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Chicago health and benefits senior associate

47 health and benefits senior associate jobs found in Chicago

HUB International
05/19/2026  
Actuarial Consultant
Job Description ABOUT US At HUB International, we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. HUB is a global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions. ABOUT THE ROLE The Actuarial...
HUB International Chicago, IL Full Time
Applied Systems
05/03/2026  
Associate AI Engineer / AI Engineer
Job Description Amazing Career Moments Happen Here     Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable, we’re creating a place where amazing career moments are made possible.      Position Overview      We're seeking an  Associate AI Engineer / AI Engineer  to build and enhance data solutions and AI initiatives for the business of insurance. In this role, you will work closely with the Principal Data Architect, Data Scientists, and Software Engineers to build, model, and maintain data solutions as we optimize data architecture and...
Applied Systems Chicago, IL
Ryan Specialty
04/22/2026  
Senior Data Analyst
Position Summary We are looking for a contract Senior Data Analyst to join a project that is projected to run through the end of the year. In this role, you will be responsible for analytic data needs, handling complex data projects. What will your job entail? *This is a contract/temporary role that will be tentatively running through the remainder of this year* Key Responsibilities Analyze, extract, transform, and reconcile large, complex datasets across multiple internal systems and external data sources. Provide analytical support for operational areas including claims, policy, client, and underwriting data. Identify trends, anomalies, risks, and improvement opportunities through data analysis; clearly communicate findings and recommended actions to leadership. Develop, maintain, and automate recurring and ad hoc reports, dashboards, and management deliverables. Model and analyze data using SQL, Excel, Access, and enterprise data warehouse tools. Build and...
Ryan Specialty Chicago, IL Full Time
GEICO
03/27/2026  
Senior Director, FP&A
At GEICO, we offer a rewarding career where your ambitions are met with endless possibilities.  Every day we honor our iconic brand by offering quality coverage to millions of customers and being there when they need us most. We thrive through relentless innovation to exceed our customers’ expectations while making a real impact for our company through our shared purpose.  When you join our company, we want you to feel valued, supported and proud to work here. That’s why we offer The GEICO Pledge: Great Company, Great Culture, Great Rewards and Great Careers. GEICO is one of the nation's largest and fastest-growing auto insurers thanks to our low rates, outstanding service and clever marketing. We're an industry leader employing thousands of dedicated and hard-working associates. As a wholly owned subsidiary of Berkshire Hathaway, we offer associates training and career advancement in a financially stable and rewarding workplace. At GEICO, we offer a rewarding...
GEICO Chicago, IL Full Time
Allstate
03/09/2026  
Associate, Opportunistic, Strategic Ventures
At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection.  Job Description This role offers a unique opportunity to gain diverse experience across two dynamic areas within Allstate Investments: Strategic Ventures and Opportunistic Investments. Participants will develop a broad skill set in research, financial analysis, investment strategies, and deal structuring, while building valuable networks within the industry. This program is ideal for those looking to accelerate their career growth, gain exposure to different facets of the business, and contribute to strategic initiatives that drive Allstate's success....
Allstate Chicago, IL Full Time
HUB International
02/22/2026  
ERISA Counsel
ABOUT US     At   HUB International , we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to   maintain   their own unique, regional culture while   leveraging   support and resources from our corporate centers of excellence.        HUB is   one of the   largest global insurance and employee benefits   broker , providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over   $5 billion   in revenue and almost   20,000 employees   in 600 offices throughout North America, HUB has   grown substantially, in   part due to our...
HUB International Chicago, IL Full Time
WTW
02/01/2026  
Senior Director, Executive Compensation and Board Advisory
Summary As a Senior Director in the Executive Compensation and Board Advisory practice you will be primarily responsible for selling, leading and delivering large client engagements and serving as a strategic advisor to clients in your areas of subject matter expertise. You’ll also contribute your thought leadership to the overall development of the Executive Compensation practice and act as a coach and mentor for fellow colleagues. Specific client engagements could include the following: Executive compensation benchmarking Short and long-term incentive design Compensation Committee advice/support Board Advisory Working closely with colleagues in other Work & Rewards practices to sell and deliver on broader rewards strategy projects, including our broad-based employee solutions (compensation, careers, skills, etc.), and our proprietary data and software solutions Partnering with colleagues in our other Health, Wealth, and Career...
WTW Chicago, IL Full Time
Huntington
12/19/2025  
Commercial P&C Insurance Sales Executive Senior - Chicago, IL
Description Summary: The Insurance Sales Executive Senior – Commercial P&C is a high-impact, commission-based sales role offering significant income potential. This position requires strong consultative selling skills, effective communication, and a deep understanding of the insurance industry. We provide a comprehensive three-year income transition plan to support your success from day one. The ideal candidate will be skilled in pursuing and closing sales in the Commercial Property and Casualty space, particularly with clients in the $50M–$500M+ revenue range. Expertise across all lines of commercial P&C insurance—including loss sensitive and group captive insurance programs—is essential. A strong focus on business development and strategic growth is critical to success in this role. Key Responsibilities: Drive business development by identifying and cultivating new client opportunities through internal...
