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Remote Group Insurance Sales Jobs in Wisconsin (NOW HIRING)

HSA Bank

Insurance Sales Agent

Milwaukee, WI · Remote

$24 - $26/hr

... Group Insurance, Individual and Family Plans, and Ancillary products. * Sales Skill - Familiarity ... In addition, this position is eligible for incentive compensation. #LI-BY1 #LI-REMOTE Webster ...

The Summers Group

Life Insurance Sales Agent

Milwaukee, WI · On-site +1

$30K - $160K/yr

As a partner agency within Symmetry Financial Group, our agents have access to industry leading ... No prior experience in sales or insurance is required. Core Responsibilities: * Consult with ...

The Long Agency

Life Insurance Sales Agent

Madison, WI · On-site +1

$30K - $160K/yr

The Long Agency, within Symmetry Financial Group, is growing and looking for driven individuals who ... No prior sales or insurance experience is required. Position Overview : As a Life Insurance Sales ...

The Long Agency

Life Insurance Sales Agent

Milwaukee, WI · On-site +1

$30K - $160K/yr

The Long Agency, within Symmetry Financial Group, is growing and looking for driven individuals who ... No prior sales or insurance experience is required. Position Overview : As a Life Insurance Sales ...

Comparion Insurance Agency

$56K - $65K/yr

Sales - Comparion Description Comparion Insurance Agency is hiring self-motivated, relationship ... Flexible work structure (hybrid office, field, and remote based on what your day requires)

New

Comparion Insurance Agency

$56K - $65K/yr

Sales - Comparion Description Comparion Insurance Agency is hiring self-motivated, relationship ... Flexible work structure (hybrid office, field, and remote based on what your day requires)

New

Comparion Insurance Agency

$56K - $65K/yr

Sales - Comparion Description Comparion Insurance Agency is hiring self-motivated, relationship ... Flexible work structure (hybrid office, field, and remote based on what your day requires)

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Showing results 1-20

All JobsGroup Insurance Sales JobsRemote Group Insurance Sales JobsRemote Group Insurance Sales Jobs in Wisconsin

Remote Group Insurance Sales information

What is a remote group insurance sales professional?

A Remote Group Insurance Sales job involves selling group insurance policies—such as health, life, or disability insurance—to organizations and businesses while working from a remote location. Professionals in this role identify prospective clients, explain plan options, and assist companies in selecting coverage that best fits their employees’ needs. The job typically includes tasks like virtual meetings, digital presentations, and ongoing client support, all managed from a home office or other remote setting. Strong communication skills, sales experience, and knowledge of insurance products are essential for success in this career.

What skills and qualifications are needed to thrive as a remote group insurance sales professional?

To thrive as a Remote Group Insurance Sales professional, you need strong sales acumen, a solid understanding of insurance products, and typically a valid insurance license. Proficiency with CRM software, virtual communication platforms, and quoting systems is essential for managing leads and client interactions remotely. Excellent communication, self-motivation, and relationship-building skills help you stand out in a competitive market. These skills and qualities are crucial for effectively reaching clients, closing deals, and maintaining long-term business relationships from a remote setting.

How does a remote group insurance sales professional typically collaborate with underwriters and client services teams?

As a remote group insurance sales professional, you’ll regularly collaborate with underwriters to assess risk, develop customized proposals, and ensure coverage aligns with client needs. You’ll also coordinate with client services teams to address policy changes, manage renewals, and resolve customer inquiries. Effective communication through virtual meetings and digital collaboration tools is key, as these partnerships are essential for delivering seamless service and closing sales. Building strong internal relationships helps streamline processes and enhances the client experience.

What is the difference between Remote Group Insurance Sales vs Remote Insurance Agent?

