Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Licensed Health Insurance Agent (Ancillary Products)

$40k - $70k
Full-time

Pitch Health Solutions

Licensed Health Insurance Agent (Ancillary Products) – W2 + Commission | Remote

Company: Pitch Health
Location: Remote (U.S. Only)
Compensation: Hourly Base + Commission + Performance Incentives ($40,000–$70,000/year OTE )
Employment Type: Full-Time (W-2)

Overview
Pitch Health is hiring licensed health insurance agents to sell ancillary products including hospital indemnity, critical illness, and cancer plans. This is a W-2 position with hourly pay plus uncapped commission, designed for agents who want consistent income + strong upside in a structured, high-performance environment.

What You'll Be Doing

  • Handle inbound calls from pre-qualified prospects (no cold calling)
  • Educate clients on coverage options: Hospital Indemnity, Critical Illness, Cancer Insurance
  • Identify needs, overcome objections, and close sales
  • Complete enrollments accurately and compliantly
  • Maintain performance metrics (sales, talk time, compliance)

Compensation Structure

  • Hourly Base Pay (W-2)
  • Uncapped Commission per Policy Sold
  • Performance Bonuses & Incentives

High performers benefit from consistent inbound volume, strong close rates, and daily production opportunities.

What We Provide

  • Inbound Call Flow – No self-generated leads
  • Warm Transfers – High-intent prospects ready to talk
  • Structured Sales System – Scripts, training, and proven frameworks
  • Daily Coaching & Support – Real-time feedback
  • Clear KPIs – Defined expectations for success
  • Growth Path – Opportunities into Team Lead and leadership roles

Requirements

  • Active Health Insurance License (Required)
  • Prior experience in Medicare or ancillary sales preferred
  • Strong closing ability and objection handling
  • Comfortable working in a metric-driven environment
  • Reliable internet and remote work setup

Success Profile
You'll thrive here if you want stable base pay + high earning potential, perform well in high-volume inbound sales environments, are competitive, coachable, and results-driven, and can follow a system and execute daily.

This Role Is NOT For

  • Agents looking for part-time or passive income
  • Individuals uncomfortable with performance expectations
  • Those unwilling to follow structure or coaching

Why Pitch Health
We've built a system that removes the hardest parts of sales—lead generation and guesswork—so you can focus on what matters: closing deals and making money.

Vacancy posted 4 days ago
Similar jobs that could be interesting for youBased on the Licensed Health Insurance Agent (Ancillary Products) in Chicago, IL vacancy
  • $45k - $100k

     ...credit unions, and associations. We are licensed in 49 states, the District of Columbia...  ...Conventions and incentive trips Production awards Advancement based on performance...  ...Lifetime renewals Benefits (Health Insurance, Life Insurance) Union backed contract... 
    Health Insurance
    Weekly pay
    Contract work
    Remote work
    Work from home
    Flexible hours

    Millennium Recruiting, Inc.

    Chicago, IL
    4 days ago
  • $24 - $29 per hour

     ...Licensed Health Insurance Enrollment Specialist We are recruiting Licensed Health Insurance Agents on behalf of a cutting-edge, venture-backed health technology company. Their platform enables modern companies to transition away from traditional group health plans... 
    Health Insurance
    Full time
    Seasonal work
    Immediate start
    Remote work
    Home office
    Monday to Friday
    Flexible hours
    Shift work
    Weekend work
    Weekday work

    Medix

    Chicago, IL
    3 days ago
  • $18 per hour

     ...committed to offering a reputable product suite that protects people...  ...dreams. As a full-time Insurance Sales Representative, you will...  ...Allstate's discretion. Eligible licensed external candidates who...  ...starting day one , including: ~ Health, dental, and vision insurance... 
    Health Insurance
    Hourly pay
    Minimum wage
    Full time
    Contract work
    Work at office
    Local area
    Remote work
    Work from home
    Home office
    Work visa
    Afternoon shift

    Allstate Insurance Company

    Chicago, IL
    3 days ago
  • $18 per hour

     ...Insurance Sales Representative At Allstate, great things happen...  ...committed to offering a reputable product suite that protects people...  ...Allstate's discretion. Eligible licensed external candidates who...  ...starting day one, including: ~ Health, dental, and vision insurance... 
    Health Insurance
    Remote job
    Hourly pay
    Minimum wage
    Full time
    Work at office
    Local area
    Work from home
    Home office
    Work visa
    Afternoon shift

    Allstate

    Chicago, IL
    1 day ago
  •  ...while thousands of experienced agents are retiring each year—...  ...requested information about life insurance. Conduct professional needs...  ...experience required. ✔️ Licensing assistance provided. ✔️ Experienced...  .... Income varies based on production and performance. Next... 
    Suggested
    Remote work
    Flexible hours

    The Bill Lampe Group Inc.

