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Full Time 34
Chicago Trainee Illinois

38 Trainee jobs found in Chicago, IL

BP&C, Shared Services Inc. (American National & Argo Group)
04/15/2026  
Underwriting Trainee, Casualty
Company 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 Underwriting Trainee, Casualty Argo /Farm Family currently has an exciting opportunity for an Underwriter Trainee to join our team. This is a production underwriting position responsible for marketing, underwriting, and processing of our Casualty line of business. This role will work on-site 5x per week at our Chicago or New York City office location. The primary duties and responsibilities of the role are: Under supervision, analyze and underwrite new and renewal submissions. Learn and develop an understanding of the professional lines insurance marketplace. This includes policy contract language and intent. Take accounts...
BP&C, Shared Services Inc. (American National & Argo Group) Chicago, IL
RLI
06/08/2026  
Associate Underwriter - Executive Products Groups
About Us  We’re not like other insurance companies. From our specialty products to our business model, our culture to our results — we’re different. Different is who we are, and how we work, interact, deliver and succeed together. Creating a different and better insurance experience doesn’t just happen. It takes focus and a shared passion for going beyond the expected to forge relationships and deliver care that makes a difference. This approach rises from and is supported by our talented, ethical and smart team of employee owners united around a single purpose: to work alongside our customers and partners when they need us, in unexpected ways, with exceptional results. Apply today to make a difference with us.  RLI is a Glassdoor Best Places to Work company with a strong, successful background. For decades, our financial track record has been stellar — a testament to our culture and validation of our reputation as an excellent underwriting company....
RLI Chicago, IL Full Time
Berkley
06/11/2026  
Contract Surety Manager
Company Details   Berkley Surety is a highly professional, service-oriented surety underwriting management company, providing a full spectrum of bonds for contract, environmental, and commercial surety accounts through multiple distribution channels in both the United States and Canada. We write on behalf of W. R. Berkley Corporation member company Berkley Insurance Company, which has an A.M. Best rating of A+ (Superior). We pride ourselves on building strong relationships with our agents. We highly value the insight and expertise our agency partners bring to the table which helps us provide timely and predictable surety solutions.   Company URL:   www.berkleysurety.com  Responsibilities Manage, produce and underwrite new and renewal business from assigned agents/brokers in the primary line of business. Consistently achieve budgeted financial results (premium volume, loss ratio, premium collections and expense management...
Berkley Chicago, IL
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
Sompo International
04/28/2026  
VP, Midwest Regional Manager: Commercial Property
Job Description Are you looking for your next opportunity?   Sompo has a unique opportunity for a Vice President and Midwest Regional Manager o n our Commercial Property Middle Market team.   Our Commercial Property Middle Market team offers property coverage to commercial accounts with a focus on mid to larger mid-size U.S. domiciled companies across a broad base of occupancy types, including but not limited to: Light & Heavy Manufacturing, Food Processing, Metal Working, Warehousing, Retail Stores, Wholesale Suppliers, Hospitals & Healthcare, Educational Institutions, Transportation. The Middle Market Commercial Specialty Property team offers both 100% single carrier capacity and quota share capacity.  We take a collaborative approach to loss control and work closely with our Risk Control Engineers to mitigate risk and partner with our clients to protect their business value. We seek to build long-term relationships with our retail brokers and...
Sompo International Chicago, IL Full Time
Liberty Mutual
06/22/2026  
Senior Underwriter, Cyber Technology Errors & Omissions
Description Ironshore’s Cyber Retail team is seeking an experienced underwriter to support a growing retail portfolio focused on Primary Cyber, Tech E&O, and related cyber liability products. This role underwrites SME, middle‑market, and select large‑complex risks placed through retail brokers in the Midwest.  The ideal candidate has strong retail broker relationships, takes initiative to source and develop new submissions, and can independently underwrite accounts across a range of sizes and complexities while maintaining consistent underwriting discipline and portfolio-focused decision-making.   Depending on experience, we are considered candidates for our Senior or Executive-level Underwriting positions.   Responsibilities   Manages portfolio of brokers/agents & clients. Leverages market presence and expertise to develop and underwrite profitable business, acting as a representative for Liberty. Has relationships with...
Liberty Mutual Chicago, IL Full Time
Hiscox
06/18/2026  
AVP, Team Manager
Job Type: Permanent Build a brilliant future with Hiscox   About Hiscox USA: Hiscox USA underwrites small- to mid-market commercial risks through brokers, other insurers and distribution partners and directly to businesses. In 2023, gross written premiums for the segment will represent over $1bn. Approximately 50% of the portfolio comprises small commercial business sold either online or through intermediaries, and the remaining 50% represents traditionally traded business intermediated through broking partners for Property and Casualty and Specialty Lines, including Professional Liability, Cyber, Technology and Media & Entertainment. Hiscox USA has built the digital business through ongoing investment in the brand, technology and operational capabilities. The business has pursued an omni-channel approach from its inception and is less constrained by the channel conflict that affects some competitors. Customers have a choice of buying policies online end-to-end, by...
