Legacy365 Insurance

About us

Built by agents who never stopped working the field.

Legacy365 Insurance was founded on a simple idea: the best field marketing organization is one whose leaders still show up at a kitchen table on a Tuesday. Every policy, every product line, every training we roll out is filtered through one question — does this help our agent do right by their client?

Agent shaking hands with a senior couple after enrolling them in a Medicare plan

Our mission

Help every American aging into Medicare find a plan that actually fits their life — and build a career that lets our agents raise families, retire well, and leave a legacy.

What we believe

  • Client first. The right plan beats the biggest commission — every time.
  • Agent first. Contracts, support, and technology built for the person doing the work.
  • Compliance always. CMS-certified, carrier-approved, and audit-ready.
  • Long game. Renewals compound. Reputations compound. We're building both.

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…
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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…
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Ready to see if Legacy365 is a fit?

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