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 Jorn van Dijk), Speak (Andrew Hsu), Notion (Akshay Kothari) and more.

Your Focus

• Own the end-to-end recruiting function: sourcing, outreach, interviewing, coordination, closing.
• Build a world-class top-of-funnel engine through relentless outbound sourcing, referrals, content, and other creative recruiting tactics
• Help make the company a magnet for top talent by building a reputation for talent density
• Track and analyze recruiting metrics (pipeline, offer acceptance rates, time-to-hire) to inform hiring strategies

Ideal Candiate

• Has recruited strong engineering teams, ideally at high-growth startups or AI / dev tool companies.
• Proven ability to source, engage, and close standout engineering candidates in competitive markets.
• Understands technical talent deeply and has strong instincts for evaluating engineering profiles.
• 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 work from day one.
• Must be in person in San Francisco (or willing to move)