About

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The history behind Rosella

I know how hard insurance can be, I’ve been on the other side of it. Once upon a time, my three friends and I decided to run from Key West, Florida, to the Canadian border — 80 marathons in 80 days, raising money for cancer research.

It was nearly impossible to find anyone who would insure us. I spent days reading hundreds of pages of product disclosures, trying to understand what was covered and what wasn’t. I thought I’d finally found the right policy, until page 109 excluded ‘extreme endurance events’ in the fine print. I ended up running uninsured. The one risk my running coach warned me about was my feet – if you get an infection, it’s all over. On day forty, I got that infection. Cellulitis. My feet were so swollen my shoes didn’t fit, and I was having a life-threatening septic attack. But without insurance, I couldn’t afford hospital treatment, so I kept running. That experience showed how disempowering insurance can feel. The process of buying the right policy was confusing, and no one seemed able to place us in a box. Chris and I started this brokerage to change that. We are your partners in risk. You don’t just need someone to sell you a policy – you need a support team of professionals armed with modern technology. People who actually understand your business. As large corporations keep buying up independent brokerages, service gets sacrificed for profit. Customers get less attention, while many small retail brokers rely on relationships over technical skill. We built this firm to fight back, giving SMEs and mid-market American businesses access to world-class expertise and modern technology, with one clear goal: five-star service.

Sean Stuart (CEO of Rosella)

Our founders

Sean’s background is in commercial law/finance, beginning with a full-ride scholarship to the University of Sydney’s globally top-10 ranked law program. The experience instilled five years of rigorous training in analysis and attention to detail - skills he now applies to navigating complex business and insurance matters. Sean spent time as a writer and endurance athlete, publishing two books and completing 80 marathons in 80 days up the East Coast. He still can’t cook.

Sean Stuart

CEO

Chris’s background is in software. He was a founding engineer at an AI platform for bankers, building complex and compliant lending workflows for banks. These skills are now being applied to navigating the complex world of insurance. In his spare time, he's busy updating his birdwatching knowledge to the new lands of Texas.

Chris Dwyer

CTO

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