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Remote Military Jobs in Wisconsin (NOW HIRING)

WPS

Medicare Sales Associate (seasonal-temporary)

Madison, WI · On-site +1

$14 - $19.25/hr

Remote Training, Mon-Fri 8am-4:30pm Central Time * Scheduled Shift: 8am-4:30pm CT or 8:30am-5pm CT ... Proud to be military and veteran ready. Culture Drives Our Success WPS' culture is where the great ...

WPS

Senior Account Manager - Health Insurance

Madison, WI · On-site +1

$85K - $105K/yr

Remote work Wisconsin - this position will have travel in the State of Wisconsin. *As a secondary ... Proud to be military and veteran ready. Culture Drives Our Success WPS' culture is where the great ...

Ascension

Medical Coder

Milwaukee, WI · Remote

$23.03 - $31.16/hr

Remote Department: Revenue Cycle Management Schedule: Full-time | Day Shift Salary Range: $23.03 ... Recognized as one of the Best 150+ Places to Work in Healthcare and a Military-Friendly Gold ...

Ascension

Talent Acquisition Director

Milwaukee, WI · Remote

$102K - $140K/yr

Remote with up to 15% travel Department: Talent Acquisition Schedule: Day shift | Full-time Salary ... Recognized as one of the Best 150+ Places to Work in Healthcare and a Military-Friendly Gold ...

Ascension

Medical Coder

Milwaukee, WI · Remote

$23.03/hr

Remote Department: Revenue Cycle Management Schedule: Full-time | Day Shift Salary Range: $23.03 ... Recognized as one of the Best 150+ Places to Work in Healthcare and a Military-Friendly Gold ...

Ascension

Talent Acquisition Director

Milwaukee, WI · Remote

$152K/yr

Remote with up to 15% travel Department: Talent Acquisition Schedule: Day shift | Full-time Salary ... Recognized as one of the Best 150+ Places to Work in Healthcare and a Military-Friendly Gold ...

Katch

Recovery Specialist

Green Bay, WI · On-site +1

This remote position requires that candidates reside in the following eligible states: Georgia ... status, citizenship, military or veteran status, or any other characteristic protected by ...

New

Ascension

Medical Staff Services Manager

Glendale, WI · Remote

Remote (candidate must be located in Wisconsin) Facility: Remote Department: Medical Affairs Admin ... Recognized as one of the Best 150+ Places to Work in Healthcare and a Military-Friendly Gold ...

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All JobsMilitary JobsRemote Military JobsRemote Military Jobs in Wisconsin

Remote Military information

What are some common challenges faced when working as a remote military team member, and how can they be addressed?

Remote military roles often involve unique challenges such as maintaining clear communication across time zones, ensuring data security, and staying connected with the unit’s mission. Team members may experience a sense of isolation or difficulty accessing resources typically available on base. To address these challenges, it’s important to establish regular communication routines, utilize secure collaboration platforms, and actively seek support from supervisors and peers to stay engaged and informed.

What are the key skills and qualifications needed to thrive as a remote military operations specialist, and why are they important?

To thrive as a Remote Military Operations Specialist, you need a solid background in military strategy, situational awareness, and often a relevant degree or military training. Proficiency with secure communication systems, geospatial intelligence software, and unmanned systems platforms is typically required. Attention to detail, critical thinking, and the ability to remain calm under pressure are essential soft skills for success. These competencies are crucial for ensuring mission effectiveness, operational security, and rapid decision-making in high-stakes environments.

What are remote military jobs?

Remote military jobs are positions within the military or defense sector that can be performed from a location outside of a traditional military base or office, often leveraging technology for communication and operations. These roles might include intelligence analysis, cybersecurity, administrative support, logistics coordination, and IT support. They enable military personnel, veterans, or civilians to contribute to national defense missions while working from home or other remote locations. The availability of remote military jobs has expanded with advancements in secure communication and data handling technologies.

What is the difference between Remote Military vs Remote Security Guard?

