Raindrop

Sentry for AI Agents

Raindrop is the monitoring platform for AI agents. Engineering teams at some of the fastest growing AI companies including Replit, Speak, Clay, and more 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 Joen van Dijk), Speak (Andrew Hsu), Notion (Akshay Kothari) and more.

Your Focus

• Improve core business operations across finance, legal, compliance, billing, recruiting, and internal operations
• Automate as much as possible using AI tools to help the company run more efficiently
• Build dashboards, models, and processes that improve visibility into the business and help the team make better decisions.
• Help build and run the processes that support trust, compliance, and operational readiness as the company scales.
• Own key operational relationships with external partners and vendors
• Drive contracting and deal workflows end-to-end so nothing slows down a customer close

Ideal Candiate

• Knows how to balance speed with rigor and attention to detail.
• Proven ability to operate across multiple functions in a fast-moving environment.
• Strong communication skills.
• Aggressive user of AI tools and automation; always looking for ways to make work more efficient and scalable.
• Growth mindset
• Highly organized and reliable.
• Willing to do whatever it takes to solve a problem
• Excited to work closely with leadership and own high-impact operational work from day one.
• Must be in person in San Francisco (or willing to move)