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Second Chance Remote Jobs in Sun Prairie, WI (NOW HIRING)

Remote Customer Service Representative

Madison, WI · On-site +1

$16.25 - $22/hr

What You Need to Thrive in Our Remote Environment: * Cable or Fiber Internet Service only (no dial-up, DSL, satellite or cellular) * 25Mbps Download/10Mbps Upload * Ping Rate - Less than 100 ms * A ...

Customer Representative

Mcfarland, WI · Remote

$30K - $50K/yr

Perks * 100% remote work with flexible scheduling. * Opportunities for growth within the agency. * Travel perks and exclusive industry discounts. * Supportive team environment with ongoing training.

Second Chance Remote information

What is a second chance remote?

Second Chance Remote jobs are employment opportunities offered by companies that are open to hiring individuals with criminal records or those seeking a fresh start after past mistakes. These jobs are typically remote, meaning you can work from home or anywhere with internet access. Employers offering second chance opportunities believe in giving people the ability to rebuild their lives, often providing support, training, and flexible positions. Such roles can range from customer service and data entry to IT and creative work. Second chance remote jobs help break down the barriers to employment for those with non-traditional backgrounds.

What are the key skills and qualifications needed to thrive in a second chance remote position, and why are they important?

To thrive in a second chance remote position, you generally need a high school diploma or GED, basic computer literacy, and a willingness to learn. Familiarity with remote collaboration tools like Zoom, Microsoft Teams, and cloud-based platforms is often required. Strong communication, self-motivation, and reliability help candidates stand out and build trust with employers. These skills are important because they demonstrate your ability to contribute productively and responsibly in a remote work environment, regardless of your background.

What unique challenges might I encounter when working in a second chance remote role, and how can I overcome them?

Second Chance Remote roles often involve supporting individuals with prior barriers to employment, such as past incarceration or significant career gaps. You may encounter challenges such as building trust with clients, navigating complex personal situations, and balancing empathy with accountability. Overcoming these challenges requires strong communication skills, patience, and a commitment to fostering a supportive, nonjudgmental environment. Collaboration with social services, employers, and team members is essential to provide comprehensive support and help clients succeed in their roles.

What is the difference between Second Chance Remote vs Customer Service Representative?

AspectSecond Chance RemoteCustomer Service Representative
Required CredentialsHigh school diploma or equivalent; background checkHigh school diploma or equivalent; training provided
Work EnvironmentRemote, home-basedRemote or in-office, customer-facing
Industry UsageEmployers seeking second chance employment candidatesCustomer service across various industries
Common Search IntentJobs for individuals with background challengesCustomer support roles

Second Chance Remote and Customer Service Representative roles often require similar credentials and work environments. However, Second Chance Remote specifically targets candidates with past background challenges, offering remote opportunities in customer service. While both roles involve communication skills, Second Chance Remote emphasizes providing employment opportunities for those seeking a second chance, whereas Customer Service Representatives may have broader eligibility criteria.

What are popular job titles related to Second Chance Remote jobs in Sun Prairie, WI?

For Second Chance Remote jobs in Sun Prairie, WI, the most frequently searched job titles are:

What job categories do people searching Second Chance Remote jobs in Sun Prairie, WI look for?

The top searched job categories for Second Chance Remote jobs in Sun Prairie, WI are:

What cities near Sun Prairie, WI are hiring for Second Chance Remote jobs?

Cities near Sun Prairie, WI with the most Second Chance Remote job openings:

Infographic showing various Second Chance Remote job openings in Sun Prairie, WI as of June 2026, with employment types broken down into 69% Full Time, 26% Part Time, and 5% Contract. Highlights an 35% Physical, 3% Hybrid, and 62% Remote job distribution.

Customer Service Rep, Pay is $17.75/hr, 2nd Shift position - 10:25am - 7:00pm CS - (Must live wi...

