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Illinois 29
Chicago Full Time Trainee

29 Trainee jobs found in Chicago

Berkshire Hathaway GUARD
04/24/2026  
Senior Territory Manager (Illinois)
Overview Good Things Start Here.   Good things are happening at Berkshire Hathaway GUARD Insurance Companies—an A+ (Superior) rated, nationwide Property & Casualty insurer backed by Berkshire Hathaway. With supportive leadership, collaborative teams, and opportunities to grow, GUARD is a place where people build meaningful, long‑term careers.   Good Things You Can Count On. Competitive pay + generous PTO Medical, dental & vision starting day one 401(k), tuition reimbursement & longevity bonuses Responsibilities We are seeking a Senior Territory Manager for our Illinois Territory.  This individual will be responsible for agency relationships and business development, with a strong focus on the marketing of GUARD’s products and developing the territory across their assigned footprint. This is a role for an experienced high-performing territory manager who excels at finding pockets of opportunities,...
Berkshire Hathaway GUARD Chicago, IL Full Time
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
Allstate
04/21/2026  
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
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
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
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
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
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...
Ryan Specialty Chicago, IL Full Time
HUB International
03/15/2026  
Sr. Manager, M&A Integration Training and OCM
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 Senior Manager, M&A Integration Training...
HUB International Chicago, IL 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 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 Full Time
Origami Risk
02/26/2026  
(Senior) Technical Sales Consultant - Insurance
Overview As a (Senior) Technical Sales Consultant on our Claims team, you will seek to understand detailed customer needs and define how Origami Risk solutions can meet those needs both in RFPs and in person. Technical Sales Consultants are responsible for configuring and presenting complex solution demonstrations and leading technical discussions.    Starting base pay for this role is between $100,000 and $150,000. The actual base pay is dependent upon many factors, such as transferable skills, work experience, business needs, training, location, and market demands. The base pay range is subject to change and may be modified in the future. This role will be eligible for a bonus as well as competitive medical, dental, and vision benefits, wellness reimbursement, life insurance, and a 401(k) with company match. We offer vacation and sick leave benefits (under a flexible time off policy in most states). Responsibilities...
Origami Risk Chicago, IL Full Time
BP&C, Shared Services Inc. (American National & Argo Group)
02/06/2026  
Associate Actuary I
Company Farm Family Farm Family specializes in farm and ranch protection with a wide range of products including flexible farm packages, business owner policies, commercial package, workers compensation, commercial auto and select personal auto coverage. Farm Family is a leader in serving the Northeast and Mid-Atlantic markets and is pursuing growth across the U.S. The Farm Family entities are wholly-owned subsidiaries of Clearbrook Group Holdings Inc. 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,...
BP&C, Shared Services Inc. (American National & Argo Group) Chicago, IL Full Time
HUB International
01/28/2026  
Strategic Account Executive - Personal 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 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

 

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