36 trainee jobs found in Chicago

Job Description Sompo has a unique opportunity for a 2026 Sompo Underwriting Trainee in our Chicago, IL office. Our Trainee Program is an 18-month program beginning in July 2026 designed to equip you with the essential business and technical skills needed to build a successful career in insurance. As an Underwriting Trainee you will work alongside the most experienced underwriters in the industry to gain in-depth knowledge of our business units and underwriting philosophy through on-the-job learning, workplace mentoring. Our Trainees work directly on their products’ accounts, building relationships and identifying customers’ needs. This rigorous curriculum also includes training in negotiation, risk analysis and relationship management. Sompo’s Trainee Program serves as a launchpad for career advancement, empowering you to acquire the knowledge and skills essential for success in your respective field. What can I expect as a Underwriting Trainee? On-The-Job Learning...

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...

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.  As part of the broader JAB Pet Services ecosystem, IPH collaborates closely with affiliated companies in the UK and Europe to drive alignment, knowledge sharing, and technology strategy consistency across regions. Job Summary: Independence Pet Holdings (IPH) is seeking a collaborative, results-driven...

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.  As part of the broader JAB Pet Services ecosystem, IPH collaborates closely with affiliated companies in the UK and Europe to drive alignment, knowledge sharing, and technology strategy consistency across regions. Job Summary: Independence Pet Holdings (IPH) is seeking a collaborative, results-driven...

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 the highest level Claims Leaders. This position will interacts with the internal senior management and external business partners and resolves issues, which may be sensitive or confidential in nature and of high visibility. This role will require travel as appropriate to assist Claims Leaders and their broader meetings, strategy sessions and activities. This role will also work very closely/partner with the Executive Assistant to the CAO. JOB DESCRIPTION: Essential Duties & Responsibilities Performs a combination of duties in accordance with departmental guidelines: Proactively anticipate the SVP’s needs,...

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...

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...

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...

Description Summary:   The Commercial Relationship Sales & Service Manager Senior (CML RSS SR) is the primary point of contact for assigned Commercial customers and Relationship Managers. The CML RSS SR works independently and in partnership with the Relationship Manager by providing a best-in-class experience for a diverse Commercial portfolio. The CML RSS SR applies advanced knowledge and understanding of customer and product onboarding to enhance relationship management, retention, and deepening sales. The CML RSS SR provides leadership, guidance, and day to day management over activities performed by other service colleagues or partners. Duties and Responsibilities: First-line decision maker who will mitigate issues/questions being elevated to management and/or resulting in customer impact; keeps Deal Team abreast of material changes and risk. Responsible for identifying, researching, analyzing, and...

With a company culture rooted in collaboration, expertise and innovation, we aim to promote progress and inspire our clients, employees, investors and communities to achieve their greatest potential. Our work is the catalyst that helps others achieve their goals. In short, We Enable Possibility℠. Responsibilities Independently manage assigned Third Party Administrator (TPA) relationship s Address and resolve TPA performance issues in coordination with internal partners (Stat Reporting, Finance, Claims Finance, DQ, Claims IT, Underwriting, Claims, Legal) Collaborate with internal partners to identify and address process gaps or potential efficiencies Manage day to day issues and inquiries from our TPAs and internal partners Complete comprehensive due diligence reviews of potential new TPAs Complete multi-step onboarding process of new TPAs Participate in projects as requested Complete annual TPA reviews, PWC testing and other key initiatives for assigned TPAs Mentor...

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,...

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...

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....

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...

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...

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...

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...

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...

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...

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...