About this episode

Tyler Rees and Josh Benson discuss their journey in the insurance industry and the creation of EnrollHere, an innovative insurance technology platform.

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…

People in this episode

Hosts: Dan Hardle, Mike Hardle

Guests: Tyler Rees, Josh Benson

Topics covered

• Medicare
• insurance technology
• lead generation
• business growth
• entrepreneurship

Keywords

• Medicare FMOs
• final expense insurance
• insurance technology
• lead generation
• cost per acquisition

Mentioned in this episode

Organizations: Humana, Innovative Financial Group, EnrollHere

More episodes of Agent Boost Marketing Podcast

• Episode 128: From Call Center Agent to Agency Owner with Riley Garner · July 10, 2026 · 41 min
• Episode 127: Telesales Agents Are Dead · June 29, 2026 · 59 min
• Episode 126: Alchemy Health Plans with Seth Cottle · June 19, 2026 · 38 min
• Episode 125: ACA Trends and Future with Jeff Gaston · June 15, 2026 · 56 min

Explore listener stats, chart rankings, contacts and more on the Agent Boost Marketing Podcast podcast page.