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Underwriting Trainee Jobs in Wisconsin (NOW HIRING)

Mgic Investment

Senior Customer Trainer

Milwaukee, WI · On-site

$87K - $149K/yr

Translates industry changes, underwriting trends, and investor requirements into practical learning ... Monitors and evaluates trainees' progress during training and ensures trainees are competent to ...

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All JobsUnderwriting JobsUnderwriting Trainee JobsUnderwriting Trainee Jobs in Wisconsin

Underwriting Trainee information

See Wisconsin salary details

$32.8K

$79.6K

$140.8K

How much do underwriting trainee jobs pay per year?

As of Aug 14, 2026, the average yearly pay for underwriting 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.

What do underwriting trainees do?

Underwriting trainees assist in evaluating insurance applications by reviewing applicant information, assessing risks, and determining coverage eligibility. They learn to analyze data, use underwriting software, and develop decision-making skills under supervision, often working in an office environment with ongoing training.

What is the difference between Underwriting Trainee vs Underwriter?

AspectUnderwriting TraineeUnderwriter
CredentialsTypically entry-level, may require a degree in finance, insurance, or related fieldProfessional certification often preferred, such as CPCU or similar
Work EnvironmentTraining programs, supervised tasks, learning-focusedDecision-making, risk assessment, independent or team-based
Job ResponsibilitiesAssisting in risk evaluation, learning underwriting processesEvaluating risks, approving or rejecting policies

In summary, an Underwriting Trainee is an entry-level role focused on learning and supporting underwriting tasks, while an Underwriter is a fully responsible professional making risk decisions independently.

How much do beginner underwriting trainees make?

Entry-level underwriting trainees typically earn between $40,000 and $55,000 annually, depending on the industry, location, and company size. Starting salaries may increase with relevant skills, certifications, and experience in risk assessment and insurance policies.

What is an underwriting trainee?

Underwriting Trainees are entry-level professionals who are learning how to evaluate insurance applications, assess risks, and determine appropriate coverage and premiums. They work under the supervision of experienced underwriters and receive training in company policies, industry regulations, and risk assessment techniques. The goal of an underwriting trainee is to develop the skills necessary to make sound decisions regarding accepting or rejecting insurance applications and to eventually become a fully qualified underwriter.

What kind of training and mentorship can an underwriting trainee expect during their first year?

As an Underwriting Trainee, you can expect a structured onboarding process that combines classroom learning with hands-on experience. Most insurance companies pair trainees with experienced underwriters or mentors who provide guidance on risk assessment, policy review, and client interactions. You’ll likely rotate through different insurance lines to gain a broad understanding of underwriting practices, and participate in team meetings to discuss real cases. This collaborative environment helps you build technical skills and professional networks, laying a solid foundation for advancement within the company.

How do you become an underwriting trainee?

To become an underwriting trainee, candidates typically need a bachelor's degree in finance, economics, or a related field. Relevant skills include analytical thinking and attention to detail, and some companies may require or prefer prior internship experience in insurance or finance. On-the-job training is provided, and strong communication skills are beneficial.

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

To thrive as an Underwriting Trainee, you need strong analytical skills, attention to detail, and a bachelor's degree in finance, business, or a related field. Familiarity with underwriting software, risk assessment tools, and proficiency in Microsoft Excel are typically required, and some employers may value progress toward professional certifications like CPCU. Effective communication, organization, and a willingness to learn help candidates stand out in this entry-level position. These skills and qualities are essential for accurately assessing risks, managing data, and building a successful foundation for a career in insurance underwriting.

What are the most commonly searched types of Underwriting jobs in Wisconsin?

The most popular types of Underwriting jobs in Wisconsin are:

What are popular job titles related to Underwriting Trainee jobs in Wisconsin?

For Underwriting Trainee jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Underwriting Trainee jobs in Wisconsin look for?

The top searched job categories for Underwriting Trainee jobs in Wisconsin are:

What cities in Wisconsin are hiring for Underwriting Trainee jobs?

Cities in Wisconsin with the most Underwriting Trainee job openings:

Underwriting Trainee jobs near you
Infographic showing various Underwriting Trainee job openings in Wisconsin as of August 2026, with employment types broken down into 75% Full Time, and 25% Part Time. Highlights an 75% In-person, and 25% Hybrid job distribution, with an average salary of $79,616 per year, or $38.3 per hour.

Trainee - Customer Service Representative (Hartford, WI)

Robertson Ryan and Associates, Inc.

Hartford, WI • On-site

$17.50 - $23.75/hr

Full-time, Part-time

Posted 7 days ago

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 & 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 Hartford, WI office. This position is Monday-Friday from 8:00am-4:30pm.
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 & Casualty Insurance License within 6 months of hire.
  • Must be willing to work full or part-time in office at our Hartford, 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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