Remote Benefits Enrollment Agent Job at The Weatherspoon Agency, United States

Rlo1WTNXdjBqUGwrN3VjUm5rWGI3TGh0Wnc9PQ==
  • The Weatherspoon Agency
  • United States

Job Description

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:

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 Michigan's union families.

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

Job Tags

Full time, Remote work,

Similar Jobs

Utah Staffing

Housekeeping Lobby Attendant Job at Utah Staffing

 ...Housekeeping Lobby Attendant Bring your career to life at Asher Adams! Be part of something extraordinary in Salt Lake City. Asher Adams, located in the iconic Union Pacific Depot, is where historic charm meets modern luxury-and we're building a team to match. Here... 

Glazer's Beer and Beverage, LLC

District Sales Manager Job at Glazer's Beer and Beverage, LLC

 ...Represents Glazers in a professional Manner Ensures the attainment of sales goals for the assigned district through the regular evaluation...  ...cases, and stand for extended periods of time. Glazers Beer and Beverage provides equal employment opportunities to... 

Housing Authority of Kansas City

Legal Assistant Job at Housing Authority of Kansas City

Description: Job Description Job Title: Legal Assistant Department : Legal Department Reports to : General Counsel FLSA Status : Exempt JOB...  ...: The duties of the Legal Assistant primarily involve office work in the legal department. Performs administrative work that is... 

Maryland Staffing

Delivery Truck Driver (Log II) (Government) Job at Maryland Staffing

 ...Delivery Truck Driver AT&T Global Public Sector is a trusted provider of secure, IP enabled, cloud-based, network solutions and professional...  ...to join our team? Apply today! Our Delivery Truck Driver (Log II) (Government) earns between $74,100 - $91,600 yearly. Not to... 

Muse Vineyards

Kitchen Staff/Tasting Room Associate Job at Muse Vineyards

 ...Description Job Description Responsibilities: Prepare all served food Plan food production to coordinate with meal serving hours...  ...well in teams We are also looking for someone to work in the tasting room so you would have the ability to train in that area as well...