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Remote Insurance Underwriter Trainee Jobs in Wisconsin

WPS

Part Time Senior Underwriter (Seasonal)

Madison, WI · On-site +1

$40/hr

Enjoy negotiating group health insurance rates and benefits with sales and external brokers. * Can ... Remote Work Requirements * High speed cable or fiber * Minimum of 10 Mbps downstream and at least 1 ...

Understory

Underwriter

Madison, WI · On-site +1

Guiding the review of insurance applications to gauge the degree of risk involved accurately ... Exceptional remote candidates may be considered. Compensation includes: * Competitive base salary ...

WPS

Part Time Underwriter Assistant (Seasonal)

Madison, WI · On-site +1

$19.75 - $27/hr

Schedule - Part Time Shift between: (8:00 AM CT - 5:00 PM CT) Work Location We are open to remote ... WPS offers health insurance plans for individuals, families, seniors and group health plans for ...

CSAA

Job Title Commercial Insurance Consultant, Claims Insights- Remote Requisition Number R7770 ... Collaborate with partners across Claims, Product, Underwriting, Actuarial, Finance, and Technology ...

CSAA

Job Title Commercial Insurance Consultant, Claims Insights- Remote Requisition Number R7770 ... Collaborate with partners across Claims, Product, Underwriting, Actuarial, Finance, and Technology ...

CSAA

Job Title Commercial Insurance Consultant, Claims Insights- Remote Requisition Number R7770 ... Collaborate with partners across Claims, Product, Underwriting, Actuarial, Finance, and Technology ...

CSAA

Job Title Commercial Insurance Consultant, Claims Insights- Remote Requisition Number R7770 ... Collaborate with partners across Claims, Product, Underwriting, Actuarial, Finance, and Technology ...

InsuraTec

Sales Representative (Remote)

Wausau, WI · Remote

... insurance license and sharpen sales skills. * Underwriting Collaboration : Work closely with ... Remote Flexibility : Enjoy the freedom to work from home on your schedule. * Work-Life Balance

InsuraTec

Sales Representative (Remote)

Verona, WI · Remote

... insurance license and sharpen sales skills. * Underwriting Collaboration : Work closely with ... Remote Flexibility : Enjoy the freedom to work from home on your schedule. * Work-Life Balance

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Remote Insurance Underwriter Trainee information

What is the difference between Remote Insurance Underwriter Trainee vs Remote Insurance Underwriter?

AspectRemote Insurance Underwriter TraineeRemote Insurance Underwriter
Required CredentialsTypically a bachelor's degree; some certifications beneficialRelevant certifications (e.g., CPCU, AIC) often required or preferred
Work EnvironmentTraining phase, supervised, entry-levelFull responsibilities, independent decision-making
Job ResponsibilitiesLearning underwriting processes, assisting with risk assessmentAssessing risks, approving policies, managing complex cases

The Remote Insurance Underwriter Trainee is an entry-level role focused on learning and supporting underwriting tasks, often requiring minimal experience. In contrast, the Remote Insurance Underwriter handles full underwriting responsibilities, making independent decisions. The trainee position is ideal for those starting their career, while the underwriter role is suited for experienced professionals with relevant certifications.

What are popular job titles related to Remote Insurance Underwriter Trainee jobs in Wisconsin? For Remote Insurance Underwriter Trainee jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Remote Insurance Underwriter Trainee jobs in Wisconsin look for? The top searched job categories for Remote Insurance Underwriter Trainee jobs in Wisconsin are:
What cities in Wisconsin are hiring for Remote Insurance Underwriter Trainee jobs? Cities in Wisconsin with the most Remote Insurance Underwriter Trainee job openings:
Remote Insurance Underwriter Trainee jobs near you
Infographic showing various Remote Insurance Underwriter Trainee job openings in Wisconsin as of July 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, 1% Temporary, and 4% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution.
Part Time Senior Underwriter (Seasonal)

Part Time Senior Underwriter (Seasonal)

WPS

Madison, WI • On-site, Remote

$40/hr

Part-time

Medical, PTO

This job post has expired 1 day ago. Applications are no longer accepted.

