Jerry Gupta

Jerry Gupta is a tech and business leader with a proven track record in driving digital innovation, scaling AI initiatives, and spearheading enterprise-wide product development. He is serial entrepreneur and investor. As a member of the Founding Team and Head of Insurance & AI Products at Armilla, a venture-backed AI Risk Management and Insurance company, Jerry led the development of AI risk management products. Previously, as SVP at Swiss Re, Jerry led the P&C R&D function, showcasing his capability in identifying and assessing emerging risks and developing robust, data-driven methodologies. His executive tenures at Amazon, leading customer experience functions, and at Liberty Mutual, where he was instrumental in launching their Innovation and Venture groups, highlight his expertise in fostering innovation, managing large-scale operations, and driving technology-enabled business transformation. Jerry excels in leading both technical and business teams, bridging the gap between data science and strategic business outcomes. An experienced data science and tech practitioner, he also cultivates future tech leaders through executive education on Artificial Intelligence at MIT and London Business School. His advisory roles for global start-ups further demonstrate his strategic influence. Jerry holds an MBA from MIT Sloan, a Master’s in Predictive Analytics from Northwestern University, and an MS in Computer Science from Bentley University, providing a strong foundation for his data-centric and technology leadership.