Hiscox Chicago, IL Full Time
AIG
06/18/2026  
Regional Production Specialist Sr, Excess & Surplus Lines
Join us as a Senior Regional Production Specialist to grow your career at the forefront of Lexington Healthcare insurance. Make your mark in Lexington Healthcare AIG’s Lexington Insurance Company is the leading US-based surplus lines insurer. For over 50 years, it has provided flexible solutions to companies and organizations of all sizes – from Fortune 100 corporations to small and middle market entities. Lexington is renowned for its ability to help brokers find solutions to the most challenging insurance needs of their clients. Drawing on their entrepreneurial spirit, colleagues are encouraged each day to rise to challenges and embrace opportunities to make a difference. How you will create an impact The Senior Regional Production Specialist manages all Healthcare underwriting within an assigned Branch Office and handles referral decisions for the most complex portfolios. This role takes on a strategic component in the development, implementation and evaluation of...
AIG Chicago, IL Full Time
HUB International
06/14/2026  
Private Client Placement Coordinator
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 450 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 environment...
HUB International Chicago, IL Full Time
Allstate
06/12/2026  
Property Adjuster - Field Estimating - Chicagoland, IL
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 A day in the life of a Field Property Adjuster, and what it takes to do the job! As a Field Property Adjuster, you will be dedicated to providing exceptional service to our policyholders. Your primary responsibility will involve traveling to our customers' homes to conduct on-site inspections, investigate coverage, prepare estimates, and settle claims promptly and efficiently. Additionally, you will handle virtual claims countrywide, leveraging various platforms and software such as Xactimate and ClaimsX Video Collaboration. Your...
Allstate Chicago, IL Full Time
CNA
06/12/2026  
AI Identity and Access Management Consulting Director
You have a clear vision of where your career can go. And we have the leadership to help you get there.  At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.  The Consulting Director, AI Identity & Access Management (IAM) is a strategic and hands-on leader responsible for advancing CNA’s modern IAM capabilities through the application of artificial intelligence, automation, and next-generation identity governance. This role focuses on governing AI agents as non-human identities, driving intelligent automation, and improving end-user experience across IAM services. The position partners across Security, AI Governance, Engineering, and Business teams to ensure AI-enabled identity solutions are secure, scalable, and aligned with enterprise governance standards. JOB DESCRIPTION: Key Responsibilities AI Identity Governance (Core Pillar)...
CNA Chicago, IL Full Time
CNA
06/10/2026  
System Architect Director - AI Platform Engineering
You have a clear vision of where your career can go. And we have the leadership to help you get there.  At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.  The System Architect (SA) Director for AI Platforms Engineering serves as the technical owner for the enterprise AI platform which is the shared foundation powering all AI and GenAI products across the organization. This leader owns the platform's architecture, engineering standards, and delivery roadmap, translating strategic AI capabilities into reliable, scalable, and governed platform capabilities that accelerate every product team building on top of them. Working in close partnership with Enterprise Architects, Product Management, and Release Train Engineers (RTEs), the SA Director ensures that platform investments are tightly aligned to business outcomes, compliance requirements, and...
CNA Chicago, IL Full Time
Allstate
06/04/2026  
Property Adjuster - Field Estimating - Chicago, IL
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 A day in the life of a Field Property Adjuster, and what it takes to do the job! As a Field Property Adjuster, you will be dedicated to providing exceptional service to our policyholders. Your primary responsibility will involve traveling to our customers' homes to conduct on-site inspections, investigate coverage, prepare estimates, and settle claims promptly and efficiently. Additionally, you will handle virtual claims countrywide, leveraging various platforms and software such as Xactimate and ClaimsX Video Collaboration....
Allstate Chicago, IL Full Time
Allstate
06/01/2026  
Large Loss Property Adjuster - Field Estimating - Chicago, IL
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 A day in the life of a Large Loss Field Property Adjuster, and what it takes to do the job! As a Large Loss Field Property Adjuster, you will be dedicated to providing exceptional service to our policyholders. Your primary responsibility will involve traveling to our customers' homes to conduct on-site inspections, investigate coverage, prepare estimates, and settle claims promptly and efficiently. Additionally, you will handle virtual claims countrywide, leveraging various platforms and software such as Xactimate and ClaimsX...
