Welcome to Flanagan Insurance Services
Choosing health insurance or Medicare coverage can feel overwhelming—but it doesn't have to.
I'm Chad Flanagan, founder of Flanagan Insurance Services. I started this agency with one mission: to provide honest guidance, personalized service, and long-term support to individuals, families, retirees, and small businesses throughout Wisconsin and Minnesota.
As an independent broker, I represent multiple insurance companies, allowing me to focus on finding the coverage that best fits your needs—not the needs of one insurance carrier.
Whether you're turning 65, preparing for retirement, looking for Marketplace coverage, or reviewing your current benefits, I'm here to help you make informed decisions with confidence.
Working Together is Simple
① Schedule a Conversation
② Review Your Needs
③ Compare Your Options
④ Choose Coverage
⑤ Ongoing Support
Proudly Veteran-Owned
Military service taught me the importance of integrity, preparation, and putting others first.
Those same values guide every client relationship today.
When you work with Flanagan Insurance Services, you're working with someone committed to doing what's right—not what's easiest.
Working Together with Trusted Professionals
I proudly partner with
✔ Financial Advisors
✔ CPAs
✔ Tax Professionals
✔ HR Professionals
✔ Attorneys
to help clients navigate healthcare decisions before and during retirement.
Staff Members
Main Location (map)
Chad Flanagan
