EnrollHere founders Tyler Rees and Josh Benson trace their paths through insurance sales and technology. The conversation moves from building distribution and generating business to the challenges of Medicare Advantage marketing. They discuss distinguishing marketing publishers from other distribution participants, improving vetting and audits, and using technology to monitor, measure, and score telephonic enrollments and reduce churn.

In this episode

  • Insurance entrepreneurship
  • Enrollment technology
  • Marketing publisher oversight
  • Telephonic quality monitoring
  • Medicare retention

Show notes

On Episode 129 of the Agent Boost Podcast, Dan and Mike sit down with Tyler Rees and Josh Benson, longtime friends and business partners who built one of the fastest growing Medicare FMOs in the country before selling it to Humana.

Tyler and Josh trace their path back to central Pennsylvania, where they started out selling final expense insurance door to door, eventually founding Innovative Financial Group (IFG), scaling it to over $125 million in final expense premium and $300 million in annuities, then pivoting hard into Medicare in 2020. That pivot took them from 4,500 apps their first AEP to more than 25,000 the next year, and eventually to an 18 month acquisition process that ended with Humana buying the company in 2022.

The second half of the conversation shifts to what Tyler and Josh are building now: EnrollHere, an insurance technology platform designed to solve the industry's biggest blind spot, siloed data and a total lack of accountability in lead generation and marketing. They break down how EnrollHere's call control and compliance scoring tools have helped partners cut cost per acquisition in half, why they see themselves as a neutral "Switzerland" in the distribution world rather than a competitor, and the audit framework they're building to finally hold publishers and marketers to the same standard agents and agencies already face.

They also get into the mechanics most people never see: how hierarchy actually works when one agent reports to multiple upline agencies, why lifetime value varies so wildly between partners, and why they believe cracking Medicare Advantage is the hardest and most valuable problem in the industry to solve. It's a candid look at building, selling, and rebuilding in a space that rewards the operators willing to actually understand the data.

Chapters

  • 0:00 Welcome & Introducing Tyler Rees and Josh Benson
  • 1:19 Childhood Friends Turned Business Partners in Insurance
  • 4:58 Splitting Paths - Corporate Detour vs. Going Independent
  • 6:03 The Cold-Call Trick That Built a 400-Agent Team
  • 9:17 Founding IFG and Buying Out the Business
  • 11:33 The Pivot to Medicare & a Massive First AEP
  • 14:35 The Call From Humana & an 18-Month Diligence Process
  • 17:31 Scaling Post-Acquisition, the Walmart Deal & Stepping Away
  • 23:56 Why They Built EnrollHere - Solving Insurance's Data Problem
  • 28:51 Staying "Switzerland" & Building the MVP With Niko and Tim
  • 34:06 The Call Center Breakthrough - Cutting CPAs in Half
  • 38:08 Why Data Beats Gut Feel on Lead Quality
  • 40:01 The Marketing Accountability Gap in Medicare
  • 44:02 Spoofed Numbers, Dupe Routing & Bad Actor Tactics
  • 48:01 Building a Compliance Audit Standard for Publishers
  • 53:08 Is Telesales Dead? Why Phone Enrollment Still Matters
  • 54:23 Shared Visibility & the End of "Pay and Pray"
  • 59:43 What the Lifetime Value Data Actually Shows
  • 1:02:12 Beyond Medicare - ACA, Final Expense & Attachment Rates
  • 1:06:22 Cracking Hierarchy - EnrollHere's Core Advantage & Wrap Up