WPS Health Solutions

Madison, WI • On-site, Remote

$18.50/hr

Full-time

Medical, Dental, Retirement, PTO

Posted 15 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

129th of 311 rated insurance


Job description

U.S. citizenship is required for this position due to Department of Defense restrictions
Bargaining Unit position - Must live within 45 miles of WPS Headquarters (1717 W. Broadway in Madison, WI, 53713)

We are seeking talented Customer Service Reps / Customer Care Specialists to join our team! The successful candidate will play a critical role in providing call center telephone support, as well as responses to written inquiries submitted by, military members, retirees, and dependents eligible for both TRICARE and Medicare benefits. In addition, this role is responsible for assisting with claims and billing inquiries from hospitals and clinics. Inquiries can include questions about claims, benefits, and eligibility. Success is accomplished by navigating multiple systems to research and resolve complex inquiries with a clear, accurate, and easy to understand response. This is a Bargaining Unit / Union position.

Additional Information

  • Start Date: 9/22/26
  • Starting Pay: $17.75/hour plus a 2nd Shift differential after training of $.75/hour.
  • Training Location/Schedule:
    • Training: First 8 weeks from 8:00am-4:35pm CST Monday-Friday
    • Scheduled Shift: Once training is completed, this will be a 2nd Shift role – 10:25am - 7:00pm CST
    • Potential on-site training to be determined.
    • All Onsite training will take place at the WPS Corporate Center Building (1717 W. Broadway) in Madison, WI
  • Work Location: Once training is complete you may have the option to work remote or onsite. Please note that the assigned office for this position is in Madison, WI and remote employees may be required to work at this location at times. 

In this role you will:

  • Receive telephone, written, fax, and e-mail inquiries concerning TRICARE eligibility, benefits determinations, and claims adjudication questions or billing problems.
  • Apply appropriate provisions of TRICARE regulations, interpretations, and procedural directives in making determinations on eligibility and benefits to determine appropriate responses to inquiries.
  • Obtain and analyze claims data to determine specific problem areas including external communication to obtain data.
  • Complete research and provide final resolution to inquiries within contractual requirements.
  • Communicate with inquirers to determine appropriate authorization or referral of services.
  • Submit claims for adjudication, correction, payment, or review as appropriate.
  • Educate providers on billing requirements of TRICARE to reduce claim problems.
  • Deal tactfully with people in a wide variety of situations to convey a favorable corporate image.
  • Respond to inquirers using various forms of communication (written letter, telephone, web, or email) within time frames to exceed contractual standards.
  • Collect and record data for Customer Service records and computer analysis.
  • Inform supervisory staff of system problems when identified, researching problems to provide backup data and examples when needed.

How do I know this opportunity is right for me?  If you:

  • Enjoy working in a high-volume call center.
  • Excel at providing timely, accurate answers via telephone by employing strong listening skills.
  • Enjoy new challenges and approach each day with a positive attitude.
  • Demonstrate a strong work ethic with a history of dependability and respect.
  • Possess excellent information retention capabilities.
  • Thrive in an environment that offers opportunities for continuous learning.

What will I gain from this role?

  • Gaining experience working in a call center environment.
  • Having the ability to work remotely from home.
  • Building in-depth communication and customer service skills.
  • Being a part of a fun, supportive team that offers great advancement opportunities throughout the organization.
  • Working in an environment that serves our Nation’s military, veterans, Guard and Reserves along with their families.

Minimum Qualifications

  • U.S. citizenship is required for this position due to Department of Defense restrictions.
  • Must live within the vicinity of our Madison, WI campus location (1717 W. Broadway in Madison, WI, 53713).
  • High school diploma or equivalent.
  • 2 or more years of experience in customer service (Call Center).
  • Ability to learn medical and insurance terminology.

Preferred Qualifications

  • Expertise in Microsoft Office (Outlook, Word, Excel), internet, intranet, office equipment, and data entry.
  • Ability to navigate dual monitor screens and between multiple programs at once.
  • Strong skillsets in multi-tasking, research, and problem-solving.
  • Ability to work independently, deescalate situations with agitated individuals, control difficult situations, as well as influence and motivate others to comply with TRICARE procedures.

Remote Work Requirements

  • Wired (ethernet cable) internet connection from your router to your computer
  • High speed cable or fiber internet
  • 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

  • Bargaining Unit position
  • Remote and hybrid work options available
  • Performance bonus and/or merit increase opportunities
  • 401(k) with dollar-per-dollar match up to 6% of 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/fulltime_benefits.shtml)

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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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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