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Insurance Sales Agent

Job in Milwaukee, Milwaukee County, Wisconsin, 53244, USA
Listing for: Webster Servicing LLC
Commission-based only position
Listed on 2026-08-17
Job specializations:
  • Sales
    B2B Sales, Insurance Sales
Salary/Wage Range or Industry Benchmark: 33062 - 35817 USD Yearly USD 33062.00 35817.00 YEAR
Job Description & How to Apply Below

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.
Salary

The estimated salary range for this position is $24.00

USD to $26.00

USD. Actual salary may vary up or down depending on job‑related factors such as knowledge, skills, experience, and location. In addition, this position is eligible for incentive compensation.

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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