2

Remote Insurance Underwriter Jobs in Wisconsin (NOW HIRING)

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Insurance Agent

Madison, WI · Remote

$69K - $150K/yr

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

Remote Insurance Agent

Milwaukee, WI · Remote

$69K - $150K/yr

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

Remote Insurance Agent

Green Bay, WI · Remote

$69K - $150K/yr

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

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 ...

$105K - $124K/yr

This is a remote role open to any location in continental US Manulife is a leading international ... In addition to those performed by Underwriter Consultants - identify and provide solutions to work ...

$105K - $124K/yr

This is a remote role open to any location in continental US Manulife is a leading international ... In addition to those performed by Underwriter Consultants - identify and provide solutions to work ...

$98K - $115K/yr

This is a remote role open to any location in continental US Manulife is a leading international ... In addition to those performed by Underwriter Consultants - identify and provide solutions to work ...

$98K - $115K/yr

This is a remote role open to any location in continental US Manulife is a leading international ... In addition to those performed by Underwriter Consultants - identify and provide solutions to work ...

$95K - $113K/yr

This is a remote role open to any location in continental US Manulife is a leading international ... In addition to those performed by Underwriter Consultants - identify and provide solutions to work ...

$95K - $113K/yr

This is a remote role open to any location in continental US Manulife is a leading international ... In addition to those performed by Underwriter Consultants - identify and provide solutions to work ...

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Insurance Representative | Flexible Schedule | Commission-Based This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

Remote Sales Agent

Madison, WI · Remote

$69K - $150K/yr

Remote Insurance Representative | Flexible Schedule | Commission Only This position offers flexible work hours and clear paths for advancement into leadership and management. You will work remotely ...

New

next page

Showing results 1-20

Remote Insurance Underwriter information

See Wisconsin salary details

$32.8K

$79.6K

$140.8K

How much do remote insurance underwriter jobs pay per year?

As of Jul 19, 2026, the average yearly pay for remote insurance underwriter 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 are some common challenges faced by remote insurance underwriters and how can they be managed?

Remote insurance underwriters often face challenges such as maintaining effective communication with team members and staying updated on changing underwriting guidelines. Working remotely requires strong self-discipline to manage workloads across multiple cases and deadlines without direct in-person supervision. Utilizing collaboration tools, setting regular check-ins with colleagues, and staying proactive in seeking clarification on complex cases can help overcome these challenges. Additionally, remote underwriters should take advantage of ongoing training resources to keep their skills and industry knowledge current.

What Does a Remote Insurance Underwriter Do?

The job duties of a remote insurance underwriter focus on assessing the risk in insurance policies. In this virtual position, you work from home or from a remote office to evaluate the risk of each client who has applied. You may also review insurance coverage for excessive risk. After reviewing financial documents, risk assessments, and insurance needs, your responsibilities include deciding whether to approve or deny an insurance application. Underwriting may require you to deny coverage for clients that you deem high risk.

What are the key skills and qualifications needed to thrive as a Remote Insurance Underwriter, and why are they important?

To thrive as a Remote Insurance Underwriter, you need strong analytical abilities, attention to detail, and a solid understanding of risk assessment and insurance principles, typically backed by a bachelor’s degree in finance, business, or a related field. Proficiency with underwriting software, risk management systems, and familiarity with industry certifications like CPCU or AU is highly valued. Excellent written communication, time management, and decision-making skills help remote underwriters collaborate effectively and manage workloads independently. These skills ensure accurate risk evaluations, compliance with regulations, and efficient remote operations within the insurance sector.

What is a remote insurance underwriter?

A remote insurance underwriter is a professional who evaluates insurance applications, assesses risk, and determines policy terms and premiums, all while working from a location outside of a traditional office, such as from home. They review documentation, analyze data, and make recommendations using digital tools and communication platforms. This role requires strong analytical skills, attention to detail, and knowledge of insurance regulations and guidelines. Remote underwriters often collaborate with agents, brokers, and clients electronically to ensure accurate policy issuance and risk management.

Can you work remotely as an insurance underwriter?

Yes, many insurance underwriters work remotely, especially with advances in digital communication and underwriting software. Remote positions often require strong analytical skills, industry certifications, and familiarity with underwriting tools, and they may involve regular virtual meetings and collaboration.

What is the difference between Remote Insurance Underwriter vs Remote Insurance Claims Adjuster?

AspectRemote Insurance UnderwriterRemote Insurance Claims Adjuster
Required CredentialsInsurance licenses, underwriting certificationsClaims adjusting licenses, insurance certifications
Work EnvironmentOffice or remote, analyzing risk dataRemote, investigating claims and assessing damages
Employer & Industry UsageInsurance companies, brokers, underwritersInsurance companies, third-party claims firms

Remote Insurance Underwriters and Claims Adjusters both work in the insurance industry, often remotely, but focus on different aspects. Underwriters evaluate risk to determine policy terms, while Claims Adjusters investigate and settle claims. Both roles require specific licenses and certifications, and are essential in the insurance process, but they serve distinct functions within the industry.

How can I make $2000 a week working from home?

A remote insurance underwriter can potentially earn $2000 or more per week by working full-time, gaining specialized knowledge, and obtaining relevant certifications. Increasing experience, working for high-paying companies, and handling a higher volume of policies can also boost income. Building strong analytical skills and proficiency with underwriting software are essential for maximizing earning potential.

Will underwriters be replaced by AI?

Remote insurance underwriters analyze risk data and determine policy terms, and AI tools are increasingly used to assist with data analysis and automation. While AI can handle routine tasks, underwriters' expertise in judgment, complex decision-making, and customer interaction remains essential, making full replacement unlikely in the near term.

Can underwriting be done remotely?

Remote insurance underwriters can perform their duties from outside traditional office settings, utilizing digital tools and underwriting software. Many companies now offer remote positions, especially for experienced underwriters with strong analytical skills and industry certifications. However, some roles may require occasional in-office meetings or collaboration with teams.
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 cities in Wisconsin are hiring for Remote Insurance Underwriter jobs? Cities in Wisconsin with the most Remote Insurance Underwriter job openings:
Infographic showing various Remote Insurance Underwriter job openings in Wisconsin as of July 2026, with employment types broken down into 92% Full Time, and 8% Part Time. Highlights an 8% In-person, and 92% Remote job distribution, with an average salary of $79,616 per year, or $38.3 per hour.
Part Time Senior Underwriter (Seasonal)

Part Time Senior Underwriter (Seasonal)

WPS Health Solutions

Madison, WI • On-site, Remote

$40/hr

Part-time

Medical, PTO

Posted 8 days ago


WPS Health Solutions rating

8.3

Company rating: 8.3 out of 10

Based on 5 frontline employees who took The Breakroom Quiz

110th of 281 rated insurance


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 Location
We 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.

Sign up for Job Alerts

FOLLOW US!

Instagram

LinkedIn

Facebook

WPS Health Blog  


What WPS Health Solutions employees say

Pay

Hours and flexibility

Workplace

Get the full story on Breakroom