Lilypad Insurance has appointed Rajiv Matta as chief innovation officer, tasking him with leading the build-out of the firm’s AI-driven strategy across underwriting, distribution and product development in the coastal property and casualty market.
In the newly created role, Matta will oversee the development of Lilypad’s AI-native platform, which targets homeowners and commercial risks in coastally exposed geographies. His remit includes integrating artificial intelligence and emerging technologies into core underwriting workflows, tailoring coverage for high-risk coastal areas and updating how the company delivers products to agents and policyholders.
Lilypad is positioning AI as a foundation technology rather than an add-on, with Matta expected to shape the company’s innovation roadmap and set priorities around data ownership, automation and risk selection. For insurance professionals, the move reflects a wider shift in catastrophe-exposed books, where carriers are looking to supplement traditional cat modeling and reinsurance structures with more granular, real-time data on property condition, location and exposure.
“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.”
Jha said the gap between carriers that have operationalized AI and those still running “isolated pilots” is widening, with implications for underwriting performance and distribution efficiency.
Matta has more than 20 years of experience in specialty insurance across carriers, reinsurers and managing general agencies. He most recently served as chief innovation officer at Millennial Specialty Insurance, a technology-focused MGA within The Baldwin Group, where he worked on product launches and program development. Before that, he led the international property and specialty business at Assurant, overseeing seven product lines across 12 countries for the Fortune 300 insurer.
His career has included program management and M&A-driven expansion, experience Lilypad is likely to draw on as it scales its coastal portfolio and negotiates with capacity providers. Matta has also been an active commentator on the use of AI in underwriting, arguing that competitive advantage will depend on carriers’ ability to control high-quality proprietary data and embed machine-learning tools into day-to-day decision-making rather than keeping them in pilot mode.
“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.”
Matta’s arrival follows a series of senior appointments at Lilypad and its MGA arm as the group looks to build out its presence in coastal P&C.
Andy Flanagan has joined as vice president of claims, having previously held leadership posts at Allstate and Nationwide. He will oversee end-to-end claims operations, with responsibility for efficiency, regulatory compliance and customer experience. Lilypad said Flanagan brings experience in property and casualty claims, operational performance improvement and process automation.
The company has also hired Tyler Warden as head of sales. Warden, who previously worked at Kin Insurance, will focus on strengthening and expanding agency relationships in priority coastal states and supporting Lilypad’s distribution strategy. His background spans more than a decade in insurance, insurtech and sales leadership, including work on building distribution teams and launching go-to-market initiatives in regulated markets.
The appointments come as coastal property insurers continue to grapple with higher catastrophe losses, climate-related volatility and shifting reinsurance terms. In several US coastal states, capacity has tightened in recent years, and supervisors and rating agencies have increased their scrutiny of how carriers model and manage hurricane, wind and flood exposure.
Against that backdrop, carriers and MGAs active in coastal business have been re-examining risk selection, pricing adequacy and capital deployment, with a growing number turning to granular data and AI-based tools to differentiate between risks within exposed zones.
Lilypad’s latest hires indicate that the company is betting on technology-enabled underwriting, experienced claims management and targeted distribution as it competes for coastal homeowners and commercial accounts.
How effectively it combines AI-driven insight with traditional catastrophe modeling, reinsurance support and regulatory engagement will be closely watched by brokers and other market participants looking for durable capacity in high-hazard coastal regions.
