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Health Insurance Agent

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60290, USA
Listing for: Pitch Health Solutions
Remote/Work from Home position
Listed on 2026-02-07
Job specializations:
  • Sales
    Insurance Sales
Salary/Wage Range or Industry Benchmark: 2000 - 3000 USD Weekly USD 2000.00 3000.00 WEEK
Job Description & How to Apply Below

Pitch Health Solutions is a rapidly growing national agency specializing in Medicare Advantage, Final Expense, and more, giving you unlimited opportunities to grow, maximize commissions, and build a long-term career in the industry.

This job is fully remote.

Your Path With Us Step 1:
Start of Employment (Transfer Agent Role)

Start your journey with a paid 2 to 4 week onboarding program where you will:

  • Use our dialer to outbound connect pre-qualified seniors with licensed agents and gain real‑time call experience and confidence
  • Complete carrier contracting & certifications
  • Receive hands‑on coaching from industry experts

Once your contracting is complete, you’ll seamlessly transition to the next phase.

Step 2:
Medicare & Senior Benefits Specialist

After onboarding, you will step into a fully active sales role with:

  • 100% inbound calls – no cold calling, no hunting, no chasing
  • A steady flow of interested, qualified prospects from our in‑house marketing team
  • Live client transfers from individuals ready to explore Medicare or Final Expense coverage
  • The bandwidth to focus solely on what matters: connecting, educating, and closing
Compensation & Perks Start of Employment (Transfer Agent Role)
  • Paid 2 to 4 week onboarding with live call training and real call experience
  • Full‑time schedule:
    Monday to Friday, from 9 AM to 6 PM EST (occasional Saturdays)
  • Includes a 1‑hour lunch break
  • 100% Remote – Work from anywhere nationwide
  • Hands‑on coaching, skill‑building, and a clear path to promotion into your Medicare Specialist role
Medicare & Senior Benefits Specialist
  • $18–$20/hour base pay (based on experience)
  • Lucrative, performance‑driven commissions
  • Top‑performing Specialists consistently earn $2,000–$3,000 per week
  • All inbound calls – no cold calling, ever
  • Full‑time schedule:
    Monday to Friday, from 9 AM to 6 PM EST (occasional Saturdays)
  • Includes a 1‑hour lunch break
  • 100% Remote – Earn nationwide from the comfort of your home
  • Endless growth opportunities in a rapidly expanding organization
What You’ll Do as an Active Sales Agent
  • Sell Medicare and Final Expense plans
  • Educate seniors, guide them through their options, and enroll them in coverage
  • Meet sales goals while maintaining compliance and professionalism
What We’re Looking For
  • Active health insurance license – licensed in 7+ states is a plus
  • 1+ year of insurance sales experience preferred (not required)
  • Strong closer with excellent communication skills
  • Coachable, motivated, and results‑driven
  • Tech‑ready: PC/laptop (i5+, 8GB RAM), wired internet, USB headset
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