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insurance agent trainee Illinois

24 insurance agent trainee jobs found

Hiscox
06/18/2026  
AVP, Team Manager
Job Type: Permanent Build a brilliant future with Hiscox   About Hiscox USA: Hiscox USA underwrites small- to mid-market commercial risks through brokers, other insurers and distribution partners and directly to businesses. In 2023, gross written premiums for the segment will represent over $1bn. Approximately 50% of the portfolio comprises small commercial business sold either online or through intermediaries, and the remaining 50% represents traditionally traded business intermediated through broking partners for Property and Casualty and Specialty Lines, including Professional Liability, Cyber, Technology and Media & Entertainment. Hiscox USA has built the digital business through ongoing investment in the brand, technology and operational capabilities. The business has pursued an omni-channel approach from its inception and is less constrained by the channel conflict that affects some competitors. Customers have a choice of buying policies online end-to-end, by...
Hiscox Chicago, IL Full Time
Berkley
06/11/2026  
Contract Surety Manager
Company Details   Berkley Surety is a highly professional, service-oriented surety underwriting management company, providing a full spectrum of bonds for contract, environmental, and commercial surety accounts through multiple distribution channels in both the United States and Canada. We write on behalf of W. R. Berkley Corporation member company Berkley Insurance Company, which has an A.M. Best rating of A+ (Superior). We pride ourselves on building strong relationships with our agents. We highly value the insight and expertise our agency partners bring to the table which helps us provide timely and predictable surety solutions.   Company URL:   www.berkleysurety.com  Responsibilities Manage, produce and underwrite new and renewal business from assigned agents/brokers in the primary line of business. Consistently achieve budgeted financial results (premium volume, loss ratio, premium collections and expense management...
Berkley Chicago, IL
CNA
06/10/2026  
System Architect Director - AI Platform Engineering
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 System Architect (SA) Director for AI Platforms Engineering serves as the technical owner for the enterprise AI platform which is the shared foundation powering all AI and GenAI products across the organization. This leader owns the platform's architecture, engineering standards, and delivery roadmap, translating strategic AI capabilities into reliable, scalable, and governed platform capabilities that accelerate every product team building on top of them. Working in close partnership with Enterprise Architects, Product Management, and Release Train Engineers (RTEs), the SA Director ensures that platform investments are tightly aligned to business outcomes, compliance requirements, and...
CNA Chicago, IL Full Time
RLI
06/08/2026  
Associate Underwriter - Executive Products Groups
About Us  We’re not like other insurance companies. From our specialty products to our business model, our culture to our results — we’re different. Different is who we are, and how we work, interact, deliver and succeed together. Creating a different and better insurance experience doesn’t just happen. It takes focus and a shared passion for going beyond the expected to forge relationships and deliver care that makes a difference. This approach rises from and is supported by our talented, ethical and smart team of employee owners united around a single purpose: to work alongside our customers and partners when they need us, in unexpected ways, with exceptional results. Apply today to make a difference with us.  RLI is a Glassdoor Best Places to Work company with a strong, successful background. For decades, our financial track record has been stellar — a testament to our culture and validation of our reputation as an excellent underwriting company....
RLI Chicago, IL Full Time
Encova Insurance
06/03/2026  
Regional Vice President, Commercial Lines
We are seeking a proven insurance leader preferably residing within the listed states within our Midwest territory who have established agency relationships and strong regional market expertise to support our strategic growth initiative. Jurisdictional knowledge and leadership experience in underwriting across the Midwest are strongly preferred. The position will report to a Senior Vice President, Commercial Lines - Small Business Are you a Referral? If you know a current Encova Insurance associate and would like to apply as a referral, please encourage them to submit your referral information before you submit your application. You will receive an email with a direct URL link to the Job Posting of interest. Applying through this URL link will create your referral relationship for our Talent Acquisition Team. Unique residence requirements are listed in each job posting, please review closely for details. Encova is only able to employ associates who reside and work...
Encova Insurance IL Full Time
CNA
06/01/2026  
Underwriting Manager (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: This Underwriting Manager 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 engagement and drive new business growth. If you're ready to stretch your skills and grow your career, we’d love to meet you. Manages an underwriting staff and is accountable for business results through the oversight, analysis, and performance of a renewal portfolio across multiple regions. Under general management direction,...
CNA Chicago, IL Full Time
H.W. Kaufman Group
05/29/2026  
Inside Broker
