Shipley Legacy Group
Sales Representative
Remote Sales Agent — Evenings & Weekends (1099)
Hiring across 5 markets in 5 states
Hawthorne, NV · Lancaster, OH · Sterling, IL · Weirton, WV · Winchendon, MA
This role is remote — the markets are where we are actively recruiting.
- Pay
- Commission-only, 1099 independent contractor — no base salary, no hourly wage
- License
- Not required to apply — you will need a state license before your first sale
- Where
- Remote anywhere in the US · actively recruiting in 5 markets across 5 states
- Applying takes
- About two minutes — name, email, phone, whether you hold a license, optional résumé
- Who reads it
- A person at Shipley Legacy Group, not an automated screen
Shipley Legacy Group is hiring remote life insurance sales agents who want to work evenings and weekends around their current schedule. 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.
Questions people ask about this role
Is this a salaried job?
No. Shipley Legacy Group contracts independent agents (1099). Pay is commission-only: no base salary, no hourly wage, and no guaranteed income. Individual results depend on individual effort and are not guaranteed.
Do I need a life insurance license to apply?
No. You can apply before you are licensed. You will need a state life insurance license before your first sale, and Shipley Legacy Group walks new agents through getting one during onboarding.
Is the role really remote?
Yes. Sales Representative at Shipley Legacy Group is 100% remote within the United States. The agency is actively recruiting in 5 markets across 5 states, but you can work from anywhere in the US.
What does Shipley Legacy Group provide?
Direct carrier appointments; Set your own schedule; Underwriting advocacy; 1:1 mentor; Scripts + call reviews.
What happens after I apply?
You get an automatic confirmation right away. A person at Shipley Legacy Group reads every application and reaches out directly to set up a first conversation — there is no automated screening.
How long does the application take?
About two minutes: your name, email, phone, whether you currently hold a life insurance license, and an optional résumé.
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.