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Underwriter Trainee Jobs in Wisconsin (NOW HIRING)

WI ยท On-site

$100 - $152/hr

As a Large Accounts Underwriter, you'll manage a defined territory and drive profitable growth by evaluating complex commercial risks, developing tailored coverage solutions, and making strategic ...

New

Bilingual Underwriter

Stevens Point, WI ยท On-site

$75K - $82K/yr

Wholesure, division of Acrisure, is looking for an Underwriter. This role will work directly with multiple of our carrier partners to shop, approve the risk, and underwrite new and renewal policies.

WI ยท On-site

$90 - $140/hr

Overview The Senior Underwriter administers the underwriting agencies within their assigned territory. Completes work in compliance with company underwriting, authority, and pricing standards.

Senior Underwriter

Madison, WI ยท On-site +1

$99K - $117K/yr

Are you an underwriting professional who thrives in high-stakes, transformative environments? Do you find satisfaction in mitigating risk, identifying opportunities, and shaping the course of a ...

Senior Stop Loss Underwriter

Stevens Point, WI ยท On-site +1

$90K - $125K/yr

The Senior Stop Loss Underwriter is responsible for evaluating, pricing, and managing risk for employer-sponsored self-funded health plans. This role includes underwriting both new business and ...

Showing results 21-40

Underwriter Trainee information

See Wisconsin salary details

$32.8K

$79.6K

$140.8K

How much do underwriter trainee jobs pay per year?

As of Sep 4, 2026, the average yearly pay for 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 underwriter trainee?

An Underwriter Trainee is an entry-level professional who learns how to evaluate risks and determine appropriate insurance coverage and premiums under the supervision of experienced underwriters. Their training involves learning about insurance policies, analyzing applications, assessing potential risks, and making recommendations based on company guidelines. This role serves as a starting point for a career in underwriting, providing foundational knowledge and practical experience in the insurance industry.

What are the key skills and qualifications needed to thrive as an underwriter trainee?

To thrive as an Underwriter Trainee, you need strong analytical abilities, 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 Excel are commonly required, and industry certifications like CPCU can be advantageous. Excellent communication, problem-solving, and organizational skills help you collaborate with stakeholders and manage multiple priorities. These skills are essential to accurately assess risk, make informed decisions, and contribute to the overall profitability and integrity of the insurance company.

What are some typical challenges an underwriter trainee might encounter during their first year on the job?

As an Underwriter Trainee, one common challenge is learning to balance risk assessment with client needs, while adhering to company policies and regulatory requirements. Trainees often need to quickly develop a strong understanding of underwriting guidelines and how to apply them to real-world cases, which can be complex and varied. Additionally, adapting to a fast-paced environment and effectively collaborating with senior underwriters, brokers, and agents requires strong communication and organizational skills. Overcoming these challenges is an important part of gaining confidence and proficiency in the role.

What is the difference between Underwriter Trainee vs Underwriter?

AspectUnderwriter TraineeUnderwriter
Required CredentialsBachelor's degree, training programsExperience, certifications like CPCU or ARM often preferred
Work EnvironmentTraining programs, supervised tasksIndependent decision-making, client interaction
Employer & Industry UsageInsurance companies, entry-level rolesInsurance companies, experienced roles
Search & Comparison IntentLearning about entry-level underwriting rolesUnderstanding experienced underwriting positions

The main difference between an Underwriter Trainee and an Underwriter is experience level. Trainees are in training, focusing on learning the basics, while Underwriters have gained experience and handle complex risk assessments independently.

How do you become an underwriter trainee with no experience?

To become an underwriter trainee with no experience, candidates typically need a bachelor's degree in fields like finance, business, or economics. Entry-level roles often require strong analytical skills, attention to detail, and proficiency with computer software such as Excel; some companies may also offer training programs or on-the-job learning to develop underwriting skills.

How much do beginner underwriter trainees make?

Beginner underwriter trainees typically earn between $40,000 and $55,000 annually, depending on the industry, location, and company. Entry-level roles often include training on underwriting software and risk assessment, with salaries increasing as skills and experience grow.

What do underwriter trainees do?

Underwriter trainees assist in evaluating insurance applications by reviewing risk factors, analyzing data, and determining policy eligibility. They learn to use underwriting guidelines and may work under the supervision of experienced underwriters to develop their skills in assessing risk and making coverage decisions.

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

The most popular types of Underwriter jobs in Wisconsin are:

What cities in Wisconsin are hiring for Underwriter Trainee jobs?

Cities in Wisconsin with the most Underwriter Trainee job openings:

Infographic showing various Underwriter Trainee job openings in Wisconsin as of August 2026, with employment types broken down into 88% Full Time, and 12% Part Time. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $79,616 per year, or $38.3 per hour.

