Anthony R. O’Donnell // September 19, 2025 
(The Plymouth Rock building in Boston. Source: Plymouth Rock Assurance.)
“We’re at a really big inflection point for the industry, more so than we’ve ever been at,” says Andrew Leeds, Chief Claims Officer for Homeowners’, Plymouth Rock Assurance (Boston). He recalls starting out in an era defined by paper files, with the mantra that “if it’s not in the file, it doesn’t exist.” Over the decades, those files have moved from cabinets to PCs to the cloud, but the process has remained the same: a massive store of unstructured data, largely unreadable by