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Remote Health Insurance Jobs in Milwaukee, WI (NOW HIRING)

Full licensing support -- we walk you through getting your Life and Health Insurance License (most ... Raleigh/Triangle area preferred -- fully remote, open to all U.S. locations * Able to pass a ...

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... life and health supplemental insurance benefits to working-class families in the United States ... We are currently seeking a Remote Associate to join our team! Please note that we can only hire ...

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Harmony Health is partnering with licensed health agents nationwide to sell ACA Marketplace plans ... insurance. Don't have all three yet? Get started anyway and we'll show you how. - A reliable ...

Insurance Agent

Milwaukee, WI · On-site +1

$30K - $160K/yr

Remote work and in-person training opportunities available * Potential to earn a raise every 2 months Health insurance available Earn equity in the company Opportunity to own your own agency (if ...

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Remote Sales/Customer Service Representative

Milwaukee, WI · Remote

$58K - $194K/yr (+ commission)

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 ...

Life Insurance Agent

Milwaukee, 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)

Insurance Agent

Milwaukee, WI · Remote

$50K - $75K/yr

Present and recommend a range of insurance products, including Life, Health, and Retirement options ... Remote work opportunities with flexible scheduling to fit your lifestyle. * Competitive commission ...

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Showing results 1-20

Remote Health Insurance information

See Milwaukee, WI salary details

$61.6K

$80.9K

$102.5K

How much do remote health insurance jobs pay per year?

As of Sep 1, 2026, the average yearly pay for remote health insurance in Milwaukee, WI is $80,888.00, according to ZipRecruiter salary data. Most workers in this role earn between $72,900.00 and $83,700.00 per year, depending on experience, location, and employer.

What are remote health insurance jobs?

Remote health insurance jobs involve working in sales or providing customer service to policy-holders. As a work-from-home insurance agent, you sell healthcare policies to customers. You communicate with each customer by phone or internet to define their coverage needs, then help them select an insurance plan that has the benefits to meet those needs. Your duties can include assisting clients as they complete paperwork to obtain coverage and answering questions from new or existing policy-holders.

What are some common challenges of working in a remote health insurance role, and how can they be managed?

A common challenge in remote health insurance roles is maintaining effective communication with both clients and team members, as much of the work relies on virtual interactions. To manage this, professionals often use secure digital platforms and regularly scheduled video meetings to stay connected. Another challenge is staying updated with changing regulations and insurance policies, which requires proactive participation in ongoing training and close collaboration with compliance teams. Time management and self-motivation are also crucial, as remote work requires balancing multiple tasks independently throughout the day.

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

To thrive as a Remote Health Insurance Specialist, you need a solid understanding of health insurance policies, claims processing, and regulatory compliance, often supported by a relevant degree or insurance license. Familiarity with CRM software, claims management systems, and digital communication tools is typically required. Strong attention to detail, problem-solving skills, and effective virtual communication set top performers apart. These skills ensure accurate claim handling, regulatory adherence, and excellent customer service in a remote work environment.

What is the difference between Remote Health Insurance vs Remote Medical Claims Processor?

AspectRemote Health InsuranceRemote Medical Claims Processor
Required CredentialsInsurance licenses, knowledge of health policiesMedical billing certifications, claims processing knowledge
Work EnvironmentHome-based, insurance companies or brokersHome-based, healthcare providers or insurance companies
Industry UsageInsurance industry, health plansHealthcare providers, insurance companies
Common Search/ComparisonRemote health insurance vs remote medical claims processor

Remote Health Insurance professionals focus on selling, managing, or advising on health insurance policies, often requiring licensing and industry knowledge. Remote Medical Claims Processors handle the review and processing of medical claims, typically needing billing certifications. Both roles are home-based and serve the healthcare and insurance sectors, but they differ in responsibilities and credentials.

What are the most commonly searched types of Health Insurance jobs in Milwaukee, WI?

The most popular types of Health Insurance jobs in Milwaukee, WI are:

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

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

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

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

Infographic showing various Remote Health Insurance job openings in Milwaukee, WI as of August 2026, with employment types broken down into 63% Full Time, 5% Temporary, and 32% Contract. Highlights an 100% Remote job distribution, with an average salary of $80,888 per year, or $38.9 per hour.

$24/hr Remote Health Agents + OT + Weekly Commissions

Thrive Health Benefits

Milwaukee, WI • Remote

$768 - $1.3K/wk (+ commission)

Temporary

Re-posted 10 days ago


Job description

$24/hr hour. Overtime during Open Enrollment. Weekly commission on every enrollment. We’re hiring high performing remote ACA agents who want a season of serious income, reliable hours, and a team that actually supports you. This is a seasonal W 2 role — real paycheck, taxes handled, no 1099 headaches.


You can start as early as September 8, and Open Enrollment runs November 1 – January 15. This is a four and a half month earning season, not a short six week gig.


What You’ll Earn

· Start as early as September 8 – $24/hour base, about 32 hours/week during training and ramp up (roughly $768/week)

· Open Enrollment: November 1 – January 15 – 50 hours/week, overtime at $36/hour past 40 (about $1,320/week in base pay alone) + weekly commissions

· Overtime rules follow your state’s laws — we’ll confirm your exact eligibility before your first shift

· Roughly $20,200 in guaranteed base pay from Sept 8 – Jan 15, before a dollar of commission

· Commission paid weekly on every enrollment — the more you write, the more you earn

· Additional income from ancillary products + referrals

· Strong producers routinely clear $27,000+ across the full season (illustrative, based on consistent production)


Earn Before Open Enrollment Even Starts

· $300 for every agent you refer Know a licensed agent? A friend? Former co worker? Bring them to our hiring webinar. If they’re hired and both of you finish the season, you earn $300 per agent. Refer three = $900 extra before OE even begins.


What You’ll Do

· Work 100% remote, from home · Help inbound callers and live transfers enroll in ACA Marketplace plans — no cold calling · Follow proven, compliant scripts with full training, coaching, and support · Focus on helping families find coverage they can actually afford — and get paid properly for doing it.


What You Need

· Active E&O insurance · Resident or non resident licenses in FL, TX, and GA

Don’t have all three yet? Apply anyway. If you pass the interview, you’ll receive a conditional offer with exact steps to get licensed — and we reimburse up to $375 based on the licenses you obtain (paid after you’re licensed).

Already licensed in FL/TX/GA? You can start immediately.

· A reliable computer and a wired Ethernet connection


Heads Up – Open Enrollment Is a Sprint

November 1 – January 15 is 50 hours/week across 6 days, with no vacation during the window. Eleven weeks, all in — and worth it.


Ready to Earn? Apply Now.

The earlier you’re set up, the sooner you start earning. Base pay of $24/hour is guaranteed for hours worked. Overtime is paid at $36/hour where state law provides for it; overtime rules vary by state. Commission, bonus, and total season figures are illustrative and based on individual performance.