Now recruiting field agents

Build a legacy career in the field.

Legacy365 Insurance is a nationwide Medicare field marketing organization built by agents, for agents. If you love the work, we'll give you the leads, the training, and the back office to grow a book worth passing down.

$100K+
avg. first-year potential
48 hrs
from apply to interview
1:1
mentorship from day one
50
states we serve
Legacy365 Insurance field agent meeting with a senior couple at their home

What you get

Everything you need to grow a real book of business.

Top-tier commissions

Street-level and above with production-based renewals that compound. No caps, no clawback games.

Real, exclusive leads

We invest in lead generation so you invest your time in kitchen-table conversations, not cold outreach.

Contracted with the majors

Top-rated Medicare Advantage, Med Supp, PDP, and ancillary carriers — with the freedom to write what's right for your client.

Training that respects your time

Weekly product deep-dives, sales roleplay, and CMS-compliant certification support.

Legacy365 Insurance agents meeting with Medicare clients and presenting Medicare options.

Our people

A team that picks up the phone.

We're field agents ourselves. That means when you have a carrier question at 4:47pm on an enrollment day, someone who has been in the seat is going to answer.

  • Territories available in all 50 states
  • New-agent bootcamp + experienced-agent fast track
  • Full compliance and CMS certification support
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Leadership

Meet the Founders

Three operators who have spent their careers building agents, agencies, and the systems that let insurance professionals thrive.

David Hill — Founding Managing Member

David Hill

Founding Managing Member

With nearly a decade of experience in Medicare, Dave Hill brings a strong background in sales, recruiting, agent development, and building high-performing teams. Throughout his career, Dave has often been brought in to help build sales centers from the ground…
Email David
Jahsiem Sweat — Founding Managing Member

Jahsiem Sweat

Founding Managing Member

Jahsiem Sweat is a Founding Managing Member of Legacy365 Insurance and the owner of Insurance Training HQ. A recognized leader in Medicare education and agent development, Jahsiem has trained and mentored more than 5,000 Medicare insurance agents across the…
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Nathan Ferdig — Founding Managing Member

Nathan Ferdig

Founding Managing Member

With years of experience in the Medicare insurance industry, Nathan has built a reputation for developing high-performing agents, growing successful agencies, and creating systems that help insurance professionals thrive. Throughout his career, Nathan has…
Email Nathan

For Medicare beneficiaries

Meet our agents

Find a licensed agent in your state, see what they specialize in, and book a meeting on their calendar — no cost, no obligation.

Your best year in the field starts with a conversation.

Apply now and a recruiter will reach out within two business days to set up an interview or informal meet & greet.