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Underwriting Trainee Program Jobs in Wisconsin (NOW HIRING)

As training progresses, performs basic underwriting duties on non-complex and complex accounts ... Additionally, you may be eligible to participate in our annual incentive program, depending on your ...

As training progresses, performs basic underwriting duties on non-complex and complex accounts ... Additionally, you may be eligible to participate in our annual incentive program, depending on your ...

Staff Underwriter

West Bend, WI ยท On-site

$68K - $86K/yr

Attend underwriting territory and team meetings to identify important updates, trends and to ... Mentor interns and associates in training by conducting trainee file audits of new business quotes ...

Staff Underwriter

West Bend, WI ยท On-site

$68K - $86K/yr

Attend underwriting territory and team meetings to identify important updates, trends and to ... Mentor interns and associates in training by conducting trainee file audits of new business quotes ...

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Underwriting Trainee Program information

What is the difference between Underwriting Trainee Program vs Underwriter?

AspectUnderwriting Trainee ProgramUnderwriter
CredentialsTypically requires a bachelor's degree, often in finance, economics, or related fieldsRequires relevant experience, certifications (e.g., CPCU), and industry knowledge
Work EnvironmentTraining-focused, entry-level, often in an office settingDecision-making role, responsible for evaluating risks and approving policies
Industry UsageCommonly used for onboarding new talent in insurance companiesEstablished professional role within insurance and reinsurance firms

The Underwriting Trainee Program is designed to train newcomers with foundational knowledge and skills, preparing them for a full underwriting role. In contrast, an Underwriter is an experienced professional responsible for assessing risks and making underwriting decisions. The program serves as a stepping stone toward becoming an underwriter, who typically has more industry experience and certifications.

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

To thrive in an Underwriting Trainee Program, you generally need a bachelor's degree (often in finance, business, or a related field), strong analytical abilities, and numerical proficiency. Familiarity with underwriting software, Microsoft Excel, and sometimes progress toward industry certifications like CPCU is beneficial. Attention to detail, effective communication, and eagerness to learn are standout soft skills for this entry-level role. These skills enable trainees to accurately assess risk, collaborate with teams, and develop into successful underwriters.

What is an Underwriting Trainee Program?

An Underwriting Trainee Program is a structured entry-level development program designed to train individuals in the fundamentals of insurance underwriting. Trainees learn how to assess risks, price insurance policies, and make decisions about coverage under the guidance of experienced underwriters. These programs typically combine classroom instruction, on-the-job training, and mentorship. Upon successful completion, trainees may transition into full-time underwriting positions with increased responsibilities.

What types of projects and responsibilities can I expect to handle during an Underwriting Trainee Program?

As an Underwriting Trainee, you will typically rotate through different lines of business and assist experienced underwriters in evaluating insurance applications, assessing risk, and determining policy terms. You'll be involved in reviewing financial documents, communicating with brokers and clients, and learning about regulatory compliance. The program often includes both classroom training and on-the-job experience, providing a well-rounded introduction to the underwriting process. This hands-on exposure helps you build foundational knowledge and prepares you for more independent underwriting responsibilities after completing the program.
What are popular job titles related to Underwriting Trainee Program jobs in Wisconsin? For Underwriting Trainee Program jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Underwriting Trainee Program jobs in Wisconsin look for? The top searched job categories for Underwriting Trainee Program jobs in Wisconsin are:
What cities in Wisconsin are hiring for Underwriting Trainee Program jobs? Cities in Wisconsin with the most Underwriting Trainee Program job openings:
Infographic showing various Underwriting Trainee Program job openings in Wisconsin as of May 2026, with employment types broken down into 100% Full Time. Highlights an 75% In-person, and 25% Hybrid job distribution.
Underwriting Trainee: Environmental

Underwriting Trainee: Environmental

CapSpecialty

Middleton, WI โ€ข Hybrid

$61K - $87K/yr

Full-time

Life, Retirement, PTO

Posted 5 days ago


Job description

This is a hybrid position requiring 3 days in office at our Middleton, WI office location.ย #LI-Hybrid

At CapSpecialty, we are a specialty underwriting company being driven by well-informed, entrepreneurial and proactive employees. Come join our exciting company where you can really make an impact, and each individual's unique skills and talents are recognized and valued. You will find an accessible leadership team that welcomes opinions and ideas. We owe much of our success to our collaborative environment and set of three guiding principles rooted in customer-centricity, employee excellence and corporate culture.

We offer competitive compensation and benefits packages โ€“ including an innovative open vacation plan, generous paid sick and parental leave, fully vested matching 401k, company-paid group term life insurance and short- & long-term disability plans, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance. Please see our full list of Total Rewardsย here.

CapSpecialty is seeking college graduates for a year-long Underwriting Trainee position on our Environmental Underwriting team.ย Candidates who successfully complete the program will become Underwriters. As an Underwriting Trainee, the individual will get hands on training within the Environmental Underwriting Unit, in addition to time spent with various department heads and leaders across the company to learn more about insurance operations, the history of CapSpecialty, how insurance companies generate profits and the role of reinsurance. Trainees will learn the basics of how to underwrite specialty lines insurance, analyze financial statements, interpret a policy form and interact with CapSpecialtyโ€™s wholesale broker partners. Trainees will participate in department meetings, roundtables, monthly business reviews (MBRs), Joint Accountability Groups (JAGs) and large claim meetings as appropriate. Trainees will spend time with Actuarial, Marketing & Engagement, Claims and Portfolio Management, in addition to accompanying members of the underwriting team on marketing visits. Formal performance evaluations will occur at three, six, nine and 12 months. The Underwriting Training program is designed to provide candidates with the knowledge and skills required to begin a successful underwriting career.ย ย 

Duties/Responsibilities:

  • Candidates will become immersed in the insurance principles they learn so that they have a basic understanding of how to evaluate a risk and can move into a production role upon completion of the Underwriting Training program.
  • Candidates will apply underwriting analysis on actual accounts to support production underwriters.
  • Candidates will begin to develop relationships with their assigned brokers.
  • Candidates will perform other duties as needed.

Supervisory Responsibilities:

None.

Core Competencies:

  • Superior oral and written communication skills coupled with sales skills and an ability to develop relationships with brokers.
  • Skilled in the use of personal computers, the internet and multiple software applications and programs.
  • Ability to work independently, problem solve and meet deadlines while also working on a team as a team player.
  • Strong organizational skills with an attention to detail.

Education and Experience:

  • Bachelorโ€™s degree from an accredited college.
  • Previous office experience helpful.

Physical Demands:

  • Prolonged periods of sitting at a desk and working on a computer.
  • May be required to lift up to 10 lbs. at times.
  • May require business travel up to 15%.

CapSpecialty is a leading provider of specialty insurance and bonds for small- to mid-sized businesses in the U.S., offering casualty, professional liability, surety and fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty's creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty is an operating subsidiary of Berkshire Hathaway, and its carriers have an A+ย ("Superior")ย rating from A.M. Best, writing both admitted and non-admitted policies. For more information, please visitย CapSpecialty.com.

Apply today!

Equal Employment Opportunity Employer