Jesse Smedley

Jesse Smedley is a Principal of Oakbridge Insurance and the founder of iHealthBrokers. He founded iHealthBrokers in 2007, and Oakbridge acquired iHealthBrokers in 2025. Today he leads the iHealthBrokers team inside Oakbridge, focused on health insurance and Medicare.

For nearly two decades, Jesse has helped people save money on their health insurance by giving them the resources to educate themselves on all of their options, both under age 65 and as Medicare beneficiaries. His specialty is the Medicare transition: helping people leave employer coverage, avoid late-enrollment penalties, and choose the right plan the first time.

Author of Medicare A to Z: Your Roadmap to Medicare

Jesse wrote Medicare A to Z, a plain-English guide now in its 2026 edition. It walks through how Medicare works part by part, when and how to enroll, the deadlines that can trigger penalties, when you can safely delay Medicare, how to choose between Medicare Advantage, Medigap, and Part D, and how to work with a broker. The e-book is free, and the paperback is available on Amazon.

Educator first

Jesse teaches through the iHealthBrokers YouTube channel, blog, and guides. He is featured in many publications and writes regularly for expert columns on health insurance and Medicare.

The iHealthBrokers approach

iHealthBrokers works with 200+ carriers in all 50 states, is certified on HealthCare.gov and most state marketplaces, serves Spanish-speaking clients, and offers free support for the life of your plan. Clients rate the team 4.9+ across 2,700+ reviews.