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Remote Mailing Jobs in Wisconsin (NOW HIRING)

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Remote Mailing information

What are some common challenges faced in a Remote Mailing position and how can they be managed?

In a Remote Mailing role, one common challenge is ensuring timely and accurate handling of physical mail while working away from a centralized office. This often requires strict organization, reliable access to mailing supplies, and effective communication with supervisors and team members to coordinate pick-ups, drop-offs, or digital tracking. To manage these challenges, remote mail clerks typically establish clear routines, utilize digital tools for tracking correspondence, and maintain organized records to avoid errors or delays. Staying proactive in communication with both internal teams and external mailing services is key to ensuring smooth workflow.

What are the key skills and qualifications needed to thrive in a Remote Mailing position, and why are they important?

To thrive in a Remote Mailing position, you need strong organizational skills, attention to detail, and a high school diploma or equivalent. Familiarity with mailing software, database management systems, and basic office equipment is often required. Reliability, time management, and clear communication are important soft skills for managing tasks independently and ensuring accuracy. These skills are crucial for maintaining efficient operations and timely delivery in a remote work environment.

What is remote mailing?

Remote mailing refers to the process of managing and sending mail—such as letters, packages, or documents—without being physically present at a mailing facility or office. Individuals or companies use digital tools and online services to upload documents, which are then printed, packaged, and mailed by third-party providers. This job can involve tasks like preparing digital files, managing addresses, and tracking deliveries, all from a remote location. Remote mailing is popular for businesses seeking efficient, contactless, or geographically flexible mailing solutions.

What is the difference between Remote Mailing vs Remote Data Entry?

AspectRemote MailingRemote Data Entry
Required SkillsMail handling, organization, basic computer skillsData input, accuracy, typing speed
Work EnvironmentHome office, mailroom, or administrative settingHome office, administrative or data management setting
CertificationsNone typically required, basic computer literacyNone typically required, but fast typing and accuracy are preferred
Industry UsageLogistics, administrative support, mailing servicesBusiness, healthcare, finance, administrative support

Remote Mailing and Remote Data Entry share similarities in working remotely and requiring basic computer skills. However, Remote Mailing focuses on handling physical mail and organizational tasks, while Remote Data Entry emphasizes inputting digital data accurately. Both roles are common in administrative and support industries, but they serve different operational needs.

What are the most commonly searched types of Mailing jobs in Wisconsin? The most popular types of Mailing jobs in Wisconsin are:
What are popular job titles related to Remote Mailing jobs in Wisconsin? For Remote Mailing jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Remote Mailing jobs in Wisconsin look for? The top searched job categories for Remote Mailing jobs in Wisconsin are:
Remote Mailing jobs near you
Infographic showing various Remote Mailing job openings in Wisconsin as of July 2026, with employment types broken down into 100% Full Time. Highlights an 100% Remote job distribution.
Part Time Underwriter Assistant (Seasonal)

Part Time Underwriter Assistant (Seasonal)

WPS Health Solutions

Madison, WI • On-site, Remote

$19.75 - $27/hr

Part-time

Medical, PTO

This job post has expired today. Applications are no longer accepted.

WPS Health Solutions rating

8.3

Company rating: 8.3 out of 10

Based on 5 frontline employees who took The Breakroom Quiz

108th of 281 rated insurance

Job description

The Underwriting Assistant is responsible for supporting the underwriter with quotes, new business and existing business. This role is responsible for data collection, quote preparation, documentation management, and ensuring compliance with internal guidelines and regulatory requirements. The Underwriter Assistant will review and request missing paperwork needed for new business, renewals and changes. This position will provide clear communication with our internal teams regarding what is needed or what is changing for groups. The assistant plays a critical support role in helping underwriters make timely, accurate risk decisions and maintain a smooth workflow. 

Additional information

  • ~$20/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:

  • Enoy reviewing quoting data for completeness and request additional information, if necessary, prepare and index all documents into the underwriting system. Upload data to the web tool to aid in underwriting.
  • Have prepared renewal packets including the correct addendums and SBCs for mailing.
  • Can complete group set-up and configuration sheets for new groups, renewal groups, and changes utilizing appropriate underwriting guidelines. Ensure information is entered accurately into the underwriting system for routing to other departments.
  • Like to create rate calculators for renewal and quotes.
  • Can maintain tracking systems for groups requesting quotes and renewal groups.
  • Have researched information on a group or individuals within a group to aid in the underwriting process.
  • Enjoy interfacing with sales staff and other departments to resolve rate and benefit issues.
  • Can review all new groups to make sure they are not on Specially Designated Nationals List (SDN). [Watch Dog] and Assign group numbers.
  • Likes to provide renewal reports to the assigned underwriter to support renewal rate decisions.
  • Have ensured compliance with internal guidelines and applicable regulations (i.e., ACA, HIPPA).

Minimum Qualifications

  • High School Diploma or GED or equivalent experience
  • 1 or more years of experience in health insurance, underwriting, or related administrative support role.
  • Proficiency with Microsoft Excel, Word, and Outlook.
  • Detail-oriented with a commitment to data accuracy.
  • Strong organizational and time management skills.
  • Strong written and verbal communication skills.
  • Ability to handle confidential information appropriately.
  • Familiarity with group health plans, medical underwriting practices, and industry terminology preferred.
  • Experience with health plan quoting tools or underwriting systems is preferred.

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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