial insurance solutions that address your business’s unique risks. Summary: Produce, underwrite and service profitable Marine business in accordance with all department guidelines.  Assumes a leadership role in the organization to positively influence staff and promote a positive image of MSIG in the marketplace. Develop agency relationships and build a profitable book of business. Essential Functions: Produces, selects and underwrites Marine risks within delegated underwriting authority, including construction, transportation or other classes of Inland Marine as...
MSIG North American Chicago, IL Full Time
Captive Resources
02/12/2026  
AVP, Underwriting Manager
The Assistant Vice President (AVP) Underwriting Manager for Medical Stop Loss Insurance is responsible for leading an underwriting team, developing and implementing underwriting strategies, and managing the underwriting process for assigned captive program(s). This includes overseeing the underwriting of new and renewal business, ensuring underwriting guidelines and delegated authority are followed, managing a team of underwriters, and maintaining profitability while controlling risk. The AVP will work closely with senior management, fronting carriers, actuarial, and sales teams to support business goals and drive performance across the medical stop loss portfolio. ESSENTIAL EDUCATION AND EXPERIENCE : Bachelor’s Degree in Business, Insurance, Finance, or other related discipline, and at least eight (8) years of experience in underwriting with 3 years in a leadership/management role within medical stop loss or health insurance industry.   SKILLS/COMPETENCIES REQUIREMENTS:...
Captive Resources Itasca, IL Full Time
Sun Life
12/02/2025  
Senior Employee Benefits Sales Representative - Illinois
Sun Life U.S. is one of the largest providers of employee and government benefits, helping approximately 50 million Americans access the care and coverage they need. Through employers, industry partners and government programs, Sun Life U.S. offers a portfolio of benefits and services, including dental, vision, disability, absence management, life, supplemental health, medical stop-loss insurance, and healthcare navigation. We have more than 6,400 employees and associates in our partner dental practices and operate nationwide. Visit our website to discover how Sun Life is making life brighter for our customers, partners and communities.   Job Description: Location : We support US flexible working arrangements in the contiguous 48 states, however for this position you must reside in either Illinois or Wisconsin .     At Sun Life, we look for optimistic people who want to make life brighter for our  Clients . We understand...
Sun Life Oakbrook Terrace, IL Full Time

 

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