Shipley Legacy Group
Life Insurance Sales Agent
Former Teachers & School Staff — Remote Life Insurance Agent (1099)
Hiring across 23 markets in 20 states
Bothell, WA · Bryan, TX · Chambersburg, PA · Crosby, ND · Davenport, IA · Enid, OK · Farmington, CT · Florence, CO · George, WA · Greencastle, IN · Imlay City, MI · Kadoka, SD · Kaunakakai, HI · Lebanon, ME · Metairie, LA · Mina, NV · North Las Vegas, NV · Ocean City, MD · Owyhee, NV · Paducah, KY · Perth Amboy, NJ · Summersville, WV · Warwick, RI
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 20 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
Former teachers and school staff already know how to build trust and explain complex topics clearly. Shipley Legacy Group is looking for people ready to put those skills to work in a 100% remote, commission-based 1099 life insurance sales role.
What you'll actually do
- Contact prospective clients who've already asked about life insurance coverage
- Schedule and hold conversations to understand what protection a client needs
- Explain term life, whole life, or final expense options in plain, honest language
- Help clients complete applications and follow each one through underwriting
- Use scripts and call review resources available through Shipley Legacy Group to sharpen your approach
- Manage your own pipeline and follow through consistently with each client
Who this is a fit for
- Current or former teachers, counselors, coaches, paraprofessionals, or school administrators
- People who hold a state life insurance license — or are willing to obtain one before their first sale
- Comfortable leading one-on-one conversations over the phone
- Self-directed enough to work without anyone managing your daily schedule
- Looking for 100% remote work with hours you control
- Drawn to a team with a real reason for being — Anissa and Joe Shipley built this agency after losing close family members and seeing firsthand what a life insurance policy means to the people left behind
What we provide
- Direct carrier appointments available to agents on the team
- A 1:1 mentor available to work with you as you get started
- Scripts, call reviews, and weekly team calls you can join
- Underwriting advocacy available when your clients need support navigating the process
The honest part
This is commission-only, 1099 independent-contractor work — no salary, no guaranteed pay. If a steady paycheck is what you need right now, this isn't the right fit. If you want to learn more about joining Shipley Legacy Group's 17-agent team, apply below and someone will reach out to walk you through the next step.
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 23 markets across 20 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.