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Chicago trainee Illinois

32 trainee jobs found in Chicago, IL

Westfield
10/01/2026  
WSP Actuarial Intern, Chicago
The Westfield Specialty Intern Program is a paid, ten-week program that offers students the opportunity to obtain firsthand insight into the insurance business.  Every day you'll learn and develop your skills but you'll also have a clear and supportive path ahead of you. You'll gain the confidence to take on real projects, build your network and learn from senior leaders across our business.  The 2027 Summer Intern Program will run from June 7th to August 13th.     We are seeking Intern candidates to work with our Actuary team in our Chicago, IL  office.      Program Elements Include: Classroom and On The Job Training  Weekly Lunch and Learn Series with Senior Leaders Formal Mentor Program  Presentations from Major Brokerage Partners  Teambuilding and Social Activities; including Community Service Event Industry based Group Project    Participants in the Westfield Specialty Summer Intern Program are immersed in the day-to-day operations of...
Westfield Chicago, IL Full Time
Westfield
09/22/2026  
2027 Summer Intern Program- IT Intern, Chicago
The Westfield Specialty Intern Program is a paid, ten-week program that offers students the opportunity to obtain firsthand insight into the insurance business.  Every day you'll learn and develop your skills but you'll also have a clear and supportive path ahead of you. You'll gain the confidence to take on real projects, build your network and learn from senior leaders across our business.  The 2027 Summer Intern Program will run from June 7th to August 13th.    We are seeking Intern candidates to work with our Information Technology team in our Chicago, IL or Berkeley Heights, NJ  offices.      Program Elements Include: Classroom and On The Job Training  Weekly Lunch and Learn Series with Senior Leaders Formal Mentor Program  Presentations from Major Brokerage Partners  Teambuilding and Social Activities; including Community Service Event Industry based Group Project    Participants in the Westfield Specialty Summer...
Westfield Chicago, IL Full Time
Westfield
09/22/2026  
2027 Summer Intern Program- Underwriting Intern, Chicago
The Westfield Specialty Intern Program is a paid, ten-week program that offers students the opportunity to obtain firsthand insight into the insurance business.  Every day you'll learn and develop your skills but you'll also have a clear and supportive path ahead of you. You'll gain the confidence to take on real projects, build your network and learn from senior leaders across our business.  The 2027 Summer Intern Program will run from June 7th to August 13th.     Program Elements Include: Classroom and On The Job Training  Weekly Lunch and Learn Series with Senior Leaders Formal Mentor Program  Presentations from Major Brokerage Partners  Teambuilding and Social Activities; including Community Service Event Industry based Group Project    Participants in the Westfield Specialty Summer Intern Program are immersed in the day-to-day operations of a fast-moving, growing insurance company. You will gain valuable, hands-on experience and insurance...
Westfield 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
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
AIG
10/10/2026  
Senior Underwriting Assistant
The Senior Underwriting Assistant is an individual contributor within the Underwriting Support Unit of the unit’s field operations.  This role assists the underwriters by screening risk offerings and with pre and post-binding processes. The role also performs services including problem-solving or research projects requiring broad insurance and/or procedural knowledge and works under direct supervision. This role will work on our AIG Captives business line. In addition to the traditional UA duties, this role will: Support regional UA Manager in overseeing all daily business activities and act as the first point of call for all UAs in the region Review new submissions against prescribed criteria to determine if risk qualifies for LOB risk appetite.  Triages submission for missing information and follows up with the broker for outstanding items. Performs a comparison of renewal submission information against prior year information and documents differences for...
AIG Chicago, IL Full Time
Allstate
10/08/2026  
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...
Allstate Chicago, IL Full Time
UFG Insurance
10/07/2026  
Sr Production Underwriter - Middle Market
UFG is looking for a   Sr. Production Underwriter - Middle Market to join our Great Lakes Region in a multi-line, multi-industry opportunity.  In this role you will be responsible for attracting and underwriting middle market business, deploying effective account management while fostering strong working relationships with agency partners. This role executes underwriting strategy to achieve profit and premium plans. The Sr. Production Underwriter will handle a renewal book in their territory as assigned. This role assists with the resolution of escalated issues, and mentors and coaches team members.   While this is a remote opportunity, the ideal candidate will reside within Minnesota or Wisconsin. Responsibilities:   Profitably underwrite complex new and renewal business through risk selection, pricing, contractual integrity, and account management, in accordance with delegated authority, and ensuring regulatory compliance. Demonstrate critical thinking in...
