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Raindrop
Monitoring platform for detecting silent AI agent failures
About Raindrop
Raindrop.ai is an applied AI research company based in San Francisco that provides a monitoring platform specifically designed for AI agents. The company was founded in 2023 by Ben Hylak, Zubin Koticha, and Alexis Gauba. The founding team's practical experience building their own coding agent and encountering silent failures during its production phase led to the creation of Raindrop. Gauba and Koticha were second-time founders whose previous company, Opyn, was acquired by Coinbase, while Hylak previously worked as an engineer on Apple's Human Interface Design team.
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Positioning itself as "Sentry for AI agents," Raindrop addresses the problem that traditional testing methods cannot handle the complexity of modern AI agents, which can reason longer and run autonomously for hours. The platform is designed to detect silent AI agent failures in production, such as giving incorrect information, forgetting context, or deviating from its intended persona, which are often invisible to traditional monitoring tools. It provides engineering teams with alerts when an AI misbehaves, allowing them to investigate the root cause through conversation traces and tool calls. Raindrop uses small, custom AI models that adapt to each AI product, enabling the monitoring of previously invisible signals like "User Frustration" or custom-defined alerts such as "Agent Stuck in a Loop". Key features include a "Deep Search" function to find specific issues in production data using natural language, automated issue discovery, and an A/B testing platform called Raindrop Experiments to validate fixes.
The company's business model targets AI engineering teams and enterprise clients. In December 2025, Raindrop announced a $15 million seed funding round led by Lightspeed Venture Partners. The funding round included participation from Figma Ventures, Vercel Ventures, Y Combinator, and the founders of notable tech companies like Replit, Cognition, and Notion. This capital is intended to meet growing enterprise demand and establish the company as a primary monitoring solution for production AI agents.
At a glance
- Status
- Operational
- Headquarters
- San Francisco, United States
- Employees
- 16
- Open positions
- 1
- Dealroom signal
- 0.0/100
- Industry
- Enterprise Software
- Sector
- AI, MLops, Privacy-Enhancing Technologies, AI Data Preparation and Generation
- Technology
- Artificial Intelligence
- Business model
- SaaS
- Client focus
- b2b
Latest news
Press, funding announcements and product moves mentioning Raindrop.
Funding history
Company financing events and reported valuations.
| Deal type | Date | Amount | Valuation | Investors | Source |
|---|---|---|---|---|---|
| SEED✓Equity / VC | Dec 2025 | $15M | $60M | Andrew Hsu · Koen Bok · Lightspeed Venture Partners · Akshay Kothari | ↗ |
Growth signals
Latest recorded traffic for Raindrop is 71K monthly website visits, up 82.1% over the last three months.
Open positions
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Investors
From Dealroom's funding and investor records, grouped by the round each investor first entered.
Seed11 investors entered at this stage
Lightspeed Venture Partners
Andrew Hsu
Koen Bok
Akshay Kothari
Vercel
Walden Yan
Y Combinator
Amjad Masad
Jorn van Dijk- FVFigma Ventures
Michele Catasta
Other known investors1 additional known investor
Pioneer Fund
Source: Dealroom Talent Intelligence.
Global footprint
team presence
Market sentiment
An AI-synthesised read of the highest-engagement posts about Raindrop on X, ranked by likes and reposts, corporate channels excluded.
Reading the room on X — pulling top posts and synthesizing themes…
Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour
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