Agent - Sean Willingham

Sean Willingham is The Medicare Man. Specializing in Medicare since 2003, Sean has personally helped thousands of Medicare beneficiaries to pick a Medicare plan. As the Medicare chair of the San Antonio Association of Health Underwriters, Sean has provided training to hundreds of insurance agents to be more proficient in Medicare.

“Highway 65” is a trademark owned by Medicare Man LLC, which was co-founded by Sean and his wife Kira. Together they run the agency, take care of customers, and train insurance agents to succeed in the Medicare market. Sean and Kira have 3 children, Jake, Maddie and Reese. In their off time, Sean and Kira can be found at the ballpark watching their children play baseball and softball.


Office Address

1100 NE Loop 410

Suite 300

San Antonio, TX 78209

Office Number


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1100 NE Interstate 410 Loop suite 300, San Antonio, TX 78209, USA

Highway 65 Insurance Copyright 2023 -- All Rights Reserved --

Phone: 210-491-0036


"Highway 65: The Road to Medicare" is a registered trademark of Medicare Man LLC.

We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact or 1-800 MEDICARE to get information on all of your options.