Lilypad names Matta Chief Innovation Officer. The coastal insurer says Rajiv Matta will guide its use of AI in underwriting, distribution and product development. Anthony R. O'Donnell // May 19, 2026 (Image source: Lilypad Insurance homepage.) Lilypad Insurance (New York), an admitted property/casualty insurance group focused on coastal property risk, has appointed Rajiv Matta Chief Innovation Officer. Matta will lead the insurer's use of artificial intelligence and emerging technology across underwriting, distribution and product development. Matta joins Lilypad from Millennial Specialty Insurance, a technology-driven MGA within The Baldwin Group, where he served as Chief Innovation Officer. He previously led the international property and specialty business at Assurant, overseeing seven product lines across 12 countries. "Rajiv joins us at an inflection point for the coastal insurance market," comments Sid Jha, Chairman and CEO, Lilypad Insurance. "His hands-on experience building insurance programs at scale, combined with his conviction that AI must be embedded across the full value chain, not bolted on, makes him exactly the kind of leader we need as we expand Lilypad's footprint. The gap between carriers who have genuinely operationalized AI and those still running isolated pilots is widening every quarter, and Rajiv understands that better than most." In his new role, Matta will shape Lilypad's innovation roadmap and support the company's use of AI and proprietary data in underwriting, pricing and distribution for coastally exposed markets. Lilypad says its approach uses proprietary AI models and satellite-derived data to support underwriting decisions. "Lilypad is built on a conviction I've held for years: that AI isn't a feature you add to an insurance company, it's the foundation you build on," comments Matta. "The coastal market is at a structural turning point. The insurance companies who will define the next decade are the ones doing the hard work now to own their data, automate intelligently and price risk with precision. I'm here to help Lilypad achieve that goal." Leadership Team Expansion Matta's appointment follows other recent senior hires at Lilypad and its MGA, including Andy Flanagan, VP, Claims, and Tyler Warden, Head of Sales. Flanagan previously held leadership roles at Allstate and Nationwide, while Warden brings experience in insurance, InsurTech and sales leadership. Matta holds two machine learning patents, including one involving the use of machine learning to optimize insurance distribution and another to predict risk variables. He holds an MBA from the University of North Carolina at Chapel Hill, a Master of Science in environmental engineering from Clemson University and a Bachelor of Science in chemical engineering from the University of Mumbai.

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