Work from Home This Fall as a Benefits Enrollment Representative – Seasonal Customer Care Roles with Working Solutions

Working Solutions Benefits Enrollment Representatives

a Sponsored Post by Chris Durst   Oct. 29, 2025

This post is sponsored by Working Solutions. As always, we’ve reviewed the opportunity to ensure it’s legitimate and suitable for our readers. We only share real jobs from reputable companies.

If you’re looking for flexible, work-from-home opportunities this fall — especially if you enjoy helping people — this seasonal Customer Care role with Working Solutions could be a great fit.

You’ll assist federal employees, retirees, and military personnel with their benefits enrollment questions during open enrollment season.

It’s meaningful work that helps people make important decisions about their healthcare and coverage — and it’s a great way to earn from home with a company that’s been connecting independent contractors to top brands for nearly 30 years.

Pssst! This could be a great way to earn before the holidays!


🏡 What You’ll Do

As an independent Benefits Enrollment Representative, you’ll help callers with:

  • Creating new accounts

  • Answering plan and enrollment questions

  • Navigating online benefit tools

You’ll be part of a team that supports retired military, veteran, and federal personnel — people who truly appreciate friendly, patient help.

This is a seasonal opportunity, with the busiest period running November 10 – December 8, 2025. If things go well, you may be able to roll right into another program afterward — many agents continue working with Working Solutions year-round (hint hint their big TurboTax program is coming up).


🌟 Why Agents Love Working Solutions

  • Work from home – Skip the commute and work comfortably from your own space.

  • Create your own schedule – Choose hours that fit your life. Program hours run 7am–8pm CT, Monday–Friday, and may expand during open enrollment.

  • Supportive environment – Agents rated Working Solutions an outstanding 91 on the Net Promoter Score (NPS) last year, reflecting high satisfaction.

  • Diverse opportunities – Once this project wraps up, you can explore other programs in healthcare, retail, pet tech, travel, and more.


💰 Pay & Incentives

This is an independent contractor role. Pay is based on Customer Interaction Minutes (CIM):

  • $0.28 per minute for English interactions

  • $0.31 per minute for Spanish interactions

You’ll be provided a minimum of 54 minutes per productive hour, and the program also includes incentive opportunities for top performers.


🧰 What You’ll Need

No specialized experience is required — just great customer service skills and a friendly, professional demeanor.

You’ll also need:

  • A quiet, uninterrupted workspace

  • A Windows 11 PC (or Intel-based Mac with Windows 11 via Boot Camp)

  • Wired high-speed internet (no Wi-Fi, satellite, or mobile internet)

  • A wired USB headset with microphone

  • A smartphone to receive work-related texts


🌎 Who Can Apply

Working Solutions contracts with agents across the U.S., but for this specific program, they cannot currently work with residents of:  CA, CO, CT, DC, DE, IL, MA, MD, MN, MT, NH, NJ, NY, OR, PA, VT, WA, or WI.

If you live in one of these states, you can still find other opportunities at apply.workingsolutions.com


✅ Ready to Apply?

If you’re looking for flexible, legitimate remote work with a supportive team and real impact, don’t wait — the open enrollment season starts soon!

👉 Click here to apply for the Benefits Enrollment Representative – Customer Care program.



(Friendly reminder, Rat Race Rebellion doesn’t play a role in the applications or hiring processes for jobs we’ve posted to our site. We’re a job board and blog.)

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