    Chicago, IL
    1 day ago
  •  ...while thousands of experienced agents are retiring each year—...  ...requested information about life insurance. Conduct professional needs...  ...experience required. Licensing assistance provided. Experienced...  .... Income varies based on production and performance. Next... 
    Remote work
    Flexible hours

    The Bill Lampe Group Inc.

    Chicago, IL
    4 days ago
  •  ...industry right now. The life insurance space is shifting fast....  ...coverage. A wave of veteran agents is heading into retirement. And...  ...in sales — any industry, any product Communicate clearly and build...  ...system Are willing to get licensed (we'll help) Are looking for... 
    Remote work
    Shift work

    PSI Groups

    Chicago, IL
    2 days ago
  •  ...matching Company parties Dental insurance Flexible schedule Health insurance Opportunity for...  ...to add a new Insurance Agent to our team. We are a...  ...Earnings are based on individual production and performance. Potential...  ...to Obtain State Insurance License College Degree (preferred,... 
    Health Insurance
    Work at office
    Local area
    Work from home
    Flexible hours

    Boyle Region - Modern Woodmen of America

    Oak Park, IL
    3 days ago
  •  ...an Integrity Marketing Partner, is hiring Licensed Individuals ready to take their business to the next level in the Life Insurance and Financial Services Industry . We’re looking...  ...life insurance solutions Present products confidently (virtual or in-person) Build... 
    Remote work
    Flexible hours

    PSI Groups

    Chicago, IL
    5 days ago
  •  ...of Nicole Page - State Farm Agent. As a member of our agency...  ...community to promote State Farm products including auto, home and life insurance. This position will allow...  ...Property and Casualty license (must be able to obtain) Life and Health license (must be able to obtain... 
    Health Insurance
    For contractors
    Work at office

    State Farm

    Chicago, IL
    5 days ago
  •  ...while thousands of experienced agents are retiring each year—...  ...requested information about life insurance. \n Conduct professional needs...  ...experience required. \n ✔️ Licensing assistance provided. \n ✔️...  ...\n Income varies based on production and performance. \n \n... 
    Remote work
    Flexible hours

    The Bill Lampe Group Inc.

    Chicago, IL
    15 days ago
  •  ...are dedicated providers of tailored insurance solutions for a variety of clients, including...  ...is a full-time remote role for a Licensed Insurance Agent. The Licensed Insurance Agent will...  ...Brokerage Strong knowledge of Insurance products and general Finance principles... 
    Full time
    Remote work

    Choiceplusis.com & Petbusinessinsurance.com

    Chicago, IL
    2 days ago
  •  ...Licensed Life Insurance Agent | Remote | Living Benefits & Uncapped Earnings Performance-Based | Daily...  ...Group provides access to competitive products, industry-leading carriers, proven...  ...organization behind you. OPTIONAL HEALTH BENEFITS Our optional Integrity Health... 
    Health Insurance
    Daily paid
    For contractors
    Remote work
    Flexible hours

    The Weiner Group Defunct

    Chicago, IL
    2 days ago
  •  ...State Farm Agent Team MemberDo you have aspirations to run...  ...community to promote State Farm products including auto, home and life insurance. This position will allow...  ...and Casualty license (must be able to obtain)Life and Health license (must be able to obtain... 
    Health Insurance
    For contractors
    Work at office

    Nicole Page - State Farm Agent

    Chicago, IL
    2 days ago
  •  ...State Farm Agent Team Member Do you have aspirations to...  ...community to promote State Farm products including auto, home and life insurance. This position will allow...  ...Property and Casualty license (must be able to obtain) Life and Health license (must be able to obtain... 
    Health Insurance
    For contractors
    Work at office

    Nicole Page - State Farm Agent

    Chicago, IL
    2 days ago
  •  ...Farm independent contractor agent may be the career for you...  ...market only State Farm insurance and financial service products. Responsibilities...  ...plus commission/bonus Health benefits Paid time off...  ...complete any applicable licensing requirements and training... 
    Health Insurance
    Hourly pay
    For contractors
    Bank staff
    Work at office

    Nicole Page - State Farm Agent

    Chicago, IL
    5 days ago
  •  ...Illinois Paid Time Off, Health Insurance, Dental Insurance, Vision Insurance...  ...individuals to join its Agent Apprentice Program, a unique...  ...& Casualty Insurance License through the sponsored licensing...  ...Renters, Umbrella Insurance products Build and strengthen customer... 
    Health Insurance
    Remote job
    Apprenticeship

    FX Insurance Agency LLC

    Chicago, IL
    4 days ago
  •  ...The Insurance Representative is directly responsible for...  ...number of submitted life & health applications, life and...  ...and health insurance license is required. Valid...  ...employee? Career Agency agents and managers meet client needs by providing products and services that are... 
    Health Insurance
    Immediate start
    Weekend work
    Afternoon shift

