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Enrollment First, Inc.
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Author: James Kesterson

  • James Kesterson
  • October 2, 2025October 2, 2025

What’s Next in Health Coverage?

What’s Next in Health Coverage for Gig Workers and Contractors?  At Enrollment First, we’re helping professionals across industries access the kind of benefits once reserved only for traditional employees. As the healthcare environment shifts, here’s how we see the landscape evolving —

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Why Brokers Are Turning to eConnect to Grow Faster and Work Smarter
  • James Kesterson
  • September 11, 2025September 12, 2025

Why Brokers Are Turning to eConnect to Grow Faster and Work Smarter

Why Brokers Are Turning to eConnect to Grow Faster and Work Smarter  In today’s rapidly changing benefits landscape, particularly for 1099 contractors, gig workers, and small businesses, brokers require more than just a portfolio of products. Brokers need a smarter, more

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  • James Kesterson
  • September 5, 2025September 5, 2025

Voluntary Benefits that Sell Themselves

Voluntary Benefits that Sell Themselves: What Gig Workers and 1099’s Are Asking For in 2025  As the employment landscape evolves, brokers catering to the 1099 workforce need to recognize a crucial shift: gig workers are actively seeking benefits, and they have

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ACA Compliance Isn’t Optional
  • James Kesterson
  • August 25, 2025August 25, 2025

ACA Compliance Isn’t Optional

What Brokers Need to Know Before It Costs Their Clients Thousands  In today’s evolving benefits environment, brokers face mounting pressure to ensure their clients remain compliant with the Affordable Care Act (ACA). With workforce reforms gaining momentum and regulatory audits becoming

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The Future of Enrollment Isn’t Face-to-Face
  • James Kesterson
  • August 21, 2025August 22, 2025

The Future of Enrollment Isn’t Face-to-Face

The Future of Enrollment Isn’t Face-to-Face: Remote Workforces Changed the Game Remember when benefit enrollment meant clipboards, break rooms, and stacks of paperwork? That era is long gone. Today’s remote, mobile, and hard-to-reach workforce has made traditional enrollment methods not just

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Why Brokers Choose Enrollment First
  • James Kesterson
  • August 5, 2025August 5, 2025

Why Brokers Choose Enrollment First

Health Benefits Platform for Brokers Simplifying Enrollment, Boosting Retention Brokers in today’s fast-paced health benefits environment are under more pressure than ever. Clients expect more than just product recommendations—they want seamless enrollment, year-round support, and simplified compliance. That’s why so many

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