Job description

The Senior Underwriter is responsible for analyzing and assessing the risk of new business quotes and existing business renewals for fully insured and Administrative Service Only groups. Responsible for ensuring profitability, customer satisfaction, and corporate goals/objectives for each assigned account. The Senior Underwriter provides technical advice/ support to less experienced underwriters within all aspects of the underwriting process. The role provides support to assist in new group sales and retention of commercial business. The Senior Underwriter is responsible for the premium development of future risk which in turn has a direct impact on a group's loss ratio and financial position of the health insurance division.
Additional information
  • ~$40/hour (pay is based on individual experience)
  • Seasonal Timeline: August 2026 - January 2027
  • Schedule - Part Time Shift between: (8:00 AM CT - 5:00 PM CT)

Work LocationWe are open to remote work in the following approved states:
Colorado, Florida, Georgia, Illinois, Indiana, Iowa, Michigan, Minnesota, Missouri, Nebraska, New Jersey, North Carolina, Ohio, South Carolina, Texas, Virginia, Wisconsin
How do I know this opportunity is right for me? If you:
  • Have prepared and produced New Business Proposals that meet corporate turnaround times, RFP timelines, profitability, quality and customer satisfaction.
  • Can produce existing group renewals, alternative benefit designs, benefit changes, and high-cost claimant projections for fully insured and self-funded groups that meet corporate turnaround times, profitability, quality, and customer satisfaction.
  • Like to collaborate with management and advise on the appropriate renewal pricing for all existing non-ACA Association blocks of business.
  • Enjoy negotiating group health insurance rates and benefits with sales and external brokers.
  • Can attend New Business & Change Group Intake meetings internally and externally with the clients to ensure accurate benefit and claim payment setup.
  • Like to assist Sales Managers & Account Representatives with questions, concerns, and details in regard to new/existing accounts.
  • Enjoy developing and maintaining strong relationships with brokers, consultants, and internal stakeholders to support account retention and acquisition.
  • Have maintained existing databases, spreadsheets, underwriting guidelines and manuals with vital underwriting information for internal and external use.
  • Can identify deficiencies and possible enhancements in department administrative policies and procedures that affect customer satisfaction and corporate profitability.
  • Like to stay current on industry trends, regulatory changes (ACA, ERISA, HIPAA), and competitor activity that impact underwriting practices. Ensure compliance with internal controls and external regulatory standards.

Minimum Qualifications
  • Bachelor's Degree in Business, Actuarial Science, Finance, Mathematics, Healthcare Administration or related field or equivalent combination of education and experience.
  • 5 or more years of experience in health insurance underwriting.
  • Strong knowledge and understanding of group rating methodologies, funding arrangements (fully insured, level-funded, self-funded), and risk adjustment.
  • Proficiency in Microsoft Office Suite and underwriting/pricing tools.
  • Experience with health plan systems and CRM platforms.
  • Exceptional analytical and decision-making skills.
  • Strong communication and presentation abilities.
  • Strong knowledge of current Federal and State health insurance regulations.
  • Ability to manage multiple priorities and meet deadlines in a fast-paced environment.

Preferred Qualifications
  • Experience with WPS systems and processes, including: OnBase, Facets, WebMUGs.

Remote Work Requirements
  • High speed cable or fiber
  • Minimum of 10 Mbps downstream and at least 1 Mbps upstream internet connection (can be checked at https://speedtest.net).
  • Please review Remote Worker FAQs for additional information.

Benefits
  • Remote and hybrid work options available
  • Prorated Holiday Pay and On-Demand PTO

Who We Are
WPS, a health solutions company, is a leading not-for-profit health insurer and federal government contractor headquartered in Madison, Wisconsin. WPS offers health insurance plans for individuals, families, seniors and group health plans for small to large businesses. We process claims and provide customer support for beneficiaries of the Medicare program and manage benefits for millions of active-duty and retired military personnel across the U.S. and abroad. WPS has been making healthcare easier for the people we serve for nearly 80 years. Proud to be military and veteran ready.
Culture Drives Our Success
WPS' culture is where the great work and innovations of our people are seen, fueled and rewarded. We accomplish this by creating an open and empowering employee experience. We recognize the benefits of employee engagement as an investment in our workforce-both current and future-to effectively seek, leverage, and include differing and unique perspectives that fuel agility and innovation on high-performing teams. This results in people bringing their authentic selves to work every day in an organization that successfully adapts to business changes and new opportunities.
We are proud of the recognition we have received from local and national organization regarding our culture and workplace: WPS Newsroom - Awards and Recognition.
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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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