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Illinois 33
Chicago Full Time trainee

33 trainee jobs found in Chicago

GEICO
07/31/2026  
Auto Damage Trainee (Field)
Why Join GEICO? 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 on relentless innovation to exceed our customers' expectations while making a real impact on local communities nationwide.   Founded in 1936, GEICO is a member of the Berkshire Hathaway family of companies and one of the largest auto insurers in the United States. 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. Please note: This is not a remote role; you will be required to work in the territory listed on the job posting.   Your Impact at GEICO            As a Field   Auto Damage Trainee,   you’ll...
GEICO Chicago, IL Full Time
Travelers
08/06/2026  
Underwriting Professional Development Program, National Accounts - October 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 Full Time
UFG Insurance
08/05/2026  
Surety Underwriter
UFG is hiring for a Surety Underwriter who will actively working towards building and maintaining a profitable mix of new and existing surety business by developing and maintaining strong working relationships with the agency force.   Demonstrate strong analytical skills to evaluate risks for acceptability within their authority and company underwriting parameters.  Make regular agency visits and calls to assess growth and profitability of agents in their territory.  Prospect and appoint new quality agents in the territory.  Visit current and potential contractor’s place of business to better assess acceptability and quality of the accounts.  **The ideal candidate will reside in Chicago, Illinois/Greater Chicago area or the Milwaukee, Wisconsin territory** Essential Duties and Responsibilities:   Underwrite new submissions and existing accounts utilizing authority granted by head of Surety and with assistance from mentors. Evaluate and assess financial...
UFG Insurance 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
Core Specialty
08/09/2026  
Commercial Surety Regional Manager
- The Commercial Surety Regional Manager is responsible for the underwriting, marketing, production, profitability, and overall management of a regional Commercial Surety portfolio. This position serves as the senior underwriting leader for the assigned territory and is accountable for achieving premium growth, underwriting profitability, agency development, and portfolio management objectives. The Regional Manager will develop and maintain strong relationships with agents, brokers, principals, indemnitors, and other business partners while exercising significant underwriting authority and ensuring compliance with company underwriting guidelines and risk appetite. The position is highly market-facing and focused on profitable business development, agency management, and underwriting execution. Key Accountabilities/Deliverables: Underwriting Leadership Serve as lead underwriter for the assigned territory. Analyze, evaluate, and approve commercial surety...
Core Specialty Chicago, IL Full Time
HUB International
08/07/2026  
Account Manager - Employee Benefits
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 600 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 that...
HUB International Chicago, IL Full Time
AIG
08/03/2026  
Production Specialist, Sr., Excess & Surplus Lines
At AIG, we are reimagining the way we help customers to manage risk. Join us as an Senior Production Specialist, Lexington Healthcare 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 Lexington Healthcare AIG Healthcare has an opportunity for a Senior Production Specialist, specializing in Medical Malpractice and General Liability. The Specialist will be required to underwrite Primary, Umbrella and Excess lines of business. Work effectively both independently and as part of a team to successfully manage their book of business along with contributing to the overall profitability of the malpractice business portfolio. A Senior Production Specialist must be able to illustrate sufficient technical analysis, have a strong underwriting acumen combined with the necessary sales and marketing skills to achieve profitable growth targets. Candidate must have the ability and willingness to...
AIG Chicago, IL Full Time
CNA
08/03/2026  
Executive/Staff Assistant
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 performs administrative support to senior staff. Interacts with internal senior management and external business partners and resolves issues, which may be sensitive or confidential in nature and of high visibility. JOB DESCRIPTION: Essential Duties & Responsibilities Performs a combination of duties in accordance with departmental guidelines: Coordinates, handles and resolves business unit problems and customer issues independently and proactively escalating as appropriate. Provides outstanding customer serivce, acting with the appropriate sense of urgency. Coordinates special projects for senior management, collaborating with others as needed....
CNA Chicago, IL Full Time
HUB International
08/01/2026  
Technology Change Manager
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 The Opportunity At HUB International, the Technology Change Manager...
HUB International Chicago, IL Full Time
Allstate
07/30/2026  
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 provide 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 expertise will be...
Allstate Chicago, IL Full Time
Liberty Mutual
07/29/2026  
Executive Underwriter, Inland Marine
