Remote Independent Contractor Jobs in Madison, WI

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.