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

Harmony Health Plans Inc

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Licensed Health Insurance Agents (1099) Remote

Milwaukee, WI · Remote

$5.0K - $25K/mo

Health insurance industry knowledge * Effective sales techniques and customer relationship management (CRM) skills * Understanding of compliance and regulatory standards * Strong self-motivation and ...

Globe Life American Income Division

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Remote Insurance Sales Associate

Milwaukee, WI · Remote

$50K - $120K/yr

... 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 ...

Pioneer Agency

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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All JobsHealth Insurance JobsRemote Health Insurance JobsRemote Health Insurance Jobs in Milwaukee, WI

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 Jul 26, 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 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 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 remote health insurance jobs?

Remote health insurance jobs are positions within the health insurance industry that can be performed from home or any location outside of a traditional office. These roles include customer service representatives, claims processors, underwriters, and sales agents, among others. Employees use digital tools to handle tasks such as assisting policyholders, processing claims, or reviewing applications. Remote health insurance jobs offer flexibility and can often be found with major insurance companies or third-party administrators. These positions typically require strong communication skills, proficiency with computers, and knowledge of healthcare regulations.

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 Remote Jobs Working in Health Insurance?

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.

More about Remote Health Insurance jobs
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 are popular job titles related to Remote Health Insurance jobs in Milwaukee, WI? For Remote Health Insurance jobs in Milwaukee, WI, the most frequently searched job titles 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:
Remote Health Insurance jobs near you
Infographic showing various Remote Health Insurance job openings in Milwaukee, WI as of July 2026, with employment types broken down into 100% Full Time. Highlights an 100% Remote job distribution, with an average salary of $80,888 per year, or $38.9 per hour.
Remote ACA Health Insurance Seasonal Sales Agent

Remote ACA Health Insurance Seasonal Sales Agent

Thrive Health Benefits

Milwaukee, WI • Remote

$768 - $1.3K/wk

Temporary

Posted 3 days ago

Job description

Thrive Health Benefits is hiring Remote ACA Sales Agents to support Open Enrollment. This is a seasonal, W-2 position (standard payroll withholding — not a 1099 contract) for candidates who are licensed, or in the process of becoming licensed, to sell health insurance in Florida, Texas, and Georgia.
Agents handle inbound calls and warm transfers to help individuals and families enroll in ACA Marketplace health plans. No cold calling or lead generation is required. With ten years of specialization in the ACA Marketplace, Thrive Health Benefits provides full training on sales processes, systems, and compliance prior to taking live calls.
What You'll Do
• Work 100% remote, handling inbound calls and live transfers — no cold calling
• Assist individuals and families with ACA Marketplace plan enrollment
• Follow approved, CMS-compliant scripts and sales processes
• Accurately assess client needs and recommend appropriate plan options
• Maintain compliance standards on every call
• Meet weekly production and quality expectations during Open Enrollment
Schedule
This is a fixed, seasonal sprint running through December 15. During Open Enrollment (November 1 – December 15), the schedule requires 50 hours across 6 days per week, including the Thanksgiving holiday week, with no time off during this window. Candidates should confirm availability for this schedule before applying.
Why Thrive Health Benefits
• ACA Marketplace is our sole focus — 10 years of specialization in a fast-growing space
• Full training on sales, systems, and compliance provided before taking live calls
• Top-performing seasonal agents may be considered for permanent roles

Requirements

What You Need
• Active Errors & Omissions (E&O) insurance
• Active health insurance producer license(s) — one of the following applies:
- Fully licensed: active resident or non-resident producer licenses in Florida, Texas, and Georgia (may begin immediately)
- Partially licensed: active resident (home-state) producer license and E&O insurance required to apply. Candidates who advance through the interview process receive a conditional offer with step-by-step guidance to obtain the remaining state licenses independently (typical cost ~$375, 7–14 business days). Thrive Health Benefits reimburses $750 upon completion of licensing (paid after license is obtained, not upfront).
• If currently appointed with another carrier or agency, must be able to release and transfer that appointment prior to start (standard regulatory requirement)
• Reliable computer and hardwired Ethernet internet connection
• Ability to commit to the full Open Enrollment schedule (50 hrs/6 days per week, Nov 1 – Dec 15, including Thanksgiving week)

Benefits

What You'll Earn
• Base pay: $24.00/hour during a 32-hour/week ramp-up period
• Open Enrollment period (Nov 1 – Dec 15): scheduled hours increase to 50/week (including overtime), bringing base earnings to approximately $1,320/week before commission
• Weekly commission, paid per enrollment on a tiered scale:
- 31–50 applications: $8 each
- 51–75 applications: $12 each
- 76–100 applications: $14 each
- 101+ applications: $16 each
• Additional income opportunities from ancillary product sales and referrals
• Illustrative earning potential: consistent, high-performing agents have earned $13,000+ over the six-to-seven-week Open Enrollment period (illustrative only, based on individual performance, not guaranteed)
• Growth opportunity: top-performing seasonal agents may be considered for permanent roles
Note: Earnings figures listed above are illustrative examples based on individual performance and are not guaranteed.

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