Kaaro is building AI agents for the manual work that still runs railroads, from paperwork and data entry to incident reporting, billing, and other operational workflows that still move through phone calls, email, and tribal knowledge. The founders are second-generation railroaders who have known each other for over a decade. Before Kaaro, they dropped out of Waterloo and UBC at 18 to join Toma (YC W24, a16z-backed) as its first two engineers, where Sai led product and growth and Gautham led infrastructure and reliability as the company scaled from roughly 20 customers to hundreds. A few months in, Kaaro is already working with Canada’s largest railroad, CPKC, in late conversations with CN, and building with Gulf & Ohio Railways, a collection of four smaller railroads.