Remote Benefits Enrollment Agent

Remote Benefits Enrollment Agent

Location: Fully Remote – Must be a US Resident
Employment Type: Full-Time

Looking for a Remote Career With Stability, Purpose, and Growth?

The Weatherspoon Agency (TWA) is expanding in Michigan 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.

Why Join The Weatherspoon Agency?

✅ 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 marketing expenses.

✅ Strong Earning Potential
Competitive 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 insurance experience required. We provide training and assist with Michigan life insurance licensing.

✅ 100% Remote
Work from home while serving Michigan union families statewide.

Key Responsibilities

• 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 Michigan licensing and compliance requirements

What We’re Looking For

✔ 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.

About The Weatherspoon Agency

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

How to Apply

Submit your resume today.
Qualified applicants will receive a follow-up email and text with links to:

1️⃣ A brief career overview video (role, compensation, expectations)
2️⃣ A virtual interview scheduling link

Take the first step toward a stable, purpose-driven remote career serving Michigan’s union families.

The Weatherspoon Agency is an Equal Opportunity Employer. We value diversity and are committed to an inclusive workplace.