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Shipley Legacy Group

Strong Work Ethic, Wrong Industry? Remote Term Life Insurance Agent (1099)

Remote — United States Contract (1099) Posted Aug 18, 2026

Hiring across 10 markets in 10 states

Ashland, OR · Camden, NJ · Corpus Christi, TX · Freeport, IL · Jennings, LA · Monticello, KY · Orofino, ID · Sun Prairie, WI · Tea, SD · Wheatland, WY

This role is remote — the markets are where we are actively recruiting.

Start my application

If you work in healthcare or a skilled trade and you're done letting a rotating shift decide when you sleep, eat, or see your family — Shipley Legacy Group is hiring remote, commission-based 1099 life insurance agents. The work is 100% remote and the schedule is yours to set.

What you'll actually do

  • Contact prospective clients to discuss term life coverage options
  • Schedule and hold one-on-one coverage conversations by phone or video
  • Listen carefully to what a family needs and explain available policy options plainly
  • Help clients complete applications and follow their file through underwriting
  • Use available scripts and call reviews to sharpen how you explain coverage
  • Tap into the weekly team call when it fits your schedule for questions and peer input

Who this is a fit for

  • Nurses, EMTs, CNAs, tradespeople, or anyone already used to talking through hard situations with people
  • Workers burned out on mandatory overtime, rotating shifts, or someone else's clock
  • Self-starters who can manage a day without a supervisor assigning every task
  • People willing to obtain the required state life insurance license before selling
  • Candidates who want straight answers about what the work actually looks like before they commit

What we provide

  • A 1:1 mentor is available — Anissa and Joe Shipley built this agency after losing close family members and they take that seriously
  • Scripts, call reviews, and free ongoing training are available to agents on the team
  • Direct carrier appointments are available once you're licensed
  • A weekly team call is available for support — Shipley Legacy Group has run this for six years with 17 agents currently on the team

The honest part

This is 100% commission-based 1099 work. There is no salary and no guaranteed pay — if that doesn't fit where you are right now, this isn't the right move. If you're ready to find out more, apply and someone from Shipley Legacy Group will follow up with you directly.

Apply directly to Shipley Legacy Group

Interested in this role?

Send your information to the hiring team. This opening is accepting applications through September 20, 2026.

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