Raindrop Raises $15M to Monitor AI Agent Failures in Production

Raindrop, a San Francisco-based monitoring platform for AI agents, has secured $15 million in seed funding led by Lightspeed Venture Partners, positioning the company to meet surging enterprise demand as autonomous AI agents take on increasingly complex and critical tasks.

The round attracted significant participation from leading figures in the AI ecosystem. Figma Ventures and Vercel Ventures joined as institutional investors, while notable founders from Replit, Cognition, Framer, Speak, and Notion contributed as angel investors. Y Combinator also participated in the round.

The diverse investor group reflects broad recognition that monitoring infrastructure represents a critical missing piece as AI agents move from experimental deployments to production environments handling millions of daily interactions.

Modern AI agents now reason for extended periods, connect to multiple tool servers, and operate autonomously for hours at a time. Traditional testing methodologies cannot adequately validate these complex, long-running processes.

CEO Zubin Koticha explained that conventional evaluation methods leave engineering teams unable to discover or track issues as they occur in production. This creates a dangerous blind spot as AI agents are increasingly deployed in high-stakes sectors like healthcare and financial services, where failures can have business-critical or even life-threatening consequences.

Recent high-profile incidents underscore the risks. ChatGPT has been reported encouraging users to discontinue medication, while Air Canada faced legal action after its chatbot promised refunds the company could not honor. These failures demonstrate how AI systems can malfunction in ways that are difficult to predict or catch with traditional quality assurance approaches.

Raindrop establishes a new standard for monitoring AI agent behavior through small, custom models that adapt to the unique characteristics of each AI product. This approach enables engineering teams to track signals that were previously invisible with legacy monitoring tools.

Previous generation monitoring platforms typically offered only basic metrics like latency, token usage, toxicity scores, or user sentiment. These generic measurements rarely revealed actual errors in agent behavior or decision-making processes.

Raindrop's platform allows customers to define custom signals specific to their products, such as UI Aesthetic Complaints or Agent Stuck in a Loop, alongside default signals like User Frustration. Teams can then monitor incident rates across millions of events and receive Sentry-style notifications when problems exceed defined thresholds.

Beyond alerting, Raindrop deploys AI agents in the background to continuously triage and investigate potential issue patterns. When the system detects a new problem, such as an agent encouraging toxic user behavior or making factual errors, Raindrop automatically collects information and generates step-by-step explanations of what occurred.

This automated investigation capability significantly reduces the time engineering teams spend diagnosing production issues, allowing them to move quickly from detection to resolution.

Bucky Moore, Partner at Lightspeed Venture Partners, noted that his firm invested because Raindrop correctly predicted that robust monitoring would become the most crucial element for building reliable agents. The company has already achieved rapid adoption among leading AI engineering teams.

Raindrop currently works with frontier AI customers processing millions of events each day, helping to discover, monitor, and resolve critical issues in production environments. This early traction demonstrates strong product-market fit in a rapidly expanding category.

The company was founded by Zubin Koticha, Ben Hylak, and Alexis Gauba. Koticha previously co-founded Opyn, a decentralized finance options platform that was acquired by Coinbase after facilitating over $15 billion in trading volume. Hylak spent four years on Apple's Human Interface team working on visionOS before co-founding Raindrop.

The team brings together deep expertise in building complex systems, financial infrastructure, and consumer-facing technology products.

The $15 million in seed funding will enable Raindrop to scale operations and meet growing enterprise demand. The company plans to expand its engineering team, enhance its monitoring capabilities, and establish itself as the default observability solution for production AI agents.

Raindrop positions itself as Sentry for AI agents, referencing the widely adopted error tracking platform used by software developers worldwide. The comparison signals the company's ambition to become similarly essential infrastructure for AI application development.

The successful fundraise highlights growing recognition that AI agents require fundamentally different monitoring approaches compared to traditional software. As these systems take on more autonomous responsibilities and longer-running tasks, the ability to detect and diagnose silent failures becomes increasingly critical.

For enterprises deploying AI agents in customer-facing roles or mission-critical operations, platforms like Raindrop may soon become as essential as traditional application performance monitoring tools. The company's early momentum suggests the market agrees with this assessment.