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Insurance Claims Trainee Jobs in Wisconsin (NOW HIRING)

Progressive

Claims Adjuster Trainee

Pewaukee, WI · Hybrid

$54K - $57K/yr

As a claims adjuster trainee , you'll learn how to help customers get back on the road after an ... We'll also teach you the insurance stuff - providing in-depth training on property damage and ...

Progressive

Claims Adjuster Trainee

Milwaukee, WI · Hybrid

$54K - $57K/yr

As a claims adjuster trainee , you'll learn how to help customers get back on the road after an ... We'll also teach you the insurance stuff - providing in-depth training on property damage and ...

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Insurance Claims Trainee information

What types of training and mentorship can I expect as an insurance claims trainee?

As an Insurance Claims Trainee, you can expect a blend of classroom-based learning and on-the-job training. You’ll likely participate in structured development programs led by senior adjusters and trainers, covering topics such as policy interpretation, claims investigation, negotiation, and customer service. Mentorship is a key part of most programs, with experienced claims professionals providing guidance, feedback, and support as you handle real claims under supervision. This setup allows you to gain practical experience while gradually increasing your responsibility and independence.

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

To thrive as an Insurance Claims Trainee, you need a bachelor's degree (often in business or a related field), analytical skills, and basic knowledge of insurance principles. Familiarity with claims management software, Microsoft Office Suite, and sometimes completion of industry certifications such as AIC (Associate in Claims) is typical. Attention to detail, effective communication, and strong problem-solving abilities are important soft skills for this role. These skills and qualifications help ensure accurate claims processing, customer satisfaction, and compliance with regulatory standards.

What is the difference between Insurance Claims Trainee vs Insurance Claims Adjuster?

AspectInsurance Claims TraineeInsurance Claims Adjuster
Required CredentialsHigh school diploma or equivalent; some roles may prefer certificationsHigh school diploma; often requires licensing and certifications
Work EnvironmentTraining programs, office settings, supervised tasksFieldwork, office, or a combination; independent decision-making
Employer & Industry UsageEntry-level training within insurance companiesFull-time professional role handling claims processing and settlement

The main difference is that an Insurance Claims Trainee is an entry-level position focused on learning and training, while an Insurance Claims Adjuster is a fully qualified professional responsible for evaluating and settling claims. Trainees typically undergo training and supervision, whereas Adjusters work independently with licensing and experience.

What does an insurance claims trainee do?

An Insurance Claims Trainee learns how to evaluate and process insurance claims under the supervision of experienced claims adjusters or managers. They are trained to investigate claims, assess damages, review policy coverage, and communicate with policyholders and third parties. This role involves both classroom and on-the-job training to understand insurance policies, legal requirements, and best practices in claims handling. As trainees gain experience, they gradually take on more responsibility and work towards becoming fully qualified claims adjusters.
What are the most commonly searched types of Insurance Claims jobs in Wisconsin? The most popular types of Insurance Claims jobs in Wisconsin are:
What are popular job titles related to Insurance Claims Trainee jobs in Wisconsin? For Insurance Claims Trainee jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Insurance Claims Trainee jobs in Wisconsin look for? The top searched job categories for Insurance Claims Trainee jobs in Wisconsin are:
What cities in Wisconsin are hiring for Insurance Claims Trainee jobs? Cities in Wisconsin with the most Insurance Claims Trainee job openings:
Insurance Claims Trainee jobs near you
Infographic showing various Insurance Claims Trainee job openings in Wisconsin as of July 2026, with employment types broken down into 1% As Needed, 73% Full Time, 22% Part Time, and 4% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution.

Claims Adjuster Trainee

Progressive

Pewaukee, WI • Hybrid

$54K - $57K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 7 days ago

Progressive Insurance rating

8.6

Company rating: 8.6 out of 10

Based on 595 frontline employees who took The Breakroom Quiz

88th of 303 rated insurance

Job description

Progressive is dedicated to helping employees move forward and live fully in their careers. Your journey has already begun. Apply today and take the first step to Destination: Progress.

As a claims adjuster trainee, you’ll learn how to help customers get back on the road after an accident. This is not a field position, which means you’ll be building relationships with customers over the phone. In a fast-paced environment, you’ll learn how to resolve a full case load of claims efficiently while managing the claims process from start to finish. You’ll have the support of a collaborative team and ongoing coaching from leaders. We’ll also teach you the insurance stuff – providing in-depth training on property damage and insurance contracts so you can confidently and independently adjust claims.

This is a hybrid role, which means you’ll work in-office two days that are selected by local leadership and choose where you want to work the other three days, whether that’s at home or in the office, for a period of 12 months. After that period, the days you’ll be expected to report to an office for important meetings, training, and collaboration will vary based on business need. In this hybrid work environment, you’ll be supported by your leaders and tenured colleagues to develop relationships, establish connections, and share practices that are important to your development. If you prefer an in-office environment, you’re welcome to work in the office as often as you would like.

Duties & responsibilities (upon completion of training)

  • Determine coverage
  • Determine liability (who’s at fault for the damages)
  • Interview customers, claimants, and witnesses
  • Partner with appraisers/estimators to manage vehicle repairs
  • Negotiate with customers and other insurance carriers and resolve claims

Minimum qualifications

  • Three years of work experience OR
  • Bachelor’s degree OR
  • Two years work experience and an associate degree

Schedule: Monday - Friday, 8:30 am - 5:30 pm for the first four weeks during training, then 9:00 am - 6:00 pm.

Location: 9000 W Chester St, Ste 215, Milwaukee, WI 53214

Compensation

  • Once you complete training and pass any necessary testing requirements, your salary will be $54,000-$57,500/year, however, during training, you’ll be paid hourly based on your annual salary.
  • Gainshare annual cash incentive payment up to 16% of your eligible earnings based on company performance

Benefits

  • 401(k) with dollar-for-dollar company match up to 6%
  • Medical, dental & vision, including free preventative care
  • Wellness & mental health programs
  • Health care flexible spending accounts, health savings accounts, & life insurance
  • Paid time off, including volunteer time off
  • Paid & unpaid sick leave where applicable, as well as short & long-term disability
  • Parental & family leave; military leave & pay
  • Diverse, inclusive & welcoming culture with Employee Resource Groups
  • Career development & tuition assistance

Energage recognizes Progressive as a 2026 Top Workplace for: Innovation, Purposes & Values, Work-Life Flexibility, Compensation & Benefits, and Leadership.

Equal Opportunity Employer

Applicants must be authorized to work for any employer in the U.S. without the need or potential need, of current or future sponsorship for employment. Progressive does not hire candidates with (e.g., F-1 CPT, OPT, or STEM OPT, H-1B, O-1, E-3, TN) statuses for this role.

For ideas about how you might be able to protect yourself from job scams, visit our scam-awareness page at https://www.progressive.com/careers/how-we-hire/faq/job-scams/

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