About Marcus Whitfield

I spent 16 years pricing risk for a major Midwest insurer. Then I realized the people who needed me most were the ones who never got to talk to an underwriter.

I grew up in Chicago's South Shore. My dad was a CTA bus driver. My mom worked nights at a hospital cafeteria. They had insurance through work, but they never understood what they were paying for. When I got into the industry, I saw that same confusion everywhere.

I left underwriting in 2017. Not because I hated the industry—I didn't. Insurance is necessary. But I hated how the good stuff was hidden behind jargon and fine print.

So I started CoverageCheckr. No sales. Just analysis. I help you review your coverage, find the gaps, and tell you what to fix.

My Career