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Shipley Legacy Group

Remote Sales Agent — Evenings & Weekends (1099)

Role: Sales Representative

Sterling, IL Contract (1099) Posted Sep 28, 2026
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Shipley Legacy Group is hiring remote life insurance sales agents in Sterling, IL who want to work evenings and weekends around their current schedule. This is a remote, work-from-home position. The role suits people ready to learn a clear process, help families find the right coverage, and grow at their own pace — with support available from a 17-agent team.

What you'll do

  • Reach out to individuals who have already asked for information about life insurance
  • Schedule coverage conversations for evenings or weekends by phone or video
  • Listen to each person's situation before walking through any options
  • Explain coverage in plain terms and help clients complete an application together
  • Keep clients informed while their application moves through the carrier's review process
  • Log notes and follow-up tasks in the CRM after each call

Qualifications

  • A state life insurance license, or the ability to pass a licensing exam before your first sale
  • Reliable computer, phone, and internet for remote work
  • Consistent evening or weekend availability you can hold week over week
  • Comfortable holding conversations by phone or video and following through on commitments
  • Able to work independently and manage your own schedule

What we provide

  • Direct carrier appointments through Shipley Legacy Group
  • A 1:1 mentor available as you get started
  • Scripts, call reviews, and ongoing training available at your pace
  • Weekly team calls with an established group of 17 agents

Compensation

This is a 1099 independent contractor opportunity with Shipley Legacy Group. Compensation is commission-based. No salary or hourly pay is provided. Earnings depend on individual production. If you're looking for a remote sales role you can build on evenings and weekends, apply below.

Apply directly to Shipley Legacy Group

Interested in this role?

Send your information to the hiring team. This opening is accepting applications through October 19, 2026.

Do you currently hold a life insurance license?

PDF, DOC, or DOCX · max 4 MB. You can apply without a resume.

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Sales Representative in Sterling, IL · Shipley Legacy Group