Responsibilities Summary: When someone needs insurance coverage for the unique, the unusual, or the unconventional, they come to Burns & Wilcox. Burns & Wilcox offers unparalleled resources and exposure for those looking to grow their career in the specialty insurance industry. We are looking for candidates with an entrepreneurial spirit and drive for career advancement to join our team as a Professional Liability Broker.  Build agent and broker relationships, find sources, and be creative in placing risks and identifying product opportunities Handle accounts of all sizes, must be willing to work towards handling larger accounts independently Seek opportunities to access and cultivate new brokerage markets and products Travel and entertain clients and prospects Work independently, while mentoring and training new brokers Develop and submit underwriting referrals, where required, to company brokerage facilities...
H.W. Kaufman Group Chicago, IL Full Time
Hiscox
05/29/2026  
AVP, Team Manager
Job Type: Permanent Build a brilliant future with Hiscox   Position: AVP, Team Manager – GL BI and PD Reporting to: Claims Director, Property & Casualty         Band: II Location: Atlanta, Boston, Chicago, Hartford, New York, Scottsdale Flexibility: Permanent Travel: Hybrid   About Hiscox USA: Hiscox USA underwrites small- to mid-market commercial risks through brokers, other insurers and distribution partners and directly to businesses. In 2023, gross written premiums for the segment will represent over $1bn. Approximately 50% of the portfolio comprises small commercial business sold either online or through intermediaries, and the remaining 50% represents traditionally traded business intermediated through broking partners for Property and Casualty and Specialty Lines, including Professional Liability, Cyber, Technology and Media & Entertainment. Hiscox USA has built the digital business through ongoing investment in the brand, technology...
Hiscox Chicago, IL Full Time
CNA
05/27/2026  
System Architect Director - AI Innovation
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 System Architect (SA) Director has overall technical authority for one or more programs/Agile Release Trains (ARTs) within a portfolio, with direct management accountability for a staff of Engineers and Business Analysts. The SA Director works closely with an Enterprise Architect, Product Management and Release Train Engineer (RTE) to ensure ongoing alignment of technical and business outcomes. The SA Director owns the creation, maintenance and communication of the Architecture, along with implementation by one or more development teams. The SA Director is an expert and champion of Scaled Agile Framework (SAFe) architectural design and development, incrementally building the associated...
CNA Chicago, IL Full Time
Sompo International
05/15/2026  
AVP, E&S Property
Job Description Are you looking for your next opportunity? Sompo has a unique opportunity for an Assistant Vice President in our E&S Property team. Our E&S Property team considers all types of commercial occupancies for catastrophe protection based on individual risk characteristics. We entertain single location risks as well as large schedules of locations and consider risks throughout the US including those located in both catastrophe prone and non-catastrophe prone areas. Location: This position will be based out of our Chicago, IL; New York, NY; Morristown, NJ, Garden City, NY, Purchase, NY and Boston, MA areas. We strive for collaboration, which is why we offer a work environment where our employees thrive and develop long-lasting careers. Our business, your impact, our opportunity: What you’ll be doing: Effectively drive acceptable submission activity and quickly determine acceptability of risk in accordance with...
Sompo International Chicago, IL Full Time
Auto-Owners Insurance
05/09/2026  
Underwriter
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 underwriting trainee to join our team. This job performs and applies insurance coverage, rules and guidelines to execute the underwriting decision-making process according to Company underwriting philosophy. This job includes training and development through completion of the Company’s underwriter training program for the assigned line of insurance and requires the person to: Learn various...
Auto-Owners Insurance Peoria, IL Full Time
Auto-Owners Insurance
05/09/2026  
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 Full Time
Auto-Owners Insurance
05/09/2026  
Auto 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 Peoria, IL Full Time
Independence Pet Group
05/07/2026  
Program Manager, Senior
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...
Independence Pet Group Chicago, IL Full Time
Pet Partners Pet Insurance
05/07/2026  
Program Manager, Senior
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...
Pet Partners Pet Insurance Chicago, IL Full Time
Auto-Owners Insurance
04/28/2026  
Field Investigator - SIU
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 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 an experienced and motivated Field Investigator professional to join our team. The position requires the following, but is not limited to: Investigate, evaluate and determine appropriate disposition of all types of claims arising out of the Company’s business. Provide customer service to agents, insured’s and others in the course of handling claims to their conclusion. Meet with people involved with claims. This includes outside our office environment. Increased role as a trainer/resource for...
Auto-Owners Insurance Mount Vernon, IL Full Time
Allstate
04/28/2026  
Virtual Triage Obvious Total Loss Adjuster
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 The Virtual Triage Obvious Total Loss Adjuster is responsible for delivering exceptional customer service to individuals whose vehicles require repair. This role conducts virtual inspections of vehicle damage—including automobiles, motorcycles, ATVs, and RVs—prepares repair estimates, completes total loss valuations, and negotiates moderately complex (and occasionally more complex) settlements with repair facilities, tow yards, and customers. The adjuster accurately estimates repair times related to rental or loss‑of‑use needs. This...
Allstate IL Full Time
Travelers
04/22/2026  
Senior Construction Surety Underwriter, Account Executive Officer
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 Downers Grove, 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

 

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