Huntington Chicago, IL Full Time
HUB International
08/24/2025  
Senior Account Manager and Team Lead - Commercial Lines
About HUB    In a rapidly changing world, HUB advises businesses and individuals on how to prepare for the unexpected. As one of the world’s largest insurance brokers, our focus is dedicated to providing our customers with the peace of mind that what matters most will be protected — through unrelenting advocacy and tailored insurance solutions that put our clients in control. Our growing team of professionals across North America represents a broad, deep, and one-of-a kind aggregation of entrepreneurs and leaders recognized for their excellence throughout the insurance community.     Why Choose HUB?    Throughout our network of more than 550 HUB offices in North America, we offer a competitive, exciting, and friendly work environment that strategically positions our employees for longevity and success. At HUB, we believe in investing in the future of our employees and provide continuous opportunities for growth and development .   Our entrepreneurial culture fosters an...
HUB International Chicago, IL Full Time
H.W. Kaufman Group
08/14/2025  
Senior Commercial Lines Underwriter
Responsibilities Build, maintain, and grow a book of business Manage agency relationships and serve as lead client contact Create and execute marketing plan to increase new and renewal business Rate, quote and bind each risk to determine acceptability, coverage, and pricing for large or complex renewals as well as new business Develop and submit underwriting referrals to company brokerage facilities and Burns & Wilcox management   Monitor key metrics to formulate corrective action impacting new business hit, renewal retention, premium growth, and loss ratio Lead, train, and develop Assistant and Associate Underwriters Qualifications Bachelor’s degree or equivalent combination of education and experience   Minimum 3 years of commercial lines underwriting or brokerage experience required, excess & surplus experience preferred Demonstrated proficiency in sales and marketing...
H.W. Kaufman Group Chicago, IL Full Time
AIG
06/25/2025  
Senior Executive Underwriter, AIGRM
At AIG, we are reimagining the way we help customers to manage risk. Join us as a Senior Executive Underwriter to play your part in that transformation. It’s an opportunity to grow your skills and experience as a valued member of the team. Make your mark in AIG Risk Management, AIGRM. AIG underwriting teams help to find insurance solutions in areas including Financial Lines, Property, Casualty, Specialty Lines, Cyber, Multinational Clients, and High Net Worth individuals. We are reimagining how we help customers to manage risk, transforming our operating model, and reshaping our role responsibilities and career pathways. The goal is to unlock the full potential in each colleague – empowering our people to grow as insurance professionals and add more value to our customers and AIG. How you will create an impact This role may supervise a group of Senior and Associate Underwriters, including designing and monitoring work, development of underwriting and/or marketing...
AIG Chicago, IL Full Time
BP&C, Shared Services Inc. (American National & Argo Group)
05/19/2026  
VP, Ceded Reinsurance
Company Shared Services Argo and Farm Family are specialty property and casualty insurance brands whose underwriting companies are wholly-owned subsidaries of Clearbrook Holdings Inc. Argo and Farm Family partner with agents and brokers to provide insurance solutions that enable businesses to manage risks with confidence. Job Description The VP, Ceded Reinsurance leads the end-to-end execution of outwards treaty reinsurance placements for Clearbrook Group Holdings, Inc. across all property and casualty lines.  This role is a strategic partner to the business, supporting the unique needs of Argo Casualty, Argo Specialty, Farm Family, and Runoff segments. You will be responsible for structuring complex reinsurance programs, managing global broker and reinsurer relationships, and ensuring the group’s capital and balance sheet interests are protected through robust risk transfer strategies.  Placement Strategy + Execution End-to-end placement: lead the lifecycle of...
BP&C, Shared Services Inc. (American National & Argo Group) Chicago, IL Full Time
BP&C, Shared Services Inc. (American National & Argo Group)
05/19/2026  
Senior Inland Marine Technical Claims Specialist
Company Argo Group Argo Group is an underwriter of specialty insurance products in the property and casualty market. Argo offers a full line of products and services designed to meet the unique coverage and claims-handling needs of businesses. The Argo entities are wholly-owned subsidiaries of Clearbrook Group Holdings Inc. Job Description Summary:    We are looking for a highly capable Senior Inland Marine Technical Claims Specialist to join our team and work from any of the following Argo offices: Albany, Chicago, Houston, Los Angeles, Omaha, Richmond (VA). We work together in the office five days a week in order to strengthen our culture, build team connections, and drive profitability. This role adjudicates our most complex inland marine claims for our customers, such as Builder’s Risk, Contractor’s Equipment and Motor Truck Cargo. This is a 100% in-office position. Candidates must be able to work on-site at a designated company office during standard...