Specialty Underwriter

Michigan Millers Mutual Insurance Company

Middleton, WI โ€ข On-site

$63K - $86K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 3 days ago

New


Job description

Description:

Who are we?

Specialty Insurance Solutions (SIS) is a member of Michigan Millers Mutual Insurance Company. Michigan Millers Mutual Insurance Company is a mutual insurance company and an affiliate of Western National Mutual Insurance, it is rated A (Excellent) by A.M. Best, with over 140 years of experience serving policyholders’ property and casualty insurance needs across multiple regions in the United States. Michigan Millers believes in striving for growth without sacrifice. We know that our culture creates and cultivates happy and dedicated employees, which we believe gives us the ability to deliver the highest level of customer service.


The core values for Michigan Millers and Western National Insurance, Connectiveness – Accountability – Empowerment are incorporated into all that we do. Our workplace culture encourages employees to seek out learning opportunities and to strive for growth and development in the insurance industry.


We understand the importance of a positive work community and a healthy workplace environment when striving for organizational success. Our emphasis on internal growth and maintaining healthy team relationships translates into external growth and building sustainable customer relationships.


Does this opportunity interest you?

Specialty Insurance Solutions is seeking an Underwriter to join our team!


The individual in this role will have the opportunity to develop and manage a book of commercial lines business through assigned agencies while building strong agency relationships and supporting established growth and profitability goals.


What are the responsibilities and opportunities of this role? 

  • Develops and manages a book of commercial lines business with assigned agencies.
  • Reviews, classifies, evaluates, and prices business within established underwriting authority.
  • Manages an assigned agency territory to achieve established growth and profitability goals.
  • Builds and maintains strong agency relationships.
  • Applies knowledge of rating methodology and coverages to underwriting decisions.
  • Travels to assigned agencies to promote products, strengthen agency partnerships, and support agency relationships.
  • Maintains an understanding of the insurance marketplace, including different lines of insurance and emerging industry issues.
  • Applies established practices, processes, procedures, and underwriting authority to analyze operations and exposures for different types of risks and write, renew, and modify business.
  • Uses research and analysis to develop practical underwriting solutions that align with organizational objectives.
  • Assesses risk and exposure on new and existing business to identify opportunities to support assigned territory loss ratio and growth objectives.
  • Achieves business goals through new business growth, renewal retention, and overall profitability for assigned agencies.
  • Identifies and analyzes medium-complexity accounts and makes sound underwriting decisions.
  • Makes recommendations to a Senior Underwriter when established authority levels are exceeded.
  • Makes decisions independently within assigned authority and executes established policies and procedures.
  • Applies knowledge to solve problems of medium scope and complexity and recommends solutions when matters fall outside assigned authority.
  • Builds customer satisfaction by setting appropriate expectations, taking responsibility for resolving customer issues, and ensuring commitments are met.
  • Performs special projects and other duties as assigned.
Requirements:

What is a must-have?

  • Strong understanding of industry practices, standards, and underwriting concepts.
  • Ability to multitask and solve problems.
  • Proficient oral and written communication skills.
  • Valid and unrestricted driver’s license with an acceptable driving record.
  • Bachelor’s degree in insurance or finance; relevant experience may be considered in lieu of a degree.
  • Proficient use of various core systems, office and computer equipment, and software packages.
  • Ability to travel up to 10% of the time.

What will our ideal candidate have?

  • Progress toward a CPCU, AU, or CIC designation.

Compensation overview

The targeted hiring range for this role is $63,000 - $86,000 annually. However, the base pay offered may vary depending on the job-related knowledge, skills, credentials, and experience of each candidate as well as other factors such as the scope and location of the role. Candidates looking for compensation outside of the posted range are encouraged to apply and will be considered based on their individual qualifications and/or may be considered for other positions.


Culture and Total Rewards

We offer full-time employees a significant Total Rewards Package, including:

  • Medical insurance options and other standard employee benefits, including dental insurance, vision benefits, life insurance, and more!
  • Health Savings Accounts (HSA) and Flexible Spending Accounts (FSA)
  • 401(k) Plan (plus company match)
  • Time Off - including vacation, volunteer, and holiday pay
  • Paid Parental Leave
  • Bonus opportunities
  • Tuition assistance
  • Wellness Program - including an onsite fitness studio

Michigan Millers and Western National Insurance believes in supporting the balance between work and life by providing a flexible work environment, which includes a variety of hybrid work arrangements designed to balance individual, job, department, and company needs. 


Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.


Michigan Millers 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.