UFG Insurance Chicago, IL Full Time
Ryan Specialty
10/07/2026  
Director I, Catastrophe Modeling
Position Summary The Director I of Catastrophe Modeling leads catastrophe risk analytics for the Central Underwriting organization, sitting at the intersection of modeling science, data engineering, and underwriting strategy. This role owns both the technical execution of cat modeling (RMS, AIR) and the tooling, pipelines, and automation that make that modeling fast, accurate, and scalable — while building and managing the team that delivers it. The Director translates portfolio-level model output into underwriting guidance, sets technical standards for the function, and represents catastrophe risk analytics to underwriting and executive leadership. What will your job entail? What You’ll Do Team & Strategic Leadership Build, manage, and mentor a team blending catastrophe modeling analysts and technical/automation developers. Mentor, guide, and train portfolio modeling managers across the team, building bench strength and consistent technical standards for the...
Ryan Specialty Chicago, IL Full Time
Freeway Insurance Services America
10/05/2026  
District Sales Manager
Our Perks: Commission & Monthly Bonus Eligibility Recognition Culture & Leadership Development Competitive Vacation & Sick Time Package Comprehensive Benefits package including medical, dental, vision and life insurance Retirement Plan: A 401K plan with a percentage of company-matched contributions Fitness: We reimburse up to $10 a month to an employee for their gym Employee Assistance Program: Confidential assistance to you or anyone in your household who is experiencing personal or professional problems — at no cost Extra Perks: Access to disability, hospital indemnity, health advocate program, universal life, critical illness, and accident insurance plans. We even offer pet insurance Our Company: Confie and its family of companies - Freeway, Baja, Bluefire & others - is one of the largest privately held insurance brokers in the United States and has been ranked the #1 Personal Lines Leader by the Insurance Journal for the seventh...
Freeway Insurance Services America Chicago, IL Full Time
Ryan Specialty
09/23/2026  
Senior Director Catastrophe Risk
Position Summary The Senior Director of Catastrophe Modeling leads catastrophe risk analytics for Ryan Alternative Risks, an Alternative Risk Transfer (ART) organization built around parametric structures, facultative and treaty reinsurance, and multi-year contracts. This is a distinct discipline from traditional portfolio cat modeling, and the role offers an experienced modeler the chance to apply deep technical skill to novel, structurally complex risk. The Senior Director sits at the intersection of modeling science, data engineering, and underwriting strategy, owning both the technical execution of cat modeling (RMS, AIR) and the tooling, pipelines, and automation that make that modeling fast, accurate, and scalable — while building and managing the team that delivers it. The Senior Director translates portfolio-level model output into underwriting guidance, sets technical standards for the function, and represents catastrophe risk analytics to underwriting and executive...
Ryan Specialty Chicago, IL Full Time
CNA
09/23/2026  
Underwriting Director - Cyber/E&O - Midwest
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.  Leads and directs an underwriting group and is accountable for business results through overall management, profitability, and business development of a book of Cyber/E&O business throughout the Midwest. In conjunction with senior management, works within the highest limits of authority. Has regional, industry, segment, or company-wide scope of responsibility. JOB DESCRIPTION: Essential Duties & Responsibilities Performs a combination of duties in accordance with departmental guidelines: Directs the work activities and has full management responsibility for the performance and development of subordinate staff in accordance with corporate strategic direction. Onboards,...
CNA Chicago, IL Full Time
AF Group
09/17/2026  
Senior Loss Control Consultant
SUMMARY Responsible for providing consultation and training to employers regarding safety matters. Develop business partnership and ambassador-type relationship with insured policyholders. Evaluate physical premises, equipment, materials, work practices, and safety policies and programs.  Conduct safety surveys of employers’ premises to gather information to assist in risk selection as an integral part of the underwriting process.  Work with management to develop loss control strategies that will have the greatest impact on company success measures. This position involves field-based work requiring travel within the assigned market/territory. Residency within or in close proximity to the designated market is required to support job responsibilities.   Identify potentially hazardous conditions and unsafe acts that may have an adverse impact on employee claims and assist the client in reducing or eliminating those hazardous condition or unsafe acts. Review business...
