As the Chief Growth Officer at The Zebra, the trusted partner for American insurance customers, Stuart Winchester leads growth and marketing, overseeing a nine-figure paid acquisition program.

He joined in July 2024 through The Zebra's acquisition of Marble, the digital insurance wallet he founded and ran as CEO. Before Marble, Stuart was General Manager of Insurance at Better.com, where he launched and led Better Cover, the company's national property and casualty practice. Prior, he ran General Assembly's flagship New York campus through a turnaround across marketing, operations, and sales ahead of the company's acquisition by the Adecco Group, and began his career on the founding team at Accordion.

Stuart has been a licensed property and casualty agent since 2018 and a licensed life agent since 2022. He is regularly quoted in Forbes, Time, Fortune, and Business Insider, and writes independently on insurance and growth at shwinchester.com. He holds a BA and MA from Trinity College Dublin.