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Evening Remote Health Insurance Jobs in Madison, WI

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Sales/Client Relations Specialist (FULLY REMOTE)

Madison, WI · Remote

$62K - $94K/yr

  • Medical

  • Dental

  • Vision

  • Life

  • PTO

100% Remote | Nationwide Opportunities We are expanding our remote team and looking for someone who ... Company Description We are a rapidly growing health insurance agency committed to helping ...

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Showing results 1-20

Evening Remote Health Insurance information

See Madison, WI salary details

$63K

$82.7K

$104.8K

How much do evening remote health insurance jobs pay per year?

As of Aug 19, 2026, the average yearly pay for evening remote health insurance in Madison, WI is $82,726.00, according to ZipRecruiter salary data. Most workers in this role earn between $74,600.00 and $85,600.00 per year, depending on experience, location, and employer.

What is an evening remote health insurance job?

Evening remote health insurance jobs are positions within the health insurance industry that allow employees to work from home or another remote location during evening hours. These roles can include customer service representatives, claims processors, case managers, or sales agents. They cater to individuals who prefer or require flexible schedules outside of the traditional 9-to-5 workday and often involve assisting customers, processing insurance claims, or providing support to policyholders. Working remotely in the evening can offer better work-life balance and accommodate different time zones or personal commitments.

What are some unique challenges faced when working as an evening remote health insurance representative?

Working as an evening remote health insurance representative often involves handling inquiries from clients who may need urgent assistance after standard business hours. This can mean managing higher-stress situations and working independently with less immediate support from supervisors. Additionally, maintaining clear communication with daytime team members is crucial to ensure smooth case handovers and consistent service. Adapting to varying customer needs and staying updated on changing policies can also be more challenging outside regular hours, making strong organizational and problem-solving skills essential.

What are the key skills and qualifications needed to thrive as an evening remote health insurance specialist, and why are they important?

To thrive as an Evening Remote Health Insurance Specialist, you need a solid understanding of health insurance policies, claims processing, and regulatory compliance, often supported by experience in the insurance industry or related certifications. Familiarity with insurance management software, CRM systems, and secure communication platforms is typically required. Strong attention to detail, excellent communication skills, and the ability to self-motivate while working independently are essential soft skills for this remote position. These skills ensure accurate policy handling, effective customer support, and maintain client trust during non-traditional working hours.

What is the difference between Evening Remote Health Insurance vs Evening Remote Medical Billing Specialist?

AspectEvening Remote Health InsuranceEvening Remote Medical Billing Specialist
CredentialsHealth insurance licenses, certifications (e.g., AHIP)Medical billing certifications (e.g., CPC, CBCS)
Work EnvironmentRemote, insurance companies, customer serviceRemote, healthcare providers, billing departments
Industry UsageInsurance industry, health plansHealthcare providers, hospitals, clinics
Common Search IntentInsurance coverage, plan inquiriesBilling processes, claim submissions

While both roles are remote and involve healthcare, Evening Remote Health Insurance focuses on insurance policies and customer support, whereas Evening Remote Medical Billing Specialist handles billing and claims processing for healthcare providers. Understanding these differences helps job seekers find the right position aligned with their skills and certifications.

What job categories do people searching Evening Remote Health Insurance jobs in Madison, WI look for?

The top searched job categories for Evening Remote Health Insurance jobs in Madison, WI are:

What cities near Madison, WI are hiring for Evening Remote Health Insurance jobs?

Cities near Madison, WI with the most Evening Remote Health Insurance job openings:

Infographic showing various Evening Remote Health Insurance job openings in Madison, WI as of August 2026, with employment types broken down into 87% Full Time, and 13% Contract. Highlights an 100% Remote job distribution, with an average salary of $82,726 per year, or $39.8 per hour.

Senior Account Manager - Health Insurance

WPS Health Solutions

Madison, WI • On-site, Remote

$85K - $105K/yr

Full-time

Medical, Dental, Life, Retirement, PTO

Posted 26 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 310 rated insurance


Job description

Role Snapshot
Our Senior Account Manager manages a book of mid-market and large employer groups (typically 250 – 1,000 lives), providing strategic guidance on benefit planning, renewal strategy, cost management, and member engagement. The Sr Account Manager will partner with the sales team to implement new employer groups and serve as the primary point of contact for ongoing support. They are accountable for developing and maintaining relationships with assigned employer group clients and identifying ways to drive growth and retention within our Health Plan.

Salary Range
$85,000 ~ $105,000
The base pay offered for this position may vary within the posted range based on your job-related knowledge, skills, and experience.
Remote work
Wisconsin - this position will have travel in the State of Wisconsin.
*As a secondary consideration, we could offer remote work in the following approved states:
Illinois, Iowa, Michigan, Minnesota.

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

  • Enjoy building and maintaining relationships with employer group leaders and broker partners to ensure retention year-to-year for assigned employer groups.
  • Have consulted with employer group accounts on plan benefits, performance data, and trends to identify opportunities for improvement, growth, and cross-selling.
  • Can lead complex renewals and present plan design recommendations.
  • Want to serve as a trusted advisor to employer group leaders and benefit decision-makers.
  • Would like to coordinate multi-product offerings (medical, dental, stop-loss, etc.) in support of a comprehensive benefit strategy.
  • Thrive when Partnering with Account Executives and underwriting on pricing strategies and negotiate renewals with employer group leaders and brokers.
  • Can proactively engage with clients through regular check-ins and provide benefit education to group leaders and members.
  • Want to serve as primary contact for client inquiries and service needs and ensure effective and timely resolution.
  • Can contribute to mentorship and knowledge-sharing across the sales and account management teams.
  • Would enjoy representing WPS at benefit fairs, board-level presentations, and broker strategy sessions.
  • Can maintain accurate CRM records and support sales growth opportunities.

Minimum Qualifications

  • Bachelor’s degree in Business, Marketing, Healthcare Administration or related field or equivalent combination of education/experience.
  • Valid Wisconsin Accident & Health producer license.
  • 5 or more years of progressive responsibility as an Account Manager or related experience.
  • Strong knowledge and understanding of health insurance benefit design.
  • Demonstrated experience in Health and Life Insurance Administration.
  • Excellent organizational, interpersonal, verbal and written communication skills this includes:
    • Strong problem-solving and workload prioritization skills.
    • Strong public speaking and presentation skills which include comfort in the presence of large audiences.
  • Ability to travel within the state of Wisconsin – up to 50%.
  • Valid driver’s license with no moving violations or accidents in the last three years.

Preferred

  • Self-Funded experience.
  • Experience using CRMs (i.e.: MS Dynamics, Salesforce).

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

  • 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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