Shipley Legacy Group
Life Insurance Sales Agent
From Shift Work to Remote Life Insurance Agent — Healthcare & Trades Career Changers (1099)
Hiring across 43 markets in 25 states
Agawam, MA · Austin, NV · Barbourville, KY · Bear, DE · Bergenfield, NJ · Caribou, ME · Chugwater, WY · Del City, OK · Dixon, IL · Everett, WA · Gary, IN · Grand Forks, ND · Grandview, WA · Hallowell, ME · Hartwell, GA · Hebron, NE · Hebron, NH · Heyburn, ID · Hyannis, MA · Jackpot, NV · Jamestown, ND · Lake Charles, LA · Las Cruces, NM · Lawrenceburg, KY · Lincoln, ME · Logan, UT · Merrill, WI · Ninilchik, AK · North Pole, AK · Oconomowoc, WI · Okeechobee, FL · Page, AZ · Price, UT · Quincy, IL · Radcliff, KY · Rice Lake, WI · Salyersville, KY · Sarasota, FL · Silver Springs, NV · St. Charles, MO · Taos, NM · Taylorsville, UT · Toledo, 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 43 markets across 25 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, paramedic, electrician, or machinist who's done letting the shift schedule own you, Shipley Legacy Group is looking for remote, commission-based 1099 life insurance agents. No insurance background required to get started — just a willingness to learn and do the work.
What you'll actually do
- Contact prospective clients by phone to introduce life insurance coverage options
- Schedule and hold one-on-one coverage conversations around your own calendar
- Listen to each client's situation and walk them through policy options that fit their needs
- Help clients complete an application and follow it through underwriting
- Use scripts and call-review resources available through the agency to sharpen your approach
- Lean on a 1:1 mentor when you hit a case or conversation you're not sure how to handle
Who this is a fit for
- Healthcare workers or tradespeople ready to leave rotating shifts and mandatory overtime behind
- People who are good at explaining complicated things clearly — that skill transfers directly here
- Self-starters who can hold themselves accountable without a manager hovering
- Someone willing to obtain a state life insurance license before selling, or who already holds one
- Comfortable working independently from home with a phone, computer, and reliable internet
- Someone who wants a schedule they build, not one handed to them at the start of the week
What we provide
- Direct carrier appointments available to agents from day one
- 1:1 mentorship and scripts available to support your learning curve
- Free ongoing training and a weekly team call available to all agents on the team
- Underwriting advocacy available when a client's case needs extra attention
The honest part
This is 100% commission-based 1099 work — no salary, no guaranteed pay, and no shortcuts. Anissa and Joe Shipley started this agency after losing close family members and learning firsthand why this coverage matters; they've been building the team for six years. If you bring the discipline, Shipley Legacy Group has the structure to help you learn the business. Apply below to start the conversation.
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 43 markets across 25 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.