Our Trusted Carriers

Founder, Cast Iron Insurance

Glen Bailey founded Cast Iron Insurance in 2016 with a simple goal: bring a more personal and advisory-driven approach to insurance. Instead of simply selling policies, Glen focuses on helping clients understand risk and build the right protection around what they’ve worked hard to build.

Born and raised in Northern Kentucky, Glen has lived within a 20-mile radius his entire life and has spent more than two decades building relationships with local families and business owners. His deep local roots shape how he approaches his work, focusing on trust, long-term relationships, and practical advice that helps clients make confident decisions.

Glen’s background and experience have led him to work closely with business owners, particularly contractors and growing manufacturing companies. With family ties to the hardware and lumber industry that served contractors for more than 45 years, he understands the realities of running a business and the risks that come with it.

Clients often describe Glen as having a “teacher’s approach” to insurance. He takes pride in explaining complex coverage issues in a way that makes sense, helping clients understand not only what protection they have, but why it matters. That consultative mindset is what led to the creation of Cast Iron Insurance, an agency built on the belief that strong protection and strong relationships go hand in hand.

Outside of the office, Glen enjoys spending time with his family and staying active in the Northern Kentucky community he has always called home.