Jeff Winkle currently serves as the Director of Product for AI and Automation at CertifID since September 2025. Prior to this role, Winkle co-founded Painless, which focuses on creating AI infrastructure for title companies and was acquired by CertifID in 2025. From 2021 to 2024, Winkle co-founded and led operations at Thirdwork, a platform specializing in fractional talent for blockchain, AI, and fintech sectors. Winkle's experience includes a tenure as Strategy & Operations Lead at Lemonade, contributing to the successful launch of the Car Insurance product, and roles in business operations at CPOHQ and Knoetic AI, as well as technical and risk consulting at TD and FRG. Winkle began the career with a sales operations internship at Hewlett Packard Enterprise. Academic credentials include a B.S. in Economics from the University of North Carolina Wilmington and studies in European Economics & Finance at the University of Valencia.
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