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Shipley Legacy Group

Former Teachers & School Staff — Remote Life Insurance Agent (1099)

Role: Life Insurance Sales Agent

Hanna, WY Contract (1099) Posted Sep 1, 2026
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Hanna, WY—if you're a former teacher or school staff member looking to redirect your skills into independent work on your own terms, Shipley Legacy Group has a 100% remote opportunity waiting. This is a remote, work-from-home position serving the Hanna, WY area and beyond, built for people ready to turn their gift for trust-building into meaningful income.

What you'll actually do

  • Contact prospective clients who've already asked about life insurance coverage
  • Schedule and hold conversations to understand what protection a client needs
  • Explain term life, whole life, or final expense options in plain, honest language
  • Help clients complete applications and follow each one through underwriting
  • Use scripts and call review resources available through Shipley Legacy Group to sharpen your approach
  • Manage your own pipeline and follow through consistently with each client

Who this is a fit for

  • Current or former teachers, counselors, coaches, paraprofessionals, or school administrators
  • People who hold a state life insurance license — or are willing to obtain one before their first sale
  • Comfortable leading one-on-one conversations over the phone
  • Self-directed enough to work without anyone managing your daily schedule
  • Looking for 100% remote work with hours you control
  • Drawn to a team with a real reason for being — Anissa and Joe Shipley built this agency after losing close family members and seeing firsthand what a life insurance policy means to the people left behind

What we provide

  • Direct carrier appointments available to agents on the team
  • A 1:1 mentor available to work with you as you get started
  • Scripts, call reviews, and weekly team calls you can join
  • Underwriting advocacy available when your clients need support navigating the process

The honest part

This is commission-only, 1099 independent-contractor work — no salary, no guaranteed pay. If a steady paycheck is what you need right now, this isn't the right fit. If you want to learn more about joining Shipley Legacy Group's team and building a career that works around your life, apply below and someone will reach out to walk you through the next step.

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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Former Teachers & School Staff — Remote Life Insurance Agent (1099) · Careers at Shipley Legacy Group