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Chicago, IL underwriting trainee

29 underwriting trainee jobs found in Chicago, IL

Travelers
03/12/2026  
Underwriting Professional Development Program, Technology - June 2026
Who Are We? Taking care of our customers, our communities and each other. That’s the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 170 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it. Job Category Underwriting Compensation Overview The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program,...
Travelers Chicago, IL, USA Full Time
GEICO
02/17/2026  
Auto Damage Trainee
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. Auto Damage Trainee – Chicago, IL “ *Starting pay rate varies based upon position and location. Ask your Recruiter for details!” Accidents can be scary, and our Auto Damage team rises to the occasion to provide unparalleled customer service when our customers need us the most. We’re looking for Auto Damage Trainees in Chicago, IL who are motivated and ready to grow their careers to the next level...
GEICO Chicago, IL, USA Full Time
Westfield
10/13/2025  
WSP IT Intern, Chicago Office (2026 Summer)
The Westfield Specialty Intern Program is a paid, ten-week program that offers students the opportunity to obtain firsthand insight into the insurance business.  Every day you'll learn and develop your skills but you'll also have a clear and supportive path ahead of you. You'll gain the confidence to take on real projects, build your network and learn from senior leaders across our business.   We are seeking Intern candidates to work with our Information Technology team in our Chicago, IL or Berkeley Heights, NJ  offices.       Program Elements Include: Classroom and On The Job Training  Weekly Lunch and Learn Series with Senior Leaders Formal Mentor Program  Presentations from Major Brokerage Partners  Teambuilding and Social Activities; including Community Service Event Industry based Group Project    Participants in the Westfield Specialty Summer Intern Program are immersed in the day-to-day operations of a fast-moving, growing insurance...
Westfield Chicago, IL, USA Full Time
Ryan Specialty
09/22/2025  
Underwriter, E&S Property
Position Summary Join Our Team of Forward-Thinking Underwriters! Are you a recent RMI graduate or an industry professional ready to take the next step in your underwriting career? Velocity is looking for driven, collaborative individuals to underwrite E&S Specialty Property Insurance: covering high-impact perils like hurricanes, earthquakes, tornadoes, and fires across the U.S. About Velocity Velocity, recently acquired by Ryan Specialty, is a cutting-edge managing general underwriter (MGU) specializing in E&S insurance for the U.S. specialty commercial property market. Innovation is at the core of everything we do. We rapidly connect risk with capital, tackling market challenges with agility and purpose. Our mission is to expand access to global capital for property and business owners, especially in underserved areas. By partnering with brokers, agents, and top-tier capital providers, we combine deep industry expertise with advanced data analytics and technology to...
Ryan Specialty Chicago, IL, USA Full Time
Reliance Matrix
03/05/2026  
Client Management Trainee Program
Job Responsibilities and Requirements Launch your career with momentum.  The STAR (Service Training and Readiness) Program at Reliance Matrix is your fast track into a dynamic, high‑impact career in Client Management . This one‑year immersive program is built for individuals who are hungry to learn, eager to grow, and ready to jump into a role where relationships, strategy, and results matter. As a STAR Associate, you’ll gain hands‑on experience, build your industry expertise, and sharpen your sales and service skills — all while collaborating with leaders who are invested in your success. You won’t just observe the business… you’ll contribute to it. Successful completion of the program propels you directly into a Client Management position , where your earning potential and career growth are truly unlimited. Program Overview From day one, you’ll be part of a high‑performing team that will challenge you, support you, and help you grow. Throughout the program,...
Reliance Matrix Schaumburg, IL, USA
Auto-Owners Insurance
01/27/2026  
Field Claims Representative
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 claims trainee to join our team. This job handles entry-level insurance claims under close supervision through the life-cycle of a claim including but not limited to: investigation, evaluation, and claim resolution. This job provides service to agents, insureds, and others to ensure claims resolve accurately and timely. This job includes training and development completion of the Company’s...
Auto-Owners Insurance Schaumburg, IL, USA Full Time
GEICO
03/09/2026  
Auto Damage Trainee
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.  Auto Damage Trainee –Kenosha/Racine, WI Salary: $30.53 per hour / $61,500 annually Accidents can be scary, and our Auto Damage team rises to the occasion to provide unparalleled customer service when our customers need us the most. We’re looking for Auto Damage Trainees in Kenosha/Racine, WI who are motivated and ready to grow their careers to the next level with GEICO. Flexibility to work in...
GEICO Kenosha, WI, USA Full Time
CNA
03/13/2026  
Underwriting Associate - 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.  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, USA Full Time
AIG
03/10/2026  
Regional Production Specialist, Excess & Surplus Lines
About the role The Regional Production Specialist must be able to illustrate the highest levels of technical proficiency and underwriting acumen combined with marketing and sales skills to meet production underwriting goals while maintaining budgeted loss and expense ratios. Candidates are expected to work effectively in a team environment to develop broker and portfolio strategies in addition to working independently to manage a profitable book of new and renewal business. The Head of Property for the Zone will rely heavily on this position to assist in guiding, mentoring and training more junior members of the team, as well as to assist in planning and budgeting, collaboration across AIG divisions and building a culture of diversity and inclusion across the team. What you need to know: The candidate must have the ability to underwrite property risks across the spectrum of E&S Property business while helping to set direction for your team and maintaining a balanced...
AIG Chicago, IL, USA Full Time
CNA
03/06/2026  
Underwriting Associate, Nat'l Accounts Casualty - Wholesale
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: Joining the   National Accounts   Casualty   Wholesale   team as an Underwriting Associate, you will   be   responsible for   underwriting risk for the underwriting lifecycle   both   r enewal   and new   business within limited authority.    You will   partner   with Underwriters   as well as   maintain   branch and broker relationships   on all aspects of the Underwriting function   including   providing the necessary information to allow   the   Underwriter   to make prudent underwriting decisions .      This hybrid position works 3 days per week from   our   office   in...
