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Shipley Legacy Group

Nurses, CNAs & Skilled Trades — Remote Life Insurance Agent (1099)

Okeechobee, FL Full-time Posted Aug 12, 2026
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Shipley Legacy Group is hiring nurses, CNAs, home health aides, and skilled tradespeople in the Okeechobee, FL area who are ready to bring their instinct for explaining hard things in difficult moments to 100% remote, commission-based 1099 life insurance work. This is a remote, work-from-home position serving Okeechobee and surrounding communities — you'll work entirely from home on your own schedule.

What you'll actually do

  • Contact prospective clients who've asked about life insurance coverage
  • Schedule and hold coverage conversations by phone or video call
  • Listen to each client's situation and explain available policy options clearly
  • Help clients complete applications and track their cases through underwriting
  • Work independently, setting your own hours around your current commitments
  • Use call review resources and scripts available through the agency when you need them

Who this is a fit for

  • Healthcare workers and tradespeople ready for a meaningful career shift
  • People already comfortable having honest conversations about serious topics
  • Self-directed individuals who don't need someone managing their daily schedule
  • Those who hold a state life insurance license — or are willing to obtain one before selling
  • Anyone with a computer, a phone, and reliable internet at home

What we provide

  • Direct carrier appointments available through Shipley Legacy Group
  • 1:1 mentorship available from day one alongside scripts and call reviews
  • Weekly team call available to connect with the agency's 17 active agents
  • Underwriting advocacy available when a client's case needs extra attention

The honest part

This is commission-only 1099 work — no hourly wage, no salary. Anissa and Joe Shipley started Shipley Legacy Group after losing close family members and learning firsthand what a missing policy costs a grieving family; if that mission resonates with the work you've already been doing, it's worth a conversation. If you need guaranteed pay right now, this isn't the right fit — if you don't, reach out and let's talk.

Okeechobee families and ranching operations deserve straightforward answers about life insurance from someone who listens. If you're ready to do that work from home on your own terms, we want to hear from you. Apply now or call Shipley Legacy Group to learn more.

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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