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Insurance Underwriter Trainee Jobs in Wisconsin (NOW HIRING)

UFG Insurance

WI · On-site

$70 - $110/hr

Provide training, direction, and assistance to associate underwriters and underwriter trainees. Job Specifications: Education: * Bachelor's degree, or combination of education and surety experience

New

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 ...

MGIC

Senior Customer Trainer

Milwaukee, WI · On-site

$87.99 - $149.59/hr

Monitor and evaluate trainees' progress during training and ensure competence in applying newly ... insurance, mortgage lending, underwriting, or related financial services environments. * Current ...

New

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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 Sep 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.

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 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 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.

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 emphasize a willingness to learn and basic computer skills over extensive experience.

Is insurance underwriting hard to get into?

Insurance underwriting can be competitive, especially for entry-level trainee positions, as they often require strong analytical skills, attention to detail, and sometimes a relevant degree or certification. Gaining experience through internships or related coursework can improve chances, but the job typically involves learning industry-specific tools and regulations. Overall, it requires dedication and a willingness to develop specialized knowledge.

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 August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 20% Part Time, and 5% Contract. Highlights an 84% Physical, 1% Hybrid, and 15% Remote job distribution, with an average salary of $79,616 per year, or $38.3 per hour.

Surety Underwriter

UFG Insurance

WI • On-site

$70 - $110/hr

Other

Posted 3 days ago

New

Job description

UFG is hiring for a Surety Underwriter who will actively working towards building and maintaining a profitable mix of new and existing surety business by developing and maintaining strong working relationships with the agency force. Demonstrate strong analytical skills to evaluate risks for acceptability within their authority and company underwriting parameters. Make regular agency visits and calls to assess growth and profitability of agents in their territory. Prospect and appoint new quality agents in the territory. Visit current and potential contractor’s place of business to better assess acceptability and quality of the accounts.

**The ideal candidate will reside in the Dallas, Houston or Austin Texas territory**

Essential Duties and Responsibilities:
  • Underwrite new submissions and existing accounts utilizing authority granted by head of Surety and with assistance from mentors. Evaluate and assess financial status, credit standing, and organization profile to analyze and determine acceptability of the risk within framework of UFG underwriting policies and procedures.
  • Develop and maintain strong relationships with agents/brokers.
  • Oversee a book of contract surety business within defined territory. Meet production, marketing, and profitability goals and develop marketing plan using the territory management tool.
  • Upload and update file information electronically and purge obsolete data per department guidelines.
  • Handles all confidential information with discretion.
  • Provide high quality customer service in all interactions with internal and external customers.
  • Request underwriting information from agencies. Review and process information received.
  • Perform annual review of accounts including financial analysis, obtaining current bank line of credit letters, preparing profiles, and recommendation of line of authority.
  • Instruct, assign and review work completed by support staff.
  • Create record of communications concerning activities per department standards.
  • Provide training, direction, and assistance to associate underwriters and underwriter trainees.
Job Specifications: Education:
  • Bachelor’s degree, or combination of education and surety experience
  • Bachelor’s degree in business administration, economics, finance or accounting preferred
Certifications/Designations:
  • Certified, or working towards, AFSB designation.
  • Must have a valid and current drivers’ license and must have acceptable driving record in accordance with Company practice.
  • Employees are expected to participate in continuing education throughout their careers.
Experience:
  • 3+ years of contract surety underwriting experience.
Working Conditions:
  • General office environment.
  • Up to 25% of travel is required, to visit agency force and contract accounts either independently or by accompanying surety representatives. Overnight trips included.
  • May be exposed to weather conditions, and/or results and debris of adverse weather conditions, during agency/contract visits.

Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws.For further information, please review the Know Your Rights notice from the Department of Labor.

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