AspectRemote MilitaryRemote Security Guard
Required CredentialsMilitary experience, security clearances, specialized trainingSecurity certifications, background checks, basic training
Work EnvironmentMilitary operations, secure facilities, remote communicationClient sites, remote monitoring, surveillance systems
Employer & Industry UsageMilitary agencies, defense contractors, governmentPrivate security firms, corporate clients, retail

Remote Military roles typically require military experience and security clearances, focusing on defense and security operations. Remote Security Guard positions often need security certifications and involve monitoring and protecting property remotely. While both roles involve security, Remote Military positions are more specialized and often linked to government agencies, whereas Remote Security Guards work mainly for private firms and clients.

What are the most commonly searched types of Military jobs in Wisconsin? The most popular types of Military jobs in Wisconsin are:
What are popular job titles related to Remote Military jobs in Wisconsin? For Remote Military jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Remote Military jobs in Wisconsin look for? The top searched job categories for Remote Military jobs in Wisconsin are:
What cities in Wisconsin are hiring for Remote Military jobs? Cities in Wisconsin with the most Remote Military job openings:
Remote Military jobs near you
Infographic showing various Remote Military job openings in Wisconsin as of July 2026, with employment types broken down into 1% As Needed, 80% Full Time, 18% Part Time, and 1% Contract. Highlights an 98% Physical, 1% Hybrid, and 1% Remote job distribution.

Medicare Sales Associate (seasonal-temporary)

WPS

Madison, WI • On-site, Remote

$14 - $19.25/hr

Full-time

Medical, Dental, Retirement, PTO

Re-posted 6 days ago

Job description

Role Snapshot
The Medicare Sales Associate supports the direct sales team through inbound and outbound call management. The role is accountable to solicit new business, set appointments for sales presentations, collect and document information in the CRM, enroll new customers, and support retention efforts.
Additional Information
  • Start Date: August 25, 2026
  • Starting Base Salary: 21.00/hr. (may fluctuate based on experience)
  • Training Location/Schedule: Remote Training, Mon-Fri 8am-4:30pm Central Time
  • Scheduled Shift: 8am-4:30pm CT or 8:30am-5pm CT. Mon-Fri.
  • Position is a seasonal role, slated to go from August to December, 2026.

Work Location
We are open to remote work (from home) 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 enjoy the following activities:
  • Support new business sales initiatives and provide backup support for the agency sales team.
  • Provide information to prospective members on Medicare and plan options to drive growth and achieve sales goals.
  • Assist with prospect follow-ups, scheduling, and documentation in the CRM.
  • Provide support for webinars including pre-webinar reminders and chat support.
  • Identify prospective member needs and assist in enrollment or re-enrollment to Medicare Supplement plans.
  • Other job-related responsibilities may be assigned as required.

Minimum Qualifications
  • U.S. citizenship is required for this position due to Department of Defense restrictions.
  • High school diploma or equivalent.
  • Valid Wisconsin Life & Health Insurance Intermediary License or obtained within 60 days of hire.
  • One (1) or more years of health insurance, customer service or sales experience.
  • Basic knowledge and understanding of Medicare and Medicare Supplement plans.
  • Ability to work both independently and part of a team.
  • Ability to adapt and thrive in a fast-paced environment.
  • Proficiency in Microsoft Office Suite.

Preferred Qualifications
  • Bachelor's degree in Business, Marketing, Healthcare Administration or related field preferred.
  • Proficiency in CRM software preferred.
  • Experience with phone sales.

Remote Work Requirements
  • Wired (ethernet cable) internet connection from your router to your computer.
  • 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
  • Performance bonus and/or merit increase opportunities
  • 401(k) with a 100% match for the first 3% of your salary and a 50% match for the next 2% of your salary (100% vested immediately)
  • Competitive paid time off
  • Health insurance, dental insurance, and telehealth services start DAY 1
  • Professional and Leadership Development Programs
  • Review additional benefits: (https://www.wpshealthsolutions.com/careers/)

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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TRICARE (MVH)
This position supports services under U.S. Department of Defense (DoD) Defense Health Agency (DHA) contract(s). As such, the role is subject to all applicable federal regulations, DoD contract requirements, and WPS internal policies, including but not limited to standards for data security, privacy, confidentiality, and program integrity. DoD contractors and their personnel are subject to screening and background investigation prior to being granted access to information systems and/or sensitive data to safeguard government resources that provide critical services.
Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities
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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