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Shipley Legacy Group

Burned Out on Shift Work? Remote Life Insurance Agent — Healthcare & Trades (1099)

Wauchula, FL Full-time Posted Aug 12, 2026
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In Wauchula, FL, where agricultural families and rural communities value self-reliance and independence, Shipley Legacy Group — a 6-year-old agency founded by Anissa and Joe Shipley — is looking for healthcare workers and tradespeople ready to build their own schedule. This is a remote, work-from-home position serving the Wauchula, FL area, and it is 100% commission-based 1099 work.

What you'll actually do

  • Contact prospective clients to discuss their life insurance needs and options
  • Schedule and hold coverage conversations by phone or video, on your own calendar
  • Listen to each client's situation and explain available policy choices in plain language
  • Help clients complete applications and follow them through the underwriting process
  • Use available scripts and call review resources to keep improving your conversations
  • Set your own hours — no shifts assigned, no punching in or out

Who this is a fit for

  • Healthcare workers or tradespeople ready to trade a rigid schedule for more control
  • People who are comfortable talking with strangers and listening without rushing
  • Self-starters who can work independently without someone checking in constantly
  • Career-changers who want real structure and support while learning something new
  • Anyone willing to obtain a state life insurance license before selling — or already licensed

What we provide

  • Direct carrier appointments available to agents joining the team
  • A 1:1 mentor available to help you find your footing early on
  • Scripts, call reviews, and a weekly team call available to agents who want them
  • Underwriting advocacy available when a client's case needs extra attention

The honest part

This is commission-only 1099 independent-contractor work — no salary, no guaranteed pay, no set hours. If you need a steady paycheck from day one, this isn't the right fit right now. If you're willing to learn and do the work, reach out to Shipley Legacy Group to start a real conversation about whether this makes sense for you.

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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