AspectRemote Group Insurance SalesRemote Insurance Agent
CredentialsLicenses in health/life insurance, sales experienceLicenses in health/life insurance, sales experience
Work EnvironmentPrimarily remote, focused on B2B salesPrimarily remote, B2C and B2B sales
Employer & IndustryInsurance companies, brokers, agenciesInsurance companies, brokers, agencies
Search & Comparison IntentUnderstanding B2B sales roles in insuranceUnderstanding B2C and B2B insurance sales roles

Remote Group Insurance Sales focuses on selling group insurance plans to organizations, often involving B2B interactions. Remote Insurance Agents typically sell individual policies directly to consumers. While both roles require insurance licenses and sales skills, their target clients and sales approaches differ, making the comparison useful for job seekers exploring different insurance sales careers.

Are remote group insurance sales jobs legit?

Remote group insurance sales jobs are legitimate roles in the insurance industry that involve selling group coverage plans remotely, often requiring strong communication skills and knowledge of insurance products. However, job seekers should verify the employer's credibility and be cautious of scams that may request upfront payments or personal information. Conducting research and reviewing company reviews can help ensure the job's legitimacy.

What are popular job titles related to Remote Group Insurance Sales jobs in Wisconsin?

For Remote Group Insurance Sales jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Remote Group Insurance Sales jobs in Wisconsin look for?

The top searched job categories for Remote Group Insurance Sales jobs in Wisconsin are:

What cities in Wisconsin are hiring for Remote Group Insurance Sales jobs?

Cities in Wisconsin with the most Remote Group Insurance Sales job openings:

Remote Group Insurance Sales jobs near you
Infographic showing various Remote Group Insurance Sales job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 20% Part Time, and 5% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution.

Insurance Sales Agent

HSA Bank

Milwaukee, WI • Remote

$24 - $26/hr

Full-time

Re-posted 15 days ago

Job description

At HSA Bank, we're working toward a world where everyone is empowered to save for a healthy future. Our offerings in the healthcare savings space drive down healthcare costs, increase access, and assist with decision-making for consumers, health plans, partners, and advisors.


Are you ready to join us?

The Individual Sales Agent is responsible for generating business through education, advisement, and enrollment of Webster consumers in plans such as Medicare Supplement, Medicare Advantage, ACA, Hospital Indemnity, Critical Illness, and other individual or family insurance products through outbound and inbound tele sales. This role reports to the Managing Director of Medicare Sales and requires the ability to discuss these plans in detail and then confidently make a recommendation to complete the enrollment while using the necessary tools such as softphones, quoting tools, and other web-based items.

What you will do

  • Product Knowledge - Strong working knowledge of insurance products like Medicare Supplement, Medicare Advantage, Group Insurance, Individual and Family Plans, and Ancillary products.

  • Sales Skill - Familiarity selling in DTC, B2B, and B2B2C setting.

  • Presentation Skills - Create and present compelling demonstrations of services to prospective clients, highlighting benefits and value propositions.

  • Ability to multi-task - IE navigate several computer screens while having a discussion with consumers.

  • Sales Cycle Knowledge - Ability to educate, recommend, close, and service business through the entire sales life cycle.

  • Documentation - Must be able to use internal tools like CRMs and quoting tools to document and track current and potential business for analysis and use by other organizational stakeholders.


Skills and Abilities

  • A desire to compete and comfort working on a commission-based salary.


Education Qualifications

  • H.S. Diploma or General Education Degree (GED) required

  • Bachelor's Degree in Arts/Sciences (BA/BS) preferred


Experience Qualifications

  • 0-2 years Medicare or ACA focused sales role required

  • 0-2 years Working with group health plans preferred

  • 0-2 years Selling B2B or B2B2C required


Licenses and Certifications

  • Life and Health license with the ability to be licensed in other non-resident states upon hire required

The estimated salary range for this position is $24.00USD to $26.00USD. Actual salary may vary up or down depending on job-related factors which may include knowledge, skills, experience, and location. In addition, this position is eligible for incentive compensation.

#LI-BY1

#LI-REMOTE

Webster Financial Corporation and its subsidiaries ("Webster") are equal opportunity employers that are committed to sustaining an inclusive environment. All qualified applicants will receive consideration for employment without regard to race, color, religion, age, marital status, national origin, ancestry, citizenship, sex, sexual orientation, gender identity and/or expression, physical or mental disability, protected veteran status, or any other characteristic protected by law.

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