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Insurance Underwriter Trainee Jobs in Wisconsin (NOW HIRING)

Mgic Investment

Senior Customer Trainer

Milwaukee, WI · On-site

$87K - $149K/yr

Monitors and evaluates trainees' progress during training and ensures trainees are competent to ... insurance, mortgage lending, underwriting, or related financial services environments. * Current ...

Auto-Owners Insurance

Claims Representative

Madison, WI · On-site

Auto-Owners Insurance, a top-rated insurance carrier, is seeking a motivated claims trainee to join ... Company's underwriting guidelines for coverage * Continually develop product knowledge through ...

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Insurance Underwriter Trainee information

See Wisconsin salary details

$32.8K

$79.6K

$140.8K

How much do insurance underwriter trainee jobs pay per year?

As of Aug 4, 2026, the average yearly pay for insurance underwriter trainee in Wisconsin is $79,616.00, according to ZipRecruiter salary data. Most workers in this role earn between $61,600.00 and $87,800.00 per year, depending on experience, location, and employer.

Can you get a job as an insurance underwriter trainee with no experience?

Insurance underwriter trainee positions often accept candidates with little or no prior experience, focusing instead on relevant skills such as attention to detail, analytical ability, and strong communication. Employers may provide on-the-job training and may require a related degree or certification, such as an insurance license or coursework in risk management. Entry-level roles typically involve learning underwriting processes and industry standards through training programs.

What are the key skills and qualifications needed to thrive in the insurance underwriter trainee position, and why are they important?

To excel as an Insurance Underwriter Trainee, strong analytical abilities, attention to detail, and a bachelor’s degree in finance, business, or a related field are typically required. Familiarity with underwriting software and risk assessment tools, as well as proficiency in Microsoft Office Suite, is highly valuable. Effective communication, teamwork, and eagerness to learn help candidates build relationships and adapt to changing guidelines. These skills are vital for making accurate risk decisions, supporting team objectives, and ensuring compliance with industry standards.

What does the typical career path look like for an insurance underwriter trainee?

As an Insurance Underwriter Trainee, you will begin by learning the fundamentals of risk assessment, policy evaluation, and company underwriting guidelines under the supervision of experienced underwriters. Over time, trainees take on greater responsibilities, such as reviewing applications, making independent recommendations, and interacting more directly with agents and clients. Many trainees advance to Underwriter roles within one to two years, with opportunities for further specialization or progression into senior underwriter or management positions. Career growth often depends on performance, continued education, and acquiring professional certifications such as the Chartered Property Casualty Underwriter (CPCU) designation.

What is an insurance underwriter trainee?

An Insurance Underwriter Trainee is an entry-level position where individuals learn how to assess risks and determine appropriate insurance coverage, terms, and premiums. Trainees undergo structured training, including coursework and hands-on experience, to understand underwriting guidelines and company policies. They work closely with senior underwriters to evaluate applications, analyze data, and make informed decisions. This role is ideal for those with strong analytical skills and attention to detail who are interested in a career in the insurance industry.

What are the most commonly searched types of Insurance Underwriter jobs in Wisconsin? The most popular types of Insurance Underwriter jobs in Wisconsin are:
What are popular job titles related to Insurance Underwriter Trainee jobs in Wisconsin? For Insurance Underwriter Trainee jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Insurance Underwriter Trainee jobs in Wisconsin look for? The top searched job categories for Insurance Underwriter Trainee jobs in Wisconsin are:
Insurance Underwriter Trainee jobs near you
Infographic showing various Insurance Underwriter Trainee job openings in Wisconsin as of July 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $79,616 per year, or $38.3 per hour.

Trainee - Customer Service Representative (Crivitz, WI)

Robertson Ryan Insurance

Crivitz, WI • On-site

$14.25 - $19.50/hr

Full-time, Part-time

Re-posted 17 days ago

Robertson Ryan Insurance rating

8.7

Company rating: 8.7 out of 10

Based on 7 frontline employees who took The Breakroom Quiz

70th of 301 rated insurance

Job description

Recognized nationally as a Top Workplace and Top 100 US Insurance Agency!

Since 1960, Robertson Ryan Insurance has provided comprehensive solutions across Business, Benefits, and Personal Insurance. We proudly serve over 70,000 clients, from small businesses to major national accounts across various industries. With a team of more than 526 professionals and partnerships with over 150 insurance companies, we are the 44th largest Property amp; Casualty Insurance Agency according to the Insurance Journal. Our dynamic and enjoyable culture is a cornerstone of our success, with many team members having been with us for over a decade. It’s an exciting time to join our growing firm!

Customer Service Representative (Trainee):

As a Customer Service Representative in Commercial or Personal Lines, you will have the primary responsibility of managing customers' service needs. In this role, you will work with the account manager, prepare proposals, answer incoming phone calls, greet and direct insurance office visitors, enter change requests and endorsements, and maintain our agency management system with current information.

This is an onsite position in our Crivitz, WI office.
This role is a great opportunity for someone eager to learn, develop new skills, and grow within the organization. In addition to front desk and administrative responsibilities, the position offers exposure to the insurance business and opportunities for professional development and advancement over time.

Responsibilities of a CSR (Trainee):

  • Commercial and Personal Lines policy information collection
  • Distribute quotes to prospective customers and current customers with follow up to answer questions.
  • Maintain document retention and document uploads, as needed per carriers.
  • Assist clients with making coverage changes and complete all service requests for clients.
  • Provide billing support to customers.
  • Understand and discuss coverages with clients.
  • Develop good working relationships with the underwriters.
  • Ensure that client issues are efficiently handled with resolution.
  • Email personal policy documents, as needed.
  • Answer office phone, assist customer thoroughly and direct call to appropriate person, if needed.
  • Establish and preserve a solid business rapport with clients.
  • Maintain accuracy in agency management system, quoting system, and carrier systems.
  • Additional office projects, as needed.

Required Qualifications (within 6 months of hire):

  • Willing to train the right candidate with excellent customer service and must be willing to get a Property amp; Casualty Insurance License within 6 months of hire.
  • Must be willing to work full or part-time in office at our Crivitz, WI location.

Requirements of a CSR (Trainee):

  • Ability to operate various computer programs (Microsoft Office Suite, Google Suite, etc.)
  • Demonstrate excellent oral and written communication skills.
  • Excellent organizational skills and strong problem-solving skills.
  • Ability to prioritize and handle multiple tasks independently.
  • Exceptional customer service experience and skills.

EEO/AA Statement: Robertson Ryan provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Attention to all Recruiting Agencies: Recruitment at RRI works on a direct sourcing model. We will contact agencies directly if needed. RRI is not responsible for any related fees for resumes submitted to job postings, our employees or any other part of our company.

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