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Insurance Apprentice Jobs in Chicago, IL (NOW HIRING)

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Insurance Apprentice information

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How much do insurance apprentice jobs pay per hour?

As of Aug 13, 2026, the average hourly pay for insurance apprentice in Chicago, IL is $22.69, according to ZipRecruiter salary data. Most workers in this role earn between $17.84 and $24.76 per hour, depending on experience, location, and employer.

What is an insurance apprentice?

Insurance Apprentices are entry-level professionals who learn about the insurance industry while working under the guidance of experienced mentors. They typically participate in a structured program that combines on-the-job training with classroom learning, gaining knowledge about various insurance products, policies, regulations, and customer service. The apprenticeship helps individuals develop both technical and soft skills needed for a career in insurance, and often leads to a permanent position upon successful completion.

What are the key skills and qualifications needed to thrive as an insurance apprentice, and why are they important?

To thrive as an Insurance Apprentice, you should have a solid grasp of basic mathematics, attention to detail, and an eagerness to learn about insurance principles, often supported by a high school diploma or equivalent. Familiarity with office software, customer relationship management (CRM) systems, and sometimes basic insurance certification courses are valuable. Strong communication, problem-solving abilities, and a proactive attitude help apprentices build relationships and adapt quickly in the workplace. These skills are essential for accurately handling client information, supporting experienced staff, and developing a successful insurance career.

What types of projects or assignments can an insurance apprentice expect to handle during their training period?

As an Insurance Apprentice, you can expect to be involved in a variety of hands-on assignments such as processing policy applications, assisting with claims investigation, and supporting customer service inquiries. You'll often shadow experienced agents and underwriters to learn about risk assessment and policy quoting. Apprentices also participate in administrative tasks and may help prepare client presentations or reports, providing a broad overview of the insurance business. This practical exposure is designed to build your confidence and understanding of the industry's workflows before taking on more responsibility.

What is the difference between Insurance Apprentice vs Insurance Agent?

AspectInsurance ApprenticeInsurance Agent
Required CredentialsTypically no formal licensing initially; may need to obtain licenses laterMust be licensed in the state to sell insurance
Work EnvironmentTraining programs, office settings, or on-the-job learningClient-facing, sales-focused, often in offices or client locations
Employer & Industry UsageEntry-level role within insurance companies or agenciesLicensed professionals working independently or for agencies
Search & Comparison IntentLearning role, entry-level position, trainingSales, licensing, client interaction

The main difference is that an Insurance Apprentice is an entry-level trainee often in training, while an Insurance Agent is a licensed professional actively selling insurance products. Apprentices typically focus on learning and gaining experience, whereas agents handle client interactions and sales after obtaining necessary licenses.

How to get a job in insurance apprentice with no experience?

To become an insurance apprentice with no experience, focus on developing basic knowledge of insurance principles, customer service skills, and attention to detail. Many programs accept candidates with a high school diploma and provide on-the-job training, so applying to entry-level positions or internships can help you gain relevant experience and certifications such as the Property and Casualty license.
What are the most commonly searched types of Insurance jobs in Chicago, IL? The most popular types of Insurance jobs in Chicago, IL are:
Infographic showing various Insurance Apprentice job openings in Chicago, IL as of June 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $47,187 per year, or $22.7 per hour.

Executive Underwriter or AVP Underwriting Director- Middle Market

Zurich Insurance Company Ltd.

Chicago, IL โ€ข On-site

$110K - $238K/yr

Full-time

Posted 16 days ago


Job description

Over the past five years, Zurich North America has built a world-class Middle Market operation that serves key industries across the U.S. We strive to assemble a team of dedicated Middle Market leaders and underwriters who understand this space very deeply and who grasp the unique challenges of the various industry segments and the individual customers we serve. We are looking to add to our team in Chicago, IL.

While this position is based out of the Chicago office, you will have the flexibility to work on a hybrid basis. You will partner with your manager to set a flexible work schedule that supports you, our customers, and our brokers and agents.

In this role, you will serve as a customer advocate with a focus on improving customer experience by understanding their unique risks and offering the best end-to-end solution for their Property & Casualty insurance needs.

