Lilypad Insurance has announced the appointment of Rajiv Matta as Chief Innovation Officer to lead innovation across Lilypad’s platform. Matta will strategically drive the application of artificial intelligence and emerging technology to enhance Lilypad’s underwriting, distribution and product development in the coastal P&C market.

As Chief Innovation Officer, Rajiv Matta will lead the continued advancement of Lilypad’s AI-native approach, integrating artificial intelligence and technology to meet the unique needs of customers in coastally exposed geographies through customized policies. In this role, he will help shape Lilypad’s innovation roadmap to modernize how the company delivers efficient and effective solutions across homeowners and businesses.

Matta brings more than 20 years of specialty insurance experience across large carriers, reinsurers and managing general agencies, with a track record spanning new product launches, program management and M&A-driven growth. He most recently served as Chief Innovation Officer at Millennial Specialty Insurance, a technology-driven MGA within The Baldwin Group, a publicly traded specialty insurance distribution platform. Prior to that, he led the international property and specialty business at Assurant, a Fortune 300 carrier, overseeing seven product lines across 12 countries.

“Rajiv joins us at an inflection point for the coastal insurance market,” said Sid Jha, Chairman and CEO of 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.”

A recognized voice on AI’s role in reshaping insurance, Matta has argued publicly that AI adoption, ownership of proprietary data, and evolving capital appetite are converging to redraw competitive lines across the industry as carriers, reinsurers and MGAs still running disconnected systems cede ground to forward-looking peers. In his role at Lilypad Insurance, Matta will drive the firm’s continued commitment to tapping the full potential of AI to deliver comprehensive support and coverage solutions to customers in high-risk coastal areas.

“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,” Matta said. “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.”

Matta holds two machine learning patents, including the application of ML to optimize insurance distribution and the application of ML 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.

Matta’s appointment continues a run of senior hires at Lilypad and its MGA, which recently added Andy Flanagan as Vice President of Claims and Tyler Warden as Head of Sales. Both were formerly at Kin Insurance.

As Vice President of Claims, Flanagan will lead end-to-end claims operations to improve efficiency, compliance, and customer experience. He brings more than 20 years of experience in the insurance sector including past leadership roles at Allstate and Nationwide Insurance. Flanagan has experience in property and casualty claims, operational performance improvement, and employee engagement, as well as building operational efficiencies from training programs to process automation.

Tyler Warden, Head of Sales, will focus on strengthening and expanding agency engagement across priority states, supporting the company’s next phase of growth. With over 10 years of experience across insurance, insurtech, and sales leadership, Warden has a strong track record of building and scaling distribution teams, launching new go-to-market initiatives, and driving growth in highly regulated markets.

These appointments reflect Lilypad’s continued investment in scaling its leadership team as demand for innovative insurance solutions grows amid rising climate-driven disasters.

For more information about Lilypad Insurance Holdings, please visit www.lilypadins.com.