Allstate Chicago, IL Full Time
CNA
06/01/2026  
Underwriting Manager (Underwriting Hub)
You have a clear vision of where your career can go. And we have the leadership to help you get there.  At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.  JOB DESCRIPTION: This Underwriting Manager position is part of the Underwriting Hub—a growing team designed to provide expanded underwriting capabilities for the organization. We will elevate underwriting excellence through streamlined processes, strategic focus, and collaborative growth that enables our field underwriting teams to deepen agent and broker engagement and drive new business growth. If you're ready to stretch your skills and grow your career, we’d love to meet you. Manages an underwriting staff and is accountable for business results through the oversight, analysis, and performance of a renewal portfolio across multiple regions. Under general management direction,...
CNA Chicago, IL Full Time
H.W. Kaufman Group
05/29/2026  
Inside Broker
Responsibilities Summary: When someone needs insurance coverage for the unique, the unusual, or the unconventional, they come to Burns & Wilcox. Burns & Wilcox offers unparalleled resources and exposure for those looking to grow their career in the specialty insurance industry. We are looking for candidates with an entrepreneurial spirit and drive for career advancement to join our team as a Professional Liability Broker.  Build agent and broker relationships, find sources, and be creative in placing risks and identifying product opportunities Handle accounts of all sizes, must be willing to work towards handling larger accounts independently Seek opportunities to access and cultivate new brokerage markets and products Travel and entertain clients and prospects Work independently, while mentoring and training new brokers Develop and submit underwriting referrals, where required, to company brokerage facilities...
H.W. Kaufman Group Chicago, IL Full Time
Hiscox
05/29/2026  
AVP, Team Manager
Job Type: Permanent Build a brilliant future with Hiscox   Position: AVP, Team Manager – GL BI and PD Reporting to: Claims Director, Property & Casualty         Band: II Location: Atlanta, Boston, Chicago, Hartford, New York, Scottsdale Flexibility: Permanent Travel: Hybrid   About Hiscox USA: Hiscox USA underwrites small- to mid-market commercial risks through brokers, other insurers and distribution partners and directly to businesses. In 2023, gross written premiums for the segment will represent over $1bn. Approximately 50% of the portfolio comprises small commercial business sold either online or through intermediaries, and the remaining 50% represents traditionally traded business intermediated through broking partners for Property and Casualty and Specialty Lines, including Professional Liability, Cyber, Technology and Media & Entertainment. Hiscox USA has built the digital business through ongoing investment in the brand, technology...
Hiscox Chicago, IL Full Time
CNA
05/28/2026  
Underwriting Associate(Commercial Construction P&C)
You have a clear vision of where your career can go. And we have the leadership to help you get there.  At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.  Under broad supervision, responsible for underwriting risk for the underwriting lifecycle from submission through policy issuance, for both renewal and new business within limited authority. Partnering with Underwriters on all aspects of the Underwriting function including: providing the necessary information to allow for UW to make prudent underwriting decisions. JOB DESCRIPTION: Performs a combination of duties in accordance with departmental guidelines: 1. Performs underwriting analysis and documentation to determine acceptability of risk in accordance with company guidelines and standards for renewal and new business  within assigned Letter of Underwriting Authority. 2.  Handles...
CNA Chicago, IL Full Time
CNA
05/27/2026  
System Architect Director - AI Innovation
You have a clear vision of where your career can go. And we have the leadership to help you get there.  At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.  The System Architect (SA) Director has overall technical authority for one or more programs/Agile Release Trains (ARTs) within a portfolio, with direct management accountability for a staff of Engineers and Business Analysts. The SA Director works closely with an Enterprise Architect, Product Management and Release Train Engineer (RTE) to ensure ongoing alignment of technical and business outcomes. The SA Director owns the creation, maintenance and communication of the Architecture, along with implementation by one or more development teams. The SA Director is an expert and champion of Scaled Agile Framework (SAFe) architectural design and development, incrementally building the associated...
CNA Chicago, IL Full Time
AIG
05/20/2026  
Account Risk Engineering supervisor
Why Join Risk Consulting at AIG?   Risk Consulting at AIG is about teamwork! It is about utilizing your resources, working together to solve real world problems, and making a positive impact on our client’s futures. When asked, “why do we enjoy what we do?” The answer is simple, the people.   The role of an Account Risk Engineer is critical to what we do at AIG, both as a risk management resource to our clients and as a leading global insurance organization. Account Risk Engineers are responsible for working with clients to identify and mitigate risks to their business such as fire, flood, windstorm, equipment breakdown etc.  A Day in the Life   Looking for variety and a challenge? Client’s range in size, scope, and complexity. One day you may be discussing the loss prevention strategy on an account with an underwriter, the next, surveying a manufacturing plant or diving into the contingent business interruption risks of an account. The key to success isn’t about being...
AIG Chicago, IL Full Time

 

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