What you can expect in a Market Facing, Middle Market Underwriting position at Zurich:

  • You will develop and maintain relationships with broker partners and customers across all industries in support of business objectives.
  • You will leverage your Property and Casualty underwriting acumen across risk assessment, exposure evaluation and pricing to generate and maintain a profitable book of new and renewal business.
  • You will work collaboratively across business units including but not limited to; claims, finance, risk engineering, actuary, and technical underwriting while gaining extensive knowledge in a growing and innovative industry. 
  • You will be empowered to use your technical underwriting, negotiation and interpersonal skills to grow and develop relationships with preferred distribution partners in an assigned territory.

This role will be filled at either the Executive Underwriter or AVP Underwriting Director level. The hiring manager will determine the appropriate level based upon the selected applicantโ€™s experience and skill set relative to the qualifications listed for this position. 

Executive Underwriter Required Qualifications:

  • High School Diploma or Equivalent and 5 or more years of experience in the Underwriting or Market Facing area.
    OR
  • High School Diploma or Equivalent and 10 or more years of experience in the Claims or Underwriting Support area
    OR
  • Zurich Certified Insurance Apprentice including an Associate Degree and 3 or more years of experience in the Underwriting or Market Facing area
    OR
  • Zurich Certified Insurance Apprentice including an Associate Degree and 8 or more years of experience in the Claims or Underwriting Support are
    AND
  • Knowledge of Microsoft Office
  • Experience working on time restraints for quotes on new and renewal business
  • Experience working in a team environment

OR

 AVP, Underwriting Director Required Qualifications:

  • High School Diploma or Equivalent and 7 or more years of experience in the Underwriting or Market Facing area
    OR
  • High School Diploma or Equivalent and 14 or more years of experience in the Claims or Underwriting Support area
    OR
  • Zurich Certified Insurance Apprentice including an Associate Degree and 5 or more years of experience in the Underwriting or Market Facing area
    OR
  • Zurich Certified Insurance Apprentice including an Associate Degree and 12 or more years of experience in the Claims or Underwriting Support area

Preferred Qualifications: 

  • Bachelors Degree
  • Experience handling all lines of business in the Middle Market space (Auto, GL, Workers Compensation, Umbrella, Inland Marine and Property)
  • Broker relationships in the Chicago Market
  • Strong verbal and written communication skills
  • Microsoft Office proficiency

Your pay at Zurich is based on your role, location, skills, and experience. We follow local laws to ensure fair compensation. You may also be eligible for bonuses and merit increases. If your expectations are above the listed range, we still encourage you to applyโ€”your unique background matters to us. The combined salary range for this position is $110,200.00 - $238,700.00. The proposed salary range for the Executive Underwriter is $110,200.00 - $180,500.00, with short-term incentive bonus eligibility set at 15%. The proposed salary range for the AVP Underwriting Director is $145,800.00 - $238,700.00, with short-term incentive bonus eligibility set at 20%.โ€ฏ

We offer competitive pay and comprehensive benefits for employees and their families. [Learn more about Total Rewards here.]

 

Why Zurich?

At Zurich, we value your ideas and experience. We offer growth, inclusion, and a supportive environmentโ€”so you can help shape the future of insurance. Zurich North America is a leader in risk management, with over 150 years of expertise and coverage across 25+ industries, including 90% of the Fortune 500ยฎ.

Join us for a brighter futureโ€”for yourself and our customers.

Zurich in North America does not discriminate based on race, ethnicity, color, religion, national origin, sex, gender expression, gender identity, genetic information, age, disability, protected veteran status, marital status, sexual orientation, pregnancy or other characteristics protected by applicable law. Equal Opportunity Employer disability/vets.

Zurich complies with 18 U.S. Code ยง 1033.

 

Please note: Zurich does not accept unsolicited CVs from agencies. Preferred vendors should use our Recruiting Agency Portal.

Location(s): AM - Chicago
Remote Working: Hybrid
Schedule: Full Time
Employment Sponsorship Offered: No  
 
Linkedin Recruiter Tag: #LI-AK1 LI-ASSOCIATE #LI-HYBRID