Shipley Legacy Group
Life Insurance Sales Agent
Burned Out on Shift Work? Remote Life Insurance Agent — Healthcare & Trades (1099)
Hiring across 28 markets in 24 states
Aurora, IL · Bairoil, WY · Bay City, MI · Bay Minette, AL · Beckley, WV · Blue Hill, ME · Bonney Lake, WA · Boothbay Harbor, ME · Columbia, SC · Derby Line, VT · Elko, NV · Faith, SD · Florence, OR · Holcomb, KS · Jackson, GA · Lodi, NJ · Madison, WI · Manville, WY · Monson, MA · Oxford, NC · Poplar Bluff, MO · Sunnyside, WA · Syracuse, NE · Troy, MT · Valdez, AK · Waldorf, MD · Waubay, SD · Xenia, OH
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 28 markets across 24 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
If you're a nurse, CNA, EMT, or trades worker who's done letting a shift schedule run your life, Shipley Legacy Group — a 6-year-old agency founded by Anissa and Joe Shipley — is worth a serious look. This is 100% remote, commission-based 1099 work.
What you'll actually do
- Contact prospective clients to discuss their life insurance needs and options
- Schedule and hold coverage conversations by phone or video, on your own calendar
- Listen to each client's situation and explain available policy choices in plain language
- Help clients complete applications and follow them through the underwriting process
- Use available scripts and call review resources to keep improving your conversations
- Set your own hours — no shifts assigned, no punching in or out
Who this is a fit for
- Healthcare workers or tradespeople ready to trade a rigid schedule for more control
- People who are comfortable talking with strangers and listening without rushing
- Self-starters who can work independently without someone checking in constantly
- Career-changers who want real structure and support while learning something new
- Anyone willing to obtain a state life insurance license before selling — or already licensed
What we provide
- Direct carrier appointments available to agents joining the team
- A 1:1 mentor available to help you find your footing early on
- Scripts, call reviews, and a weekly team call available to agents who want them
- Underwriting advocacy available when a client's case needs extra attention
The honest part
This is commission-only 1099 independent-contractor work — no salary, no guaranteed pay, no set hours. If you need a steady paycheck from day one, this isn't the right fit right now. If you're willing to learn and do the work, reach out to Shipley Legacy Group to start a real conversation about whether this makes sense for you.
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. Life Insurance Sales Agent at Shipley Legacy Group is 100% remote within the United States. The agency is actively recruiting in 28 markets across 24 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.