AF Group Chicago, IL Full Time
Liberty Mutual
09/15/2026  
Executive Underwriter, Property
Description We are seeking an Executive Underwriter to manage and maintain a significant portion of our Major Accounts Property portfolio in the Central Region. In this role, you will be responsible for handling complex monoline Property accounts with minimum TIVs of $100m, analyzing the customer's property exposures, hazards, financial information, requested coverages, loss history, pricing targets and desired program structure to select business and determine appropriate terms and conditions. Will work closely with Risk Engineering to produce and manage a profitable book of business and manage producer/customer relationships. Maintains the highest level of skills/knowledge in the large property space with average account annual premium of around $1m. Shares underwriting expertise with other underwriters and stakeholders across all levels.   Responsibilities Manages portfolio of brokers/agents & clients. Leverages market presence and expertise to...
Liberty Mutual Chicago, IL Full Time
CNA
09/04/2026  
Underwriting Associate(Commercial Construction 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.  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...
CNA Chicago, IL Full Time
CNA
09/04/2026  
Administrative Assistant II
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 general supervision performs complex administrative support on day to day operational matters in an operations, corporate services, or sales area. Interacts and resolves issues which may be sensitive and confidential in nature. Collaborates with others acting as liaison between management and other business units. JOB DESCRIPTION: Essential Duties & Responsibilities Performs a combination of duties in accordance with departmental guidelines: Assists management in the coordination of organizational administration activities which may include but would not be limited to performance reviews, cost center updates, customer issues etc., and within scope of authority,...
CNA Chicago, IL Full Time
CNA
09/02/2026  
Underwriting Associate (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.  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...
CNA Chicago, IL Full Time
EquiTrust Life Insurance Company
09/01/2026  
Investment Accountant/Senior Investment Accountant
About Us: EquiTrust Life Insurance Company is a national carrier of competitive, client-friendly annuity products sold through a variety of distribution channels, including more than 20,000 independent agents and independent marketing organizations (IMOs). Since 2003, we have provided exceptional customer service to our clients by operating with integrity and passion. Our efforts are supported by a dedicated workforce who execute their responsibilities through teamwork and an entrepreneurial spirit. EquiTrust sells products nationwide and is headquartered in Chicago, Illinois, with operations in West Des Moines, Iowa. How You’ll Contribute: As an Investment Accountant or Senior Investment Accountant, you will support investment accounting, financial reporting, data integrity, and reconciliation activities across EquiTrust’s investment portfolio. You will work closely with the Investment Accounting team and other business partners to record and analyze investment...
EquiTrust Life Insurance Company Chicago, IL Full Time
Dual North American - Howden Group Holdings
08/29/2026  
AVP/VP Underwriting Builders Risk
At DUAL North America, our core values dictate how we live and work. We are a group with independence and people at its heart and we are a home for talent with a unique culture: the biggest small company in the world. The focus on being a People First business has always been at the very heart of the Group; Our vision was to create an independent business with a unique culture and one that would survive and thrive as a business controlled by the people working for it. And finding the most talented and entrepreneurial people to join the Group has been and will continue to be key. DUAL North America, Inc. is seeking a AVP/VP Underwriting Builders Risk Classification: Exempt/Full-time Reports to: SVP Underwriting or above Travel: Up to 30% or more Salary: $140,000.00- $200,000.00 Role overview DUAL North America is seeking an AVP/VP Underwriter for the Builders Risk division.    At DUAL, AVP/VP Underwriters play a critical leadership role in defining the...
Dual North American - Howden Group Holdings Chicago, IL Full Time
Intact Insurance Specialty Solutions
08/25/2026  
Product Development Specialist (Hybrid)
Our employees are at the heart of what we do: helping people, businesses and society prosper in good times and be resilient in bad times. When you join our team, you are bringing this purpose to life alongside a passionate community. Feel empowered to learn and grow while being valued for who you are. At Intact, we commit to supporting you in reaching your goals with tools, opportunities, and flexibility. It’s our promise to you.  Who we are At Intact Insurance Specialty Solutions, we are experts at what we do in protecting what makes businesses unique. Our deep understanding of the specialty insurance market is the foundation for our customized solutions, backed by targeted risk control and claims services. Our employees are passionate about providing insurance coverage that’s aligned to our targeted customer groups. Intact’s Global Specialty Lines business spans across more than 20 verticals in four distinct markets: U.S., Canada, UK and Europe. The following...
Intact Insurance Specialty Solutions Chicago, IL Full Time

 

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