Remote Benefits Enrollment Agent

Location: Fully Remote – Must Reside in Florida (or Georgia, North Carolina, Ohio, South Carolina, or Tennessee)
Employment Type: Full-Time

Looking for a Remote Career with Growth Potential?

The Weatherspoon Agency (TWA) , has been a leader in supplemental benefits for over 68 years. We are the only 100% union-based insurance provider, proudly serving over 40,000 labor unions nationwide and protecting 5+ million policyholders.

Our clients include working-class professionals such as military personnel, law enforcement, first responders, government employees, auto workers, teamsters, and members of the music, entertainment, and professional sports industries —including the Dallas Cowboys, Texas Rangers, and Atlanta Braves.

Why Join Us?

✅ No Cold Calling – Clients request our services directly through their union and association representatives.
✅ Warm Leads Provided at No Cost – No need to prospect; all leads are provided to you.
✅ Financial Growth – Earn competitive bonuses, commissions, and monthly residual income.
✅ Career Advancement – Pathways into leadership and executive roles , with structured training and mentorship.
✅ Comprehensive Training – No prior experience required; we provide all training and licensing assistance.
✅ Fully Remote – Work from home with flexibility while making a meaningful impact.

Key Responsibilities

• Connect with union and association members who have requested benefits.
• Educate clients on available life, accident, and supplemental health insurance options.
• Build trust-based relationships and provide ongoing support to policyholders.
• Maintain licensing, agency, and compliance requirements.

What We're Looking For

✔ ****Must Reside in Florida (or Georgia, North Carolina, Ohio, South Carolina, or Tennessee)
✔ No prior experience required – We welcome applicants from diverse backgrounds.
✔ Self-Motivated & Organized – Ability to manage time effectively in a remote setting.
✔ Coachable & Adaptable – Willingness to learn and develop new skills.
✔ Licensing Requirement – A life insurance license is required, but we assist with licensing if you are not currently licensed, including a scholarship program for out-of-state applicants (or a temporary Georgia license option for residents of Georgia)

About Us

The Weatherspoon Agency (TWA) is a captive agency. For over 70 years , we have specialized in supplemental benefits for union members, credit unions, and associations , ensuring financial security for working-class families.

• Industry Recognition – Named one of Forbes' " Top 25 Happiest Places to Work."
• **** Growth-Focused Culture – Clear leadership growth paths and professional development opportunities.
• Residual Renewal Income with a 10 year Vestment – Build long-term financial stability with recurring commissions. You're fully vested in just 10 years. That means you'll receive lifetime renewal income—even if you decide to step away—creating true financial security and long-term wealth.

How to Apply

Submit your resume today! If selected, you will receive an email and text with a link to:
1⃣ Watch a career overview video covering role details, compensation, and company culture.
2⃣ Schedule a virtual interview to discuss your fit for the position.

Take the first step toward a rewarding remote career today!

TWA is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive workplace for all employees.