Shipley Legacy Group
Whole Life Insurance Sales Agent
Remote Whole Life Insurance Agent — Career Changers From Healthcare & Skilled Trades (1099)
Hiring across 21 markets in 18 states
Auburn, AL · Auburn, ME · Borger, TX · Clarkston, WA · Colorado Springs, CO · Cranford, NJ · Danbury, CT · Dunkirk, MD · Middleton, ID · Middletown, RI · Nichols Hills, OK · Ozark, AR · Paris, TN · Port Angeles, WA · Rochester, MN · Seattle, WA · Sedona, AZ · Springfield, MA · Troy, MI · Weston, VT · Wolcott, VT
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 21 markets across 18 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
You've worked beside people when life goes sideways — on a floor, in the field, or on a job site. Shipley Legacy Group was started by Anissa and Joe Shipley after both lost close family members, and this agency exists because of it. This is 100% remote, commission-based 1099 life insurance sales for career changers who want that to mean something.
What you'll actually do
- Contact prospective clients and schedule coverage conversations from home, on your schedule
- Listen to what a family needs and explain whole life insurance options in plain terms
- Help clients complete applications and follow each case through underwriting
- Use available scripts and call reviews to sharpen how you talk about coverage
- Tap into a 1:1 mentor available through Shipley Legacy Group as you find your footing
- Manage your own pipeline and follow up consistently — no one does that part for you
Who this is a fit for
- Healthcare workers or tradespeople ready to stop letting the shift schedule run their lives
- People who've watched a family scramble after a loss and want to help others avoid that
- Career changers willing to obtain a state life insurance license before selling
- Self-directed adults who can work without supervision or a time clock
- Anyone already comfortable talking to people about serious, real-life topics
- Those who understand flexibility and commission-only pay go hand in hand
What we provide
- Direct carrier appointments available upon joining the team
- 1:1 mentorship and access to weekly team calls available through Shipley Legacy Group
- Scripts, call reviews, and ongoing training available as you build your practice
- Underwriting advocacy to help your clients' cases move forward
The honest part
This is commission-only 1099 work — no salary, no guaranteed income. Shipley Legacy Group has 17 agents and six years in business, but this role isn't for everyone: if you need a steady paycheck while you get started, that's worth knowing now. If the work sounds right, apply below and let's talk.
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. Whole Life Insurance Sales Agent at Shipley Legacy Group is 100% remote within the United States. The agency is actively recruiting in 21 markets across 18 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.