Shipley Legacy Group
Annuity Sales Agent
Licensed Agent — Remote Life Insurance & Annuity Sales (1099)
Hiring across 21 markets in 19 states
Albany, OR · Bay St. Louis, MS · Bel Air, MD · Biddeford, ME · Buffalo, WY · Canyon, TX · Cut Bank, MT · Dell Rapids, SD · Doylestown, PA · Fort Lauderdale, FL · Henderson, KY · Lihue, HI · Longmont, CO · Norwich, CT · Pahoa, HI · Revere, MA · Round Rock, TX · Searcy, AR · Secaucus, NJ · Stockbridge, VT · Villa Rica, GA
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 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 looking for licensed agents who want to help families approaching retirement protect what they've built. This is 100% remote, commission-based 1099 work — no salary, no office required.
What you'll actually do
- Reach out to prospective clients and schedule coverage conversations
- Listen to where a client stands financially and what they're trying to protect
- Explain life insurance and annuity options that fit their situation honestly
- Help clients complete applications and follow their cases through underwriting
- Manage your own pipeline and follow up consistently without someone chasing you
- Tap into available call reviews and scripts to sharpen how you present solutions
Who this is a fit for
- Holds an active life insurance license — or is ready to obtain one before selling
- Has experience talking with clients about coverage, financial products, or retirement
- Comfortable working independently and setting your own daily structure
- Wants to focus on retirement and legacy planning, not just term conversions
- Self-directed enough to follow through without a manager checking in daily
What we provide
- Direct carrier appointments available through Shipley Legacy Group
- 1:1 mentorship available from Anissa and Joe Shipley, who built this agency over six years after losing close family members and understanding firsthand why this work matters
- Underwriting advocacy available when a case needs extra support getting through
- Free ongoing training and a weekly team call available to all 17 agents on the team
The honest part
This is commission-only 1099 work — no base pay, no guaranteed income, no benefits package. If you need a steady paycheck while you build a book, this isn't the right fit right now. If you're licensed, serious about the retirement planning space, and ready to work independently, reach out to Shipley Legacy Group and introduce yourself.
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. Annuity Sales Agent at Shipley Legacy Group is 100% remote within the United States. The agency is actively recruiting in 21 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.