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Remote Sales Associate Jobs in Wisconsin (NOW HIRING)

Retail Territory Sales Associate

Milwaukee, WI · On-site +1

$14.75 - $17/hr

Remote ½ day Fridays * Onsite Health & Wellness Center * Employer 401K contribution in the top 1% ... Supports Associate Manager Sales Planning & Execution in engaging key customer stakeholders to ...

Retail Sales Associate - Part Time

Milwaukee, WI · On-site +1

$14.75 - $17/hr

Join our team as a Retail Sales Associate, where you'll play a key role in delivering WOW! Customer Service by exceeding expectations and making a real difference for our customers. Whether you're ...

$16 - $21.50/hr

A. remote. Role Summary The Associate Service Sales Representative is an entrylevel sales role that supports the U.S. Service Sales organization by generating qualified contract leads and enabling ...

$14.50 - $19.50/hr

A. remote. Role Summary The Associate Service Sales Representative is an entrylevel sales role that supports the U.S. Service Sales organization by generating qualified contract leads and enabling ...

$15 - $20/hr

A. remote. Role Summary The Associate Service Sales Representative is an entrylevel sales role that supports the U.S. Service Sales organization by generating qualified contract leads and enabling ...

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Showing results 1-20

Remote Sales Associate information

See Wisconsin salary details

$8

$19

$41

How much do remote sales associate jobs pay per hour?

As of Aug 15, 2026, the average hourly pay for remote sales associate in Wisconsin is $19.04, according to ZipRecruiter salary data. Most workers in this role earn between $13.61 and $19.81 per hour, depending on experience, location, and employer.

What is a remote sales associate?

A Remote Sales Associate is a professional who sells products or services to customers while working outside of a traditional office setting, often from home or another remote location. Their responsibilities typically include reaching out to potential clients, answering inquiries, presenting product information, and closing sales using phone, email, or online platforms. This role requires strong communication skills, self-motivation, and the ability to work independently. Remote Sales Associates often use digital tools to manage leads, track sales, and collaborate with their team virtually.

What is the difference between Remote Sales Associate vs Remote Customer Service Representative?

AspectRemote Sales AssociateRemote Customer Service Representative
Required CredentialsSales experience, communication skills, sometimes sales certificationsCustomer service skills, communication, problem-solving
Work EnvironmentRemote, often sales-focused, target-drivenRemote, customer support-focused, service-oriented
Employer & Industry UsageSales departments across retail, tech, telecommunicationCustomer support across various industries like retail, tech, healthcare
Search & Comparison IntentLooking for sales roles, commission-based jobsSeeking customer support roles, service jobs

While both roles are remote and require strong communication skills, a Remote Sales Associate focuses on selling products or services and meeting sales targets, often with commission incentives. In contrast, a Remote Customer Service Representative handles customer inquiries, resolves issues, and provides support without a primary focus on sales. Understanding these differences helps job seekers find roles aligned with their skills and career goals.

What are the key skills and qualifications needed to thrive as a remote sales associate?

To thrive as a Remote Sales Associate, you need strong communication, persuasive selling abilities, and a solid understanding of sales strategies, typically supported by experience or a relevant degree. Familiarity with Customer Relationship Management (CRM) tools like Salesforce, virtual meeting platforms, and sales tracking software is essential. Self-motivation, resilience, and time management are crucial soft skills for excelling in a remote environment. These skills and qualities enable effective customer engagement, efficient remote work, and consistent achievement of sales targets.

How do remote sales associates typically stay connected with their team and clients while working from home?

Remote Sales Associates rely heavily on digital communication tools such as video conferencing, instant messaging, and CRM platforms to collaborate with team members and maintain client relationships. Regular virtual meetings and daily check-ins are common practices to ensure alignment on goals and strategies. Staying organized and proactive with follow-ups is crucial, as remote work requires a higher level of self-motivation and clear communication to overcome the lack of in-person interaction.

Can you get into a remote sales associate with no experience?

Remote sales associate positions often do not require prior experience, as many companies provide training on sales techniques and tools like CRM software. Strong communication skills, a proactive attitude, and the ability to learn quickly can help candidates qualify for entry-level roles without previous sales experience.

What are the most commonly searched types of Remote Sales jobs in Wisconsin?

The most popular types of Remote Sales jobs in Wisconsin are:

What cities in Wisconsin are hiring for Remote Sales Associate jobs?

Cities in Wisconsin with the most Remote Sales Associate job openings:

Infographic showing various Remote Sales Associate job openings in Wisconsin as of August 2026, with employment types broken down into 77% Full Time, 22% Part Time, and 1% Contract. Highlights an 92% Physical, 1% Hybrid, and 7% Remote job distribution, with an average salary of $39,606 per year, or $19 per hour.

Medicare Sales Associate (seasonal-temporary)

WPS Health Solutions

Madison, WI • On-site, Remote

$14 - $19.25/hr

Full-time

Medical, Dental, Retirement, 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

128th of 308 rated insurance


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.


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