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Chicago Trainee

41 Trainee jobs found in Chicago

BP&C, Shared Services Inc. (American National & Argo Group)
04/15/2026  
Underwriting Trainee, Casualty
Company 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 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 through...
BP&C, Shared Services Inc. (American National & Argo Group) Chicago, IL
HUB International
02/06/2026  
M&A Integration Trainer
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.  Join one of the top acquiring firms as an M&A Integration...
HUB International Chicago, IL Full Time
CNA
04/17/2026  
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 accounts within limited authority. Works independently on a high volume of accounts, applying sound underwriting judgment and collaborating with Underwriters as needed. Partners across the Hub to ensure accurate documentation, pricing execution, and responsive service. This Underwriting Associate 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...
CNA Chicago, IL Full Time
AmTrust Financial
04/16/2026  
Senior Underwriter
Overview The Senior Underwriter administers the underwriting, servicing of new, and renewal accounts for agents and producers assigned within the territory in compliance with company underwriting, authority, and pricing standards. Maintains a solid understanding of AmTrust’s mission, vision, and values. Upholds the standards of the AmTrust organization.   We are open to candidates with backgrounds in either renewal or new business. Whether your experience is focused on managing and growing established books or driving new business development, we value transferable underwriting and relationship‑management skills and are open to varied career paths into this role. Responsibilities Quickly and effectively make underwriting decisions based on review and analysis of renewal policy. Make sure policy characteristics are based on company pricing and underwriting guidelines. Collaborate closely with other team members, sales and...
AmTrust Financial Chicago, IL Full Time
Huntington
04/16/2026  
Private Bank Analyst - Portfolio Manager
Description Summary: The Private Bank Analyst - Portfolio Mgr is an entry level position and involves learning all aspects of successfully managing a portfolio of client household relationships and the associated delivery of high quality services with the intention of moving into the next level position within 24 months and being responsible for the sales goals of that Level I position.  Duties and Responsibilities: The Analyst will be trained in an investment and Portfolio Manager role, along with a broad knowledge of sales and service capabilities.  Excellent networking and new client acquisition skills need to be developed in anticipation of moving into a sales role.  Engages the appropriate practice specialty professionals to provide the fully integrated delivery of comprehensive Private Bank services.  Responsible for supporting high client service levels, strong retention and suitable contribution to...
Huntington Chicago, IL Full Time
Liberty Mutual
04/15/2026  
Executive 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.   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 senior/market-leading brokers and/or key agents. Maintains a strong market presence, including established relationships with agents...
Liberty Mutual Chicago, IL Full Time
Ryan Specialty
04/14/2026  
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
CNA
04/11/2026  
Underwriting Associate, National Accounts Casualty, Captives
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 Captives 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   3-4   days per week from our office in Chicago.   Job Description   Performs a combination of duties   in...
CNA Chicago, IL Full Time
Allstate
04/11/2026  
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
HUB International
04/11/2026  
Senior Workday HRIS Analyst
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 the 5th 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 more than 19,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions. Overview of Position: The Senior HR Tech...
HUB International Chicago, IL Full Time
Ryan Specialty
04/10/2026  
Senior Project Manager
Position Summary The Project Manager is responsible for overseeing the planning, execution, and delivery of various projects within the organization, ensuring they align with strategic goals and meet stakeholder expectations. The role drives scalable process improvements and innovations within the designated business, leading strategic initiatives, and overseeing project documentation. They identify and mitigate risks, monitor progress, facilitate communication between teams, and resolve conflicts to ensure smooth project progression. What will your job entail? Job Responsibilities: • Develops detailed project plans defining project scope, outlining tasks, timelines, milestones, and resources required. Drives scalable and sustainable process improvements, innovation, and automations within the designated business. • Drives scope and deliverable definition, project team formation, planning and scheduling, resource and cost assessments, communication, and issue monitoring and...
Ryan Specialty Chicago, IL Full Time
Liberty Mutual
04/08/2026  
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 Full Time
The Hartford
04/07/2026  
Excess Casualty Wholesale Account Manager
