Shipley Legacy Group
Sales Representative
Remote Sales Agent — Retail & Hospitality Managers Welcome
Hiring across 23 markets in 19 states
Amargosa Valley, NV · Cambridge, OH · Campbellsville, KY · Columbia, TN · Crawfordsville, IN · Eagle Pass, TX · East Granby, CT · Green Lake, WI · Island Pond, VT · Lovell, WY · Madison, NJ · Manchester Center, VT · Meredith, NH · Milford, DE · Morganton, NC · New Albany, IN · Newberry, SC · Norristown, PA · Plant City, FL · Schererville, IN · Senatobia, MS · Ulysses, KS · Wabash, IN
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 23 markets across 19 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 sales representatives to help individuals and families review and apply for life insurance coverage. This role suits people who've spent years managing customer relationships — retail, restaurant, and hospitality managers who know how to earn trust quickly and are ready to put that skill to work selling something that genuinely matters.
What you'll do
- Reach out to people who've already requested information about life insurance coverage
- Schedule and hold remote appointments by phone or video — no office, no commute
- Ask the right questions to understand a family's situation before presenting any options
- Walk clients through coverage choices clearly and guide completed applications
- Track every conversation and follow-up in the agency CRM as the work happens
- Keep clients informed while their application moves through the carrier review process
Qualifications
- A state life insurance license, or a commitment to obtain one before selling
- Comfortable holding professional conversations by phone and video
- Reliable computer, phone, and internet connection
- Organized follow-through — applications don't close themselves
- Background explaining options to people who didn't ask for a lecture
What we provide
- Direct carrier appointments available to appointed agents
- 1-on-1 mentor access, scripts, call reviews, and weekly team calls available through Shipley Legacy Group's six-year-old, 17-agent operation
- Ongoing product and sales training — not a single onboarding week
- Underwriting advocacy to support cases while they're in review
- A fully remote setup — work from home, anywhere in the U.S., on a schedule you set
Compensation
This is a 1099 independent contractor opportunity. Compensation is commission-based — no salary or hourly pay is provided. Earnings depend on individual production. Qualified candidates who want to build a client book on their own terms are encouraged to apply.
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 23 markets across 19 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.