Description The Executive Underwriter will grow and develop a book of complex construction-focused inland marine risks—from builders risk and installation projects to contractors’ equipment and large-scale infrastructure developments. Applies deep technical judgment, market insight, and data-driven analysis to evaluate project exposures, select profitable business, and develop appropriate coverage, terms, conditions, deductibles, limits, and pricing within established underwriting authority. For the most complex, unusual, or high-line-size accounts, partners with senior leaders and internal experts to develop creative, disciplined solutions that protect Liberty Mutual’s portfolio while supporting the success of construction clients. Responsibilities Underwrite and manage construction-focused business:  Evaluate builders risk, installation, contractors’ equipment, project cargo, and infrastructure accounts, considering project scope, construction type,...
Liberty Mutual Chicago, IL Full Time
CCC Intelligent Solutions
07/28/2026  
Vice President, APD Sales
Salary range is: $217,236.65 - $225,000.00 This position is equity and bonus and/or commission eligible. CCC Intelligent Solutions Inc. (CCC) is a leading cloud platform for the multi-trillion-dollar insurance economy , creating intelligent experiences for insurers, repairers, automakers, part suppliers, and more. At CCC, we’re making life just work by empowering more than 35,000 businesses with industry-leading technology to get drivers back on the road and to health quickly and seamlessly. We’re pushing boundaries with innovative AI solutions that simplify and enhance the claims and repair journey. Through purposeful innovation and the strength of its connections, CCC technologies empower the people and industry relied upon to keep lives moving forward when it matters most. Learn more about CCC at www.cccis.com .   The Role We are seeking a proven sales leader to accelerate the adoption, expansion, and commercial success of our Automobile Physical Damage (APD)...
CCC Intelligent Solutions Chicago, IL Full Time
CNA
07/24/2026  
Senior Product Owner, Large Property
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 Senior Product Owner serves as the customer proxy to the Agile team within the agile process and is the final authority for decisions regarding priority, business value, and functionality for all the work done by the Agile development team. The Senior Product Owner has the ability to analyze complex cross functional business processes and define integrated user stories using industry standard techniques and is able to apply modified approaches and techniques to meet different circumstances. In partnership with their Scrum Master, the Senior Product Owner will monitor metrics and suggest new ways of increasing quality and verify the business value delivered by the team. The Senior Product...
CNA Chicago, IL Full Time
CNA
07/22/2026  
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.  JOB DESCRIPTION: 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. 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....
CNA Chicago, IL Full Time
CNA
07/22/2026  
Senior Product Owner
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.  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, business value, and functionality for all the work done by the Agile development team. The Senior Product Owner has the ability to analyze complex cross functional business processes and define integrated user stories using industry standard techniques and is able to apply modified approaches and techniques to meet different circumstances. In partnership with their Scrum Master, the Senior Product Owner will monitor metrics and suggest new ways of increasing quality and verify the business value delivered by the team. The Senior...
CNA Chicago, IL Full Time
CNA
07/17/2026  
Underwriting Director (Technology 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.  JOB DESCRIPTION: For over three decades, CNA has been a trusted provider of insurance solutions for technology companies of all sizes—from emerging startups to global enterprises—across software, IT services, hardware, media, and telecommunications. Our Global Technology Practice delivers specialized coverages, including Technology Errors & Omissions (Tech E&O), Cyber Liability, and comprehensive international solutions, complemented by our traditional Property & Casualty capabilities. With deep industry expertise, flexible underwriting capabilities, and a collaborative approach, we design innovative insurance programs tailored to each client’s unique risk profile. CNA...
CNA Chicago, IL Full Time
Allstate
07/17/2026  
Large Loss Contents Property Adjuster - 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 Large Loss Contents Property Adjuster: You will be traveling to customer’s home to inspect large loss contents claims. Handle escalated claims files that have complex contents. Conduct a thorough coverage investigation of the loss and ensure the policy was applied correctly. You will be on site inspecting as well as using advanced video technology to collaborate with onsite vendors to identify damages and write a contents damage estimate. Communicate empathetically with customers and help them...
Allstate Chicago, IL Full Time
Liberty Mutual
07/13/2026  
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
Allstate
07/06/2026  
Catastrophe Field Property Adjuster- Chicago Area
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 Join Allstate as a CAT Field Property Adjuster and make a real impact when it matters most. We’re hosting onsite interviews on the week of August 17th in our Chicago Suburban office, offering you the chance to meet our hiring team in person and discover how you can join Allstate’s trusted catastrophe claims team. Don’t miss this limited opportunity to take the next step in your career! As a Catastrophe Field Property Adjuster, you will play a crucial role in inspecting properties damaged by various perils, including wind, hail,...
Allstate Chicago, IL Full Time
H.W. Kaufman Group
07/04/2026  
Senior Underwriter, Commercial Insurance
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

 

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