Account Manager - OA09HN We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future.              This role will have a Hybrid work schedule, with the expectation of working in an office (Chicago, IL, Scottsdale, AZ, Frisco, TX, Greenwood Village, CO, Morristown, NJ, New York, NY, Red Bank, NJ) 3 days a week (Tuesday through Thursday). The Account Manager, as part of Global Specialty Operations, will serve as a critical partner to the Primary Casualty and Excess Casualty Wholesale underwriting teams. The individual focuses on service experience & book of business management, while also acting as a key contact for brokers and underwriters. This is an individual contributor role without supervisory responsibilities, also mentors and train less...
The Hartford Chicago, IL Full Time
HUB International
03/31/2026  
HR Coordinator
Job Description The HR Coordinator is a key member of the HR Support Services team, responsible for delivering high-quality, timely, and customer-focused support throughout the employee lifecycle. Reporting to the Lead, HR Support Services, this role handles a broad range of both complex and basic administrative tasks and service requests, including onboarding, employee changes, offboarding, records management, and Tier 1 and Tier 2 HR inquiries and escalations. This role is ideal for a detail-oriented, service-minded professional looking to grow within a collaborative and fast-paced HR environment supporting 20,000+ employees across North America.  Key Responsibilities   Employee Lifecycle Administration   Process both complex and basic employee lifecycle transactions including new hires, job changes, terminations, leaves of absence, and employee status updates.  Coordinate pre-boarding and onboarding logistics, such as background checks, new hire...
HUB International 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
CNA
03/27/2026  
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, The Senior Product Owner is an individual contributor who serves as the customer proxy for one or more Agile development teams supporting Corporate Legal, Claims, and Compliance. The Senior Product Owner is the final authority for decisions regarding priority, business value, and functionality for work delivered by the team(s), ensuring outcomes align with enterprise objectives as well as legal, regulatory, and policy requirements. The Senior Product Owner analyzes complex, cross‑functional business processes spanning Legal,...
CNA Chicago, IL Full Time
Ryan Specialty
03/26/2026  
Senior Accountant
Position Summary The Senior Accountant will contribute significantly to the growth and operational excellence of our organization by supporting a broad range of accounting and financial reporting activities. This role operates within a highly collaborative, cross-functional environment and serves as a key member of the Revenue team. The Senior Accountant will be responsible for executing both GAAP and non-GAAP revenue reporting requirements while ensuring the accuracy and integrity of financial information. What will your job entail? Responsibilities: Assist in the timely preparation of financial reporting on a monthly, quarterly, and annual cycle Review and record transactions in accordance with GAAP and ASC 606 Preform monthly, quarterly, and annual revenue reconciliations Collaborate with various departments to ensure accurate contract review and billing Prepare journal entries and revenue-related schedules Assist with internal and external audits by...
Ryan Specialty Chicago, IL Full Time
Allstate
03/15/2026  
Legal Support Apprentice
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 position is only open to candidates currently pursuing their associates degree from a community college or trade school. Those currently pursuing their bachelors degree or higher will not be considered for this role. Early Career Apprentice Program Want to work in your field and train on the job? Join our 12–24-month apprentice program! You will earn and learn on the job, receive career guidance and mentorship, all while attending school. Allstate will also provide tuition assistance and hands-on training in customer...
Allstate Chicago, IL Part Time
Allstate
03/15/2026  
Business Systems Apprentice
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 position is only open to candidates currently pursuing their associates degree from a community college or trade school. Those currently pursuing their bachelors degree or higher will not be considered for this role. Early Career Apprentice Program Want to work in your field and train on the job? Join our 12–24-month apprentice program! You will earn and learn on the job, receive career guidance and mentorship, all while attending school. Allstate will also provide tuition assistance and hands-on training in customer...
Allstate Chicago, IL Part Time
Allstate
03/15/2026  
Business Process Consultant Apprentice
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 position is only open to candidates currently pursuing their associates degree from a community college or trade school. Those currently pursuing their bachelors degree or higher will not be considered for this role. Early Career Apprentice Program Want to work in your field and train on the job? Join our 12–24-month apprentice program! You will earn and learn on the job, receive career guidance and mentorship, all while attending school. Allstate will also provide tuition assistance and hands-on training in customer...
Allstate Chicago, IL Part Time

 

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