Arman Kumaraswamy

Arman Kumaraswamy is cofounder of The Context Company, which analyzes customer conversations with production AI agents to find where those agents lose users or money, then helps teams ship and measure fixes. With childhood friend Rohil Agarwal he is based in San Francisco and joined the YC Fall 2025 batch as a two-person founding team.

Friends since middle school

On the YC company page Kumaraswamy and Agarwal say they have been best friends since sixth grade. Kumaraswamy studied computer science and math at the University of Florida and engineered at Mintlify, Apten, RevisionDojo, and Solace Health. Agarwal studied EECS and business in UC Berkeley's M.E.T. program and worked on Gmail Intelligence at Google, including intent detection models touching tens of billions of daily emails.

Silent agent failures as the product

Their pitch is that classic observability shows latency and stack traces while missing quiet reasoning and tool-call breakdowns that only show up across many customer threads. At Mintlify, Kumaraswamy has said he worked on the public-facing AI agent and cut failure rates sharply while partnering with enterprise design partners. The Context Company wraps that lesson into a product that clusters patterns by account, lets engineers pull the underlying traces from an IDE through MCP, and gives customer-success teams a way to step in before a complaint lands.