BP&C, Shared Services Inc. (American National & Argo Group) Chicago, IL Full Time
Sompo International
05/15/2026  
AVP, E&S Property
Job Description Are you looking for your next opportunity? Sompo has a unique opportunity for an Assistant Vice President in our E&S Property team. Our E&S Property team considers all types of commercial occupancies for catastrophe protection based on individual risk characteristics. We entertain single location risks as well as large schedules of locations and consider risks throughout the US including those located in both catastrophe prone and non-catastrophe prone areas. Location: This position will be based out of our Chicago, IL; New York, NY; Morristown, NJ, Garden City, NY, Purchase, NY and Boston, MA areas. We strive for collaboration, which is why we offer a work environment where our employees thrive and develop long-lasting careers. Our business, your impact, our opportunity: What you’ll be doing: Effectively drive acceptable submission activity and quickly determine acceptability of risk in accordance with...
Sompo International Chicago, IL Full Time
Dual North American - Howden Group Holdings
05/13/2026  
Associate Underwriter Windstorm Risk
At DUAL North America, our core values dictate how we live and work. We are a group with independence and people at its heart and we are a home for talent with a unique culture: the biggest small company in the world. The focus on being a People First business has always been at the very heart of the Group; Our vision was to create an independent business with a unique culture and one that would survive and thrive as a business controlled by the people working for it. And finding the most talented and entrepreneurial people to join the Group has been and will continue to be key. DUAL North America, Inc. is seeking a Associate Underwriter Windstorm Risk Classification : Full-Time Division : Windstorm Risk Salary : $70,000.00-$85,000.00 Travel : 0-10% Work Environment : Hybrid Location : Chicago, IL Role overview DUAL North America is seeking an Associate Underwriter for the Windstorm Risk division.   At DUAL, Associate Underwriters play a key supportive...
Dual North American - Howden Group Holdings Chicago, IL Full Time
BP&C, Shared Services Inc. (American National & Argo Group)
05/08/2026  
Senior Underwriter, Inland Marine
Company Argo Group Argo Group is an underwriter of specialty insurance products in the property and casualty market. Argo offers a full line of products and services designed to meet the unique coverage and claims-handling needs of businesses. The Argo entities are wholly-owned subsidiaries of Clearbrook Group Holdings Inc. Job Description A Brief Overview Argo Group currently has a challenging opportunity for a Senior Underwriter in their Inland Marine line of business.  This is a production underwriting position responsible for marketing, underwriting and processing assigned lines of business. Responsibilities may also include participating in special projects and mentoring less experienced staff.   The role will work onsite (5 days per week) at our Chicago office location. The primary duties and responsibilities of the role are:   Underwrite and analyze new business and renewal submissions for our assigned area.  Ensure our marketing initiatives are...
BP&C, Shared Services Inc. (American National & Argo Group) Chicago, IL Full Time
Dual North American - Howden Group Holdings
05/08/2026  
Associate Underwriter Windstorm Risk
At DUAL North America, our core values dictate how we live and work. We are a group with independence and people at its heart and we are a home for talent with a unique culture: the biggest small company in the world. The focus on being a People First business has always been at the very heart of the Group; Our vision was to create an independent business with a unique culture and one that would survive and thrive as a business controlled by the people working for it. And finding the most talented and entrepreneurial people to join the Group has been and will continue to be key. DUAL North America, Inc. is seeking a Associate Underwriter Windstorm Risk Classification : Full-Time Division : Windstorm Risk Salary : $70,000.00-$85,000.00 Travel : 0-10% Work Environment : Hybrid Location : Chicago, IL Role overview DUAL North America is seeking an Associate Underwriter for the Windstorm Risk division.   At DUAL, Associate Underwriters play a key supportive...
Dual North American - Howden Group Holdings Chicago, 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
Allstate
05/01/2026  
Learning & Development Senior Consultant II
At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection.  Job Description Allstate is currently seeking an L&D Senior Consultant II based in Chicago, IL to support Global Learning and Development. This role is responsible for facilitating leadership and employee development through engaging and impactful learning experiences aligned with enterprise and business unit strategies. It emphasizes equipping individuals with the skills needed to drive business outcomes while ensuring programs are customer-centered, efficient, and cost-effective. If you have a strong background in facilitation, enjoy developing...
Allstate Chicago, IL Full Time
Allstate
04/29/2026  
Employee Engagement Senior Consultant II (On-Site)
At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection.  Job Description The Enterprise Employee Engagement Senior Consultant II supports a cohesive culture, coordinates most employee engagement initiatives across the office, The Enterprise Employee Engagement Senior Consultant II will be helping to create and advocate for a positive and innovative culture by assisting in developing, managing and executing all projects supporting these values. This role utilizes subject matter knowledge to be a resource for team members on employee culture, researching trends, best practices and processes that contribute to...
Allstate Chicago, IL Full Time

 

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