    Transamerica Agency Network

    Chicago, IL
    3 days ago
  • $30k - $52k

     ...Plageman Agency Inc. , you’ll sell insurance the way we believe it should be sold...  ...have hands-on training, mentorship, licensing assistance, PTO, health, dental, and vision insurance, and a...  ...weekly networking group. Cross-sell products across all insurance lines. Build relationships... 
    Health Insurance

    The Juris Agency

    Chicago, IL
    5 days ago
  •  ...Job Description The Frances Wright Insurance Agency is looking for Licensed P&C (Property & Casualty) and Life Insurance Agent, where your expertise will empower clients to secure...  ...life, property, and casualty insurance products. Manage sales administration tasks using systems... 
    Flexible hours

    The Juris Agency

    Chicago, IL
    1 day ago
  •  ...As a Licensed Insurance Sales Representative, you will help individuals through...  ...of selecting a Medicare health insurance plan that matches...  ...available to all of our licensed agents. Not a licensed agent? Not a...  ...health insurance plans and products to our customers. Outbound... 
    Health Insurance
    Temporary work
    Monday to Friday
    Shift work

    OneDigital Advanced Health

    Chicago, IL
    1 day ago
  • $30k - $160k

     ...Own your future and launch your agent career today. Unsure of joining the insurance industry? Our agents have transitioned...  ...to obtain a life insurance license (with our help) if not already licensed...  ...with exclusive digital insurance products, revolutionary insurtech, a... 
    Full time
    Part time
    For contractors
    Remote work

    Symmetry Financial Group

    Chicago, IL
    12 days ago
  • $30k - $160k

     ...within Symmetry Financial Group, our agents have access to industry leading insurance carriers, innovative technology,...  ...: • A current life insurance license and NPN • A strong, coachable...  ...No agent’s success, earnings, or production results should be viewed as typical... 
    Full time
    Part time
    For contractors
    Summer work

    The Summers Group

    Chicago, IL
    more than 2 months ago
  •  ...comprehensive training to become a true product expert before you ever make a call, and...  ...results. Benefits Paid Time Off (PTO) Health Insurance Retirement Plan Tuition Reimbursement Hands...  ...We Invest In You We Help With Getting Licensed Warm Leads Provided Responsibilities... 
    Health Insurance
    Day shift

    The Juris Agency

    Chicago, IL
    5 days ago
  •  ...a growing, community-focused insurance agency committed to providing...  ...Benefits Paid Time Off (PTO) Health Insurance Retirement Plan Flexible...  ...close sales and meet monthly production goals. Build strong customer...  ...Illinois Property & Casualty License preferred but not required.... 
    Health Insurance
    Work at office
    Flexible hours

    The Juris Agency

    Elmwood Park, IL
    4 days ago
  • $75k

     ...Outbound Insurance Sales Specialist Remote | Full-Time Are you an experienced P&C insurance agent who prefers outbound sales over sitting in an inbound call queue? We...  ...employment ~ Remote work ~ Company-supported licensing expansion across all 50 states ~ Clear... 
    Full time
    Remote work

    Clear Point Consultants

    Chicago, IL
    1 day ago
  •  ...Life Insurance Sales Agent Kemper is one of the nation's leading specialized insurers. Our success...  ..., can be highly motivating and productive. Kemper's products and services are making...  ...needed to study for and pass the licensing exams. Once licensed, you will be assigned... 
    Health Insurance
    Full time
    Temporary work
    Traineeship

    Kemper

    Chicago, IL
    2 days ago
  •  ...Future Opening: Life/Health Insurance Position - State Farm Agent Team Member Full Time • Chicago - IL Position...  ...the community to promote State Farm products including auto, home and life insurance...  ...team environment. Life and Health license (must have currently). This... 
    Health Insurance
    Full time
    For contractors
    Work at office

    John Kim - State Farm Agent

    Chicago, IL
    1 day ago
  •  ...a customer-oriented professional, you will market Life/Health insurance services and products to help benefit customers and their families. Your sales...  ...federal regulations. QUALIFICATIONS: State insurance license for life and health insurance. Communication and interpersonal... 
    Health Insurance
    Flexible hours

    Vivian Valtas - State Farm Agent

    Chicago, IL
    5 days ago
  • $50k - $100k

     ...Insurance Agent OpportunityKimbrell Agency is looking for an insurance agent to join their...  ...:Present and sell insurance products to new and existing customers.Reach...  ...Details:This role does require a Life and Health Insurance License, but don't worry—we'll help you obtain... 
    Health Insurance
    Full time
    Part time
    For contractors
    Remote work

    Kimbrell Agency

    Chicago, IL
    1 day ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Licensed Health Insurance Agent (Ancillary Products). Be the first to apply!