Raindrop

Sentry for AI Agents

About the role

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.

Why It Matters

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.

Our Investors

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.

Your Focus

• Embed with our customers to get them up and running on Raindrop
• Own customer problems end-to-end, debugging across their agents and our platform
• Turn what you learn on the ground into product feedback that shapes our roadmap

Ideal Candidate

• Top 0.1% communicator who would rather be in front of customers than heads-down all day
• Strong engineer who can read a codebase, debug production systems, and fix customer bugs hands-on
• Interest in AI products + tools (ideally experience building these or an avid user)
• Growth mindset
• Willing to do whatever it takes to solve a problem
• Excited to work closely with leadership and own high-impact work from day one.
• Must be in person in San Francisco (or willing to move)