CNA Chicago, IL, USA Full Time
CNA
03/06/2026  
Distribution Operations Analyst
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: The Distribution Operations Analyst on the Distribution Enablement team is responsible for supporting CNA regions, business units, underwriters, and external distribution partners, including brokers, across distribution and agency operations. Collaborates with Underwriting resources to educate them on contracts, applications and processes that impact agency experience and production. Partners with Underwriting resources and Brokers to understand and analyze agency issues and develop solutions to provide high quality internal and external service and experience. The ideal candidate is a recent college graduate seeking to begin a long‑term career in insurance...
CNA Chicago, IL, USA Full Time
CNA
03/04/2026  
Senior Product Owner, Actuarial
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.  Are you passionate about data and innovative technology? CNA’s Analytics organization is looking for candidates who want to use cutting edge, cloud-based technology to deliver valuable insights to our business teams. The Data & Analytics Solution Hub combines the best of IT, Analytics and Data Engineering in order to innovate and deliver at the pace of a start-up. This role is aligned with the Actuarial Value Stream team, which delivers complex data assets used by the Actuarial department and others in the organization. An individual contributor that serves as the customer proxy to the Agile team within the agile process and is the final authority for decisions regarding priority,...
CNA Chicago, IL, USA Full Time
H.W. Kaufman Group
02/27/2026  
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, USA Full Time
AIG
02/20/2026  
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...
AIG Chicago, IL, USA Full Time
H.W. Kaufman Group
02/13/2026  
Underwriter, Private Client
  *This position is open to multiple Burns & Wilcox branch offices across the US.*   When retail agents and brokers have successful clients who require coverage for the unique, the unusual, or the unconventional, they come to the Private Client Practice at Burns & Wilcox. Our Underwriters have full underwriting authority to build and grow a profitable book of Private Client business across the US and Canada.  Burns & Wilcox offers unparalleled resources and exposure for those looking to excel in the specialty insurance career.  Interested? Join our team! Responsibilities Build a growing book of profitable Private Client business Manage agency relationships and serve as lead client contact Provide a Best in Class customer service experience for our retail partners Execute on the national marketing strategy to increase new and renewal business Work within granted authority and program guidelines to...
H.W. Kaufman Group Chicago, IL, USA Full Time
BP&C, Shared Services Inc. (American National & Argo Group)
02/06/2026  
Associate Actuary I
Argo Group and Farm Family are specialty property and casualty insurance brands whose underwriting companies are wholly owned subsidiaries of Brookfield Wealth Solutions, a leading provider of wealth and insurance solutions. Argo and Farm Family partner with agents and brokers to help businesses stay in business, delivering collaborative insurance solutions for niche markets. Job Description Associate Actuary I, Farm Family Insurance At Farm Family, we invite you to step into a pivotal role as Associate Actuary I, where your expertise goes beyond the ordinary, and you become a driving force behind innovative actuarial solutions. Make Your Mark at Farm Family As an Associate Actuary I, you will build on your existing actuarial skillset and take on broader, more diverse responsibilities and enjoy greater autonomy in your work. You can be based in our Chicago, Omaha, New York City, Springfield (MO), or Albany (NY) office. At Farm Family, you’ll discover the...
BP&C, Shared Services Inc. (American National & Argo Group) Chicago, IL, USA Full Time
Liberty Mutual
02/02/2026  
Executive Underwriter, Wholesale Miscellaneous Professional Liability
Description Executive Underwriter — Miscellaneous Professional Liability: Acts as the leading technical authority for Miscellaneous Professional Liability (MPL) across an aligned wholesale territory, working independently and autonomously subject to required process oversight. Serves as the go‑to advisor on MPL coverage, exposures and wordings for colleagues across the segment, including senior underwriting leaders. Underwrites MPL policies within delegated authority, making acceptance and declination decisions based on analytical, data‑driven assessment of submitted information and pricing the risk appropriately. Typical exposures include E&O claims for consultants, IT/service providers and other non‑class specific professionals, media/communications risks, and other miscellaneous advisory or service professions. Where applicable, may be responsible for setting the business plan and portfolio strategy for the MPL book in their territory. Responsibilities...
Liberty Mutual Chicago, IL, USA Full Time
Independence Pet Group
01/14/2026  
Technology Program Manager - Global Transformation
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.    Job Summary:  Independence Pet Holdings (IPH) is undertaking a multi-year enterprise transformation to modernize its insurance technology ecosystem and build a scalable, digital-first operating model across its MGAs.  The Sr. Technology Program Manager, Global Transformation will lead the...
Independence Pet Group Chicago, IL, USA Full Time
Pet Partners Pet Insurance
01/14/2026  
Technology Program Manager - Global Transformation
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.    Job Summary:  Independence Pet Holdings (IPH) is undertaking a multi-year enterprise transformation to modernize its insurance technology ecosystem and build a scalable, digital-first operating model across its MGAs.  The Sr. Technology Program Manager, Global Transformation will lead the...
Pet Partners Pet Insurance Chicago, IL, USA Full Time
AIG
01/09/2026  
Senior Field Risk Engineer
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 a Field Risk Engineer is core to what we do at AIG, both as a risk management resource to our clients and as a leading global insurance organization. Field 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? Property loss prevention surveys range in size and scope. One day you may be looking at a metal working facility, the next, a university campus. The key to success isn’t about being the expert in every occupancy, it’s about building trust and cross-functional relationships with stakeholders through...
AIG Chicago, IL, USA Full Time

 

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