Location: Fully Remote – Must be a US Resident
Employment Type: Full-Time
The Weatherspoon Agency (TWA) is expanding in Florida and is actively hiring Remote Benefits Enrollment Agents to primarily serving union members and their families.
For over 70 years, our organization has specialized in providing supplemental life and insurance protection benefits to working-class families through labor unions and associations nationwide. We operate in a 100% union-based environment, serving tens of thousands of organized workers and millions of policyholders across the country. Including the large organizations of the AFL-CIO, UAW, IBT, Teamsters, IBEW, and AFSCME.
Our clients include union members and families in industries such as:
Manufacturing & Skilled Trades
Utility & Energy Workers
Government & Municipal Employees
First Responders & Public Service Professionals
Transportation, Logistics, and Industrial Workers
Our benefits and policy options are reviewed and often selected in collaboration with union and association boards or advisory groups. These benefits are made available to members through their individual union or association membership.
✅ No Cold Calling
We work exclusively with members who respond directly and request outreach, ensuring all conversations are member-initiated and permission-based.
✅ Warm Leads Provided – At No Cost (and they are good leads....)
All leads are supplied by the agency. No prospecting. No out of pocket expenses.
✅ Strong Earning Potential
Competitive income, commissions, performance bonuses, and long-term residual income.
✅ Clear Career Advancement
Structured paths into leadership and management with mentorship and support.
✅ Training & Licensing Support
No prior life insurance experience required. We provide training and assist with Florida and Georgia's life insurance licensing.
✅ 100% Remote
Work from home while serving Florida and Georgia union families statewide.
Meet virtually with union members who have requested benefits information
Explain available life insurance and supplemental benefit options
Help families understand and enroll in coverage that fits their needs
Build long-term, trust-based relationships with policyholders
Maintain Florida resident and Georgia non-resident licensing and compliance requirements
✔ US Resident (required)
✔ Strong communication skills and professionalism
✔ Self-motivated and organized in a remote environment
✔ Coachable and open to structured training
✔ Life insurance license required — we assist with the process
No prior insurance background needed.
Experience in customer service, sales, trades, military, public service, or union environments is always a plus.
The Weatherspoon Agency is a captive agency specializing in union-based supplemental benefits.
Our mission is simple: protect working-class families and provide meaningful career opportunities for our agents.
Recognized nationally for culture and growth
Long-term renewals and residual income model
Leadership development and professional advancement
Stable, recession-resistant industry serving essential workers
Submit your resume today.
Qualified applicants will receive a follow-up email and text with links to:
1⃣ A brief career overview video (role, compensation, expectations)
2⃣ A virtual interview scheduling link
Take the first step toward a stable, purpose-driven remote career serving Florida and Georgia's union families.
The Weatherspoon Agency is an Equal Opportunity Employer. We value diversity and are committed to an inclusive workplace.
Life Insurance Benefits Advisor – Remote (Florida) • Tallahassee, Florida, United States
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