Raindrop

Raindrop is the observability platform for AI agents — think Sentry or Datadog, but purpose-built for the unique challenges of AI systems in production. Engineering teams at Fortune 100 companies and leading AI companies including Vercel, Speak, and Clay use Raindrop to detect silent failures, hallucinations, and misbehaviors in their AI agents.

Unlike traditional software that throws exceptions, AI agents often fail silently, leaving engineering teams with little visibility into how their systems are actually performing. Raindrop learns the unique shape of each AI agent's issues, sends alerts when something goes wrong, and links straight to the underlying conversations and traces so teams can understand root causes and fix them fast.

Backed by Lightspeed with a $15M seed round, along with investors including Figma Ventures, Vercel Ventures, and prominent founders from Replit, Cognition, Framer, Notion, and Speak. Founded in 2023 and part of Y Combinator, Raindrop is defining a new category of software at the intersection of AI and observability.

The team operates out of their North Beach, San Francisco office with an intense, high-energy culture. The company is growing rapidly with inbound demand outpacing their ability to handle it, and they're actively building out their go-to-market team to match.