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Shipley Legacy Group

Remote Whole Life Insurance Agent — Career Changers From Healthcare & Skilled Trades (1099)

Galesburg, IL Full-time Posted Aug 12, 2026
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Galesburg, IL is home to hardworking professionals and administrators who understand the value of protecting what matters most. If you've worked in healthcare or skilled trades and are ready to build something meaningful on your own terms, Shipley Legacy Group is hiring remote whole life insurance agents. This is a 100% remote, work-from-home position serving the Galesburg, IL area — you'll work from wherever you choose, on a schedule that fits your life.

What you'll actually do

  • Contact prospective clients and schedule coverage conversations from home, on your schedule
  • Listen to what a family needs and explain whole life insurance options in plain terms
  • Help clients complete applications and follow each case through underwriting
  • Use available scripts and call reviews to sharpen how you talk about coverage
  • Tap into a 1:1 mentor available through Shipley Legacy Group as you find your footing
  • Manage your own pipeline and follow up consistently — no one does that part for you

Who this is a fit for

  • Healthcare workers or tradespeople ready to stop letting the shift schedule run their lives
  • People who've watched a family scramble after a loss and want to help others avoid that
  • Career changers willing to obtain a state life insurance license before selling
  • Self-directed adults who can work without supervision or a time clock
  • Anyone already comfortable talking to people about serious, real-life topics
  • Those who understand flexibility and commission-only pay go hand in hand

What we provide

  • Direct carrier appointments available upon joining the team
  • 1:1 mentorship and access to weekly team calls available through Shipley Legacy Group
  • Scripts, call reviews, and ongoing training available as you build your practice
  • Underwriting advocacy to help your clients' cases move forward

The honest part

This is commission-only 1099 work — no salary, no guaranteed income. Shipley Legacy Group has 17 agents and six years in business, but this role isn't for everyone: if you need a steady paycheck while you get started, that's worth knowing now. If the work sounds right, apply below and let's talk.

Ready to serve Galesburg and beyond with whole life insurance that makes a real difference? Apply now and connect with the Shipley Legacy Group team.

Apply directly to Shipley Legacy Group

Interested in this role?

Send your information to the hiring team. This opening is accepting applications through August 31, 2026.

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