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Evening Remote Health Insurance Jobs in Madison, WI

The McCrimmon Agency

Life Insurance Agent

Madison, WI · On-site +1

$30K - $160K/yr

This is a remote, commission-based opportunity for someone who values flexibility , personal growth ... Willing to obtain a Life & Health Insurance license in your state (if not already licensed)

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All JobsEvening Health Insurance JobsEvening Remote Health Insurance JobsEvening Remote Health Insurance Jobs in Madison, WI

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 Sep 9, 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 are popular job titles related to Evening Remote Health Insurance jobs in Madison, WI?

For Evening Remote Health Insurance jobs in Madison, WI, the most frequently searched job titles are:

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:

Evening Remote Health Insurance jobs near you
Infographic showing various Evening Remote Health Insurance job openings in Madison, WI as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 18% Part Time, 2% Temporary, and 5% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution, with an average salary of $82,726 per year, or $39.8 per hour.

Remote Insurance Sales Representative

Sun Prairie, WI • Remote

Dieter Insurance Group - Allstate Exclusive Agency
See more jobs at Dieter Insurance Group - Allstate Exclusive Agencyexternal

$60K - $150K/yr

Full-time

Medical, Retirement, PTO

Re-posted 23 days ago

Job description

Allstate Exclusive Agency

Looking for a career with unlimited earning potential and real growth opportunities?

Were hiring motivated, coachable sales professionals who enjoy helping people and want to build a successful insurance career. This is a fully remote W2 position for candidates who live in Wisconsin.

Already licensed? Great! If not, we can help qualified candidates obtain their Property & Casualty insurance license.

What We Offer

  • Base salary plus unlimited commission and bonuses
  • On-target earnings of $75,000+
  • Top performers can earn $150,000+
  • Paid training and mentorship
  • Health insurance
  • Paid time off
  • Retirement plan
  • MondayFriday schedule with evenings off
  • Career growth opportunities
  • Quality leads and live transfers


Who Were Looking For

  • Motivated, goal-oriented, and dependable
  • Coachable and eager to improve
  • Comfortable making a high volume of calls
  • Strong verbal and written communication skills
  • Customer-focused with an interest in sales
  • Able to work successfully in a remote team environment
  • High school diploma or equivalent


Hiring Process

  1. Quick phone interview
  2. Virtual interview
  3. Final interview


Our hiring process typically takes approximately one week.


Benefits

Annual Base Salary + Commission + Bonus Opportunities

Paid Time Off (PTO)

Health Insurance

Mon-Fri Schedule

Hands on Training

Career Growth Opportunities

Retirement Plan

Evenings Off


Responsibilities

What a Typical Day Looks Like

  • Make outbound calls to provided leads
  • Accept live transfers from prospects ready to discuss coverage
  • Follow up consistently with potential customers
  • Educate customers on the importance of proper insurance protection
  • Use real-life claim examples to explain coverage
  • Participate in daily sales training, practice, and coaching
  • Continue learning and developing your skills with the team
  • Help protect customers from everyday risks

Requirements
  • Educational Background: High School Diploma or equivalent is required.
  • Communication Abilities: Strong verbal and written communication skills to interact effectively with clients.
  • Sales Acumen: A keen interest in developing skills in sales and client relationship building.
  • Motivation: A self-starter with a positive attitude and the initiative to meet and exceed targets.
  • Customer Service: Ability to understand and address client needs effectively.
  • Adaptability: Willingness to learn about various insurance products and services offered by the company.
  • Team Participation: Ability to work collaboratively within a team-focused environment.

Please note -This is a position that requires an insurance license

Dont you have one? No problem- we can help you get one!

So, what are you waiting for?!?!

Hit the apply button and let's talk.