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Chicago, IL underwriting trainee

65 underwriting trainee jobs found in Chicago, IL

Auto-Owners Insurance
01/27/2026  
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, USA Full Time
Auto-Owners Insurance
01/27/2026  
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 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 insurance coverages and contracts along with company philosophy and procedures, in order to make...
Auto-Owners Insurance Marion, IN, USA Full Time
Auto-Owners Insurance
01/27/2026  
Entry Level Personal Lines 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 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 insurance coverages and contracts along with company philosophy and procedures, in order to make...
Auto-Owners Insurance Lansing, MI, USA Full Time
Auto-Owners Insurance
03/17/2026  
Personal Lines 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 We offer a merit-based work-from-home program based on job responsibilities. After initial training in-person, this specific role could have the flexibility to work from home up to 3 days per week. 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 insurance coverages and contracts along with company philosophy and procedures, in order to make...
Auto-Owners Insurance Appleton, WI, USA Full Time
Auto-Owners Insurance
01/27/2026  
Personal Lines 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 We offer a merit-based work-from-home program based on job responsibilities. After initial training in-person, this specific role could have the flexibility to work from home up to 3 days per week. 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 insurance coverages and contracts along with company philosophy and procedures, in order to make...
Auto-Owners Insurance Appleton, WI, USA Full Time
Auto-Owners Insurance
01/27/2026  
Personal Lines 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 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 insurance coverages and contracts along with company philosophy and procedures, in order to make...
Auto-Owners Insurance Lima, OH, USA Full Time
Travelers
03/12/2026  
Underwriting Professional Development Program, Technology - June 2026
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 Chicago, IL, USA Full Time
GEICO
02/17/2026  
Auto Damage Trainee
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. Auto Damage Trainee – Chicago, IL “ *Starting pay rate varies based upon position and location. Ask your Recruiter for details!” Accidents can be scary, and our Auto Damage team rises to the occasion to provide unparalleled customer service when our customers need us the most. We’re looking for Auto Damage Trainees in Chicago, IL who are motivated and ready to grow their careers to the next level...
GEICO Chicago, IL, USA Full Time
Westfield
10/13/2025  
WSP IT Intern, Chicago Office (2026 Summer)
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.   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 Intern Program are immersed in the day-to-day operations of a fast-moving, growing insurance...
Westfield Chicago, IL, USA Full Time
Ryan Specialty
09/22/2025  
Underwriter, E&S Property
Position Summary Join Our Team of Forward-Thinking Underwriters! Are you a recent RMI graduate or an industry professional ready to take the next step in your underwriting career? Velocity is looking for driven, collaborative individuals to underwrite E&S Specialty Property Insurance: covering high-impact perils like hurricanes, earthquakes, tornadoes, and fires across the U.S. About Velocity Velocity, recently acquired by Ryan Specialty, is a cutting-edge managing general underwriter (MGU) specializing in E&S insurance for the U.S. specialty commercial property market. Innovation is at the core of everything we do. We rapidly connect risk with capital, tackling market challenges with agility and purpose. Our mission is to expand access to global capital for property and business owners, especially in underserved areas. By partnering with brokers, agents, and top-tier capital providers, we combine deep industry expertise with advanced data analytics and technology to...
Ryan Specialty Chicago, IL, USA Full Time
Reliance Matrix
03/05/2026  
Client Management Trainee Program
Job Responsibilities and Requirements Launch your career with momentum.  The STAR (Service Training and Readiness) Program at Reliance Matrix is your fast track into a dynamic, high‑impact career in Client Management . This one‑year immersive program is built for individuals who are hungry to learn, eager to grow, and ready to jump into a role where relationships, strategy, and results matter. As a STAR Associate, you’ll gain hands‑on experience, build your industry expertise, and sharpen your sales and service skills — all while collaborating with leaders who are invested in your success. You won’t just observe the business… you’ll contribute to it. Successful completion of the program propels you directly into a Client Management position , where your earning potential and career growth are truly unlimited. Program Overview From day one, you’ll be part of a high‑performing team that will challenge you, support you, and help you grow. Throughout the program,...
Reliance Matrix Schaumburg, IL, USA
Auto-Owners Insurance
01/27/2026  
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, USA Full Time
GEICO
03/09/2026  
Auto Damage Trainee
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.  Auto Damage Trainee –Kenosha/Racine, WI Salary: $30.53 per hour / $61,500 annually Accidents can be scary, and our Auto Damage team rises to the occasion to provide unparalleled customer service when our customers need us the most. We’re looking for Auto Damage Trainees in Kenosha/Racine, WI who are motivated and ready to grow their careers to the next level with GEICO. Flexibility to work in...
GEICO Kenosha, WI, USA Full Time
Auto-Owners Insurance
01/27/2026  
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 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 claims training program for the assigned line of insurance and requires the person to:...
Auto-Owners Insurance Portage, MI, USA Full Time
Auto-Owners Insurance
01/27/2026  
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 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 claims training program for the assigned line of insurance and requires the person to:...
Auto-Owners Insurance Madison, WI, USA Full Time
Auto-Owners Insurance
01/27/2026  
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, USA Full Time
GEICO
03/06/2026  
Auto Damage Trainee
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.  Auto Damage Trainee – Lafayette, Indiana Salary: $27.98 per hour / $56,375 annually ​ Accidents can be scary, and our Auto Damage team rises to the occasion to provide unparalleled customer service when our customers need us the most. We’re looking for Auto Damage Trainees in Lafayette, Indiana who are motivated and ready to grow their careers to the next level with GEICO. Flexibility to work in...
GEICO Indianapolis, IN, USA Full Time
GEICO
03/06/2026  
Auto Damage Trainee
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.  Auto Damage Trainee – Indianapolis, IN “ *Starting pay rate varies based upon position and location. Ask your Recruiter for details!” Sign on bonus: $1,500 for candidates who hold  an   adjusters license that is active and in good standing. Accidents can be scary, and our Auto Damage team rises to the occasion to provide unparalleled customer service when our customers...
GEICO Indianapolis, IN, USA Full Time
Auto-Owners Insurance
01/27/2026  
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 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 claims training program for the assigned line of insurance and requires the person to: Investigate,...
Auto-Owners Insurance Indianapolis, IN, USA Full Time
Auto-Owners Insurance
01/27/2026  
Claims Representative – Catastrophe Claims
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 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 claims training program for the assigned line of insurance and requires the person to: Investigate,...
Auto-Owners Insurance Lansing, MI, USA Full Time

 

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