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Remote Insurance Sales Agent Jobs in Milwaukee, WI

HSA Bank

Insurance Sales Agent

Milwaukee, WI · Remote

$24 - $26/hr

The Individual Sales Agent is responsible for generating business through education, advisement ... In addition, this position is eligible for incentive compensation. #LI-BY1 #LI-REMOTE HSA Bank, a ...

The Long Agency

Life Insurance Sales Agent

Milwaukee, WI · On-site +1

$30K - $160K/yr

As a Life Insurance Sales Agent with the Long Agency, you will work with individuals and families who have requested information about life insurance coverage. This is a consultative sales role ...

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All JobsInsurance Sales Agent JobsRemote Insurance Sales Agent JobsRemote Insurance Sales Agent Jobs in Milwaukee, WI

Remote Insurance Sales Agent information

See Milwaukee, WI salary details

$27.1K

$71.4K

$137.4K

How much do remote insurance sales agent jobs pay per year?

As of Aug 23, 2026, the average yearly pay for remote insurance sales agent in Milwaukee, WI is $71,389.00, according to ZipRecruiter salary data. Most workers in this role earn between $46,800.00 and $88,200.00 per year, depending on experience, location, and employer.

What does a remote insurance sales agent do?

A Remote Insurance Sales Agent sells insurance policies to clients over the phone, email, or video calls instead of in person. They assess customer needs, provide policy information, answer questions, and help clients choose the best coverage options. Working remotely allows them to serve clients from different locations and often provides flexible work hours. They may work for insurance companies, brokers, or as independent agents, and are typically responsible for meeting sales goals and maintaining client relationships.

What are the key skills and qualifications needed to thrive as a remote insurance sales agent?

To thrive as a Remote Insurance Sales Agent, you need strong sales acumen, knowledge of insurance products, and typically a valid insurance license. Familiarity with CRM software, online quoting platforms, and e-signature tools is essential for managing leads and streamlining the sales process. Outstanding communication, self-motivation, and resilience help agents connect with clients and succeed in a remote environment. These skills and attributes are crucial for building trust, closing sales, and maintaining productivity without in-person supervision.

What are some common challenges faced by remote insurance sales agents and how can they be managed?

Remote insurance sales agents often face challenges such as building trust with clients virtually, managing their own schedules, and staying motivated without in-person supervision. To overcome these obstacles, agents can leverage video conferencing tools to create personal connections, set clear daily and weekly goals, and participate in regular team meetings for support and accountability. Many organizations also provide ongoing training and digital resources to help remote agents stay connected and successful.

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

AspectRemote Insurance Sales AgentRemote Insurance Underwriter
Required CredentialsLicenses (e.g., state-specific insurance license), sales experienceUnderwriting certifications, insurance knowledge
Work EnvironmentRemote, client-facing, sales-focusedRemote, analytical, review-based
Employer & Industry UsageInsurance agencies, brokers, carriersInsurance companies, underwriting firms
Common Search & ComparisonSales roles, licensing, client interactionRisk assessment, policy evaluation

The main difference is that Remote Insurance Sales Agents focus on selling insurance policies and interacting directly with clients, often requiring sales licenses. In contrast, Remote Insurance Underwriters evaluate risks and determine policy terms, requiring underwriting certifications. Both roles are remote and industry-specific but serve different functions within the insurance sector.

Are remote insurance sales jobs legit?

Remote insurance sales agent positions are legitimate roles within the insurance industry that involve selling policies online or over the phone. These jobs often require licensing, strong communication skills, and familiarity with sales tools, and they can be full-time or part-time employment. However, job seekers should verify the employer's credibility to avoid scams.

Do remote insurance sales agents work from home?

Remote insurance sales agents typically work from home or a personal office environment, using digital communication tools like phone, email, and video conferencing to connect with clients. They often have flexible schedules but may need to meet sales targets and complete required training or certifications. The role relies on strong communication skills and familiarity with sales software.

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

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

What are popular job titles related to Remote Insurance Sales Agent jobs in Milwaukee, WI?

For Remote Insurance Sales Agent jobs in Milwaukee, WI, the most frequently searched job titles are:

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

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

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

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

Remote Insurance Sales Agent jobs near you
Infographic showing various Remote Insurance Sales Agent job openings in Milwaukee, WI as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% Remote job distribution, with an average salary of $71,389 per year, or $34.3 per hour.

Insurance Sales Agent

HSA Bank

Milwaukee, WI • Remote

$24 - $26/hr

Full-time

Re-posted 18 days ago

Job description

At HSA Bank, a division of Santander Bank N.A., 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


HSA Bank, a division of Santander Bank, N.A.Santander Holdings USA, Inc. and its subsidiaries ("Santander") are equal opportunity employers 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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