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Shipley Legacy Group

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

Role: Whole Life Insurance Sales Agent

Troy, MT Contract (1099) Posted Sep 1, 2026
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If you're in Troy, MT and ready for work that actually matters — on your own schedule, from home — Shipley Legacy Group is hiring remote whole life insurance agents for career changers from healthcare and skilled trades. This is 100% remote, commission-based 1099 life insurance sales work, meaning you'll serve clients across our service area while working from home in Troy or anywhere with internet.

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.

Apply directly to Shipley Legacy Group

Interested in this role?

Send your information to the hiring team. This opening is accepting applications through September 22, 2026.

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