Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100 and fastest AI companies including Vercel, Speak, Clay, use Raindrop to get alerts about silent failures with their AI agents. Raindrop sends alerts when AI agents misbehave, so AI engineers can dig into the conversations or traces, understand the root cause, and fix it, fast.
AI agents fail constantly in ways both hilarious and terrifying. Regular software throws exceptions. But AI agents fail silently, leaving engineers with almost no visibility into how their agents are actually performing.
The current status quo is sifting through millions of logs and trying debug flaky evals that just aren't matching real world results. Evals are like unit tests, they confirm your model got specific test cases right. But in the real world agents call thousands of tools, run for hours, and encounter millions of unpredictable actions.
That’s where Raindrop comes in. It learns the unique shape of each AI agent’s issues. Starting from presets like Laziness, Forgetting, or Task Failure, to automatically tuning itself to each agent and discovering unknown unknowns.
With one click of a button, AI engineers start tracking issues or topics across 100% of their production data. They can see frequency over time, how many users are affected, relevant properties and more.
In order to process hundreds of millions of events, we gradually train small, custom models, private to each company, that learn to uniquely understand how their product is used.
As part of the early team, you’ll play a fundamental role in shaping the company - from making strategy and product decisions, to helping scale the team, to shaping the future of AI agents.
We’re backed by incredible investors including Lightspeed and leading AI companies including Figma Ventures, Vercel Ventures, founders of Replit (Amjad Masad and Michele Castata), Cognition (Walden Yan), Framer (Koen Bok and Jorn van Dijk), Speak (Andrew Hsu), Notion (Akshay Kothari) and more.
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.
Salary
$130,000 - $200,000
Location
San Francisco, CA
Experience
3+ years
Total raised
$15.0M
Last stage
Seed
Investors
No applications, no recruiter spam. Just the intro.
A few questions to make sure this role is the right shape for you. Two minutes.
I write the intro, send it to the founder, and handle the back-and-forth.
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.