Insurance Sales Agent

Webster Servicing LLC

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WI Milwaukee Erie St Remote-Nationwide remote Until 8/23/2026 0+ years exp First posted June 5, 2026 Last posted June 5, 2026
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.

About this role

Summary

Generate insurance sales through education, advisement, and enrollment via tele sales.

Job title

Insurance Sales Agent

Experience level

0-2 years

Minimum experience

0+ years exp

Industry

healthcare

Location requirements

Remote work nationwide, based in Wisconsin Milwaukee

Salary

$24k–$26k

Management role

No

Skills & keywords

Required skills

insurance productssalesCRMpresentation

Preferred skills

group health plansB2BB2B2C

Specializations

insurancemedicarehealth planssalestele sales
Locations

Structured locations inferred from the posting.

Milwaukee, WI, USA

Remote City