ABOUT RAINDROP Raindrop http://raindrop.ai/ is the monitoring platform for AI agents. Engineering teams at Fortune 100s and the fastest-growing AI companies (Vercel, Speak, Clay) use it to catch silent failures in production. When an agent misbehaves, Raindrop alerts the team, links to the trace, and surfaces the root cause so they can fix it fast. With Raindrop 2.0 (Self-Healing Agents) https://www.raindrop.ai/blog/introducing-raindrop-2/, the loop closes itself: your coding agent fixes it, and the fix becomes an eval to prevent regressions. 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 to 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've raised $50M total https://www.raindrop.ai/blog/series-a/, led by CRV, with backing from Lightspeed, Figma Ventures, Vercel Ventures, and the founders of Replit (Amjad Masad, Michele Catasta), Cognition (Walden Yan), Framer (Koen Bok, Jorn van Dijk), Speak (Andrew Hsu), and Notion (Akshay Kothari). We're hiring a Sales Development Representative to build our outbound pipeline engine from the ground up. You'll prospect into engineering teams: AI engineers, engineering leaders, CTOs, and technical founders. Developers ignore generic outreach, so this role is about research, relevance, and writing, not dialing through call lists. You'll find the companies shipping AI agents, figure out where their systems are failing, and start conversations that engineers actually want to have. This is not a traditional SDR role. You'll work directly with Raindrop's Head of GTM and founders to shape our outbound motion, and you'll be first in line for an AE path as the team grows. YOUR FOCUS - Build and own outbound pipeline: research accounts, identify the right people, and book qualified meetings for our AE team - Build AI-powered outbound systems that personalize at scale. High volume, but every email reads like it was researched by hand - Run signal-based prospecting (GitHub activity, product launches, incident postmortems, hiring patterns, AI agent releases) instead of spray-and-pray sequences - Qualify inbound leads and route them fast - Track what's working: reply rates, meeting rates, channel performance, and messaging experiments - Turn patterns from prospect conversations into ICP, positioning, and messaging insights - Help define the outbound playbook the future SDR team will run IDEAL CANDIDATE - Proven ability to generate cold pipeline: meetings booked from accounts with no prior relationship, in markets where your network doesn't help - Exceptional written communication; your emails and DMs are the first impression of Raindrop - Builds with AI, not just uses it: agents, enrichment pipelines, Clay-style workflows that make one person prospect like a team of five - Technically curious: genuinely wants to understand how AI agents work, what a trace is, and why silent failures matter - Experience prospecting into engineers, technical leaders, or developer audiences, or the instincts to know why devs hate typical sales outreach - Resilient, self-motivated, and consistent. Outbound is a volume game played with precision - Coachable, with examples of feedback that changed your numbers - Highly organized: pipeline hygiene, follow-ups, and CRM discipline without being told - Ambitious: wants to earn a path to AE and help build the GTM team - Interested in AI products and developer tools, ideally through hands-on personal use - Must be in person in San Francisco or willing to relocate Strong candidates may come from developer tools, observability, infrastructure, cloud, data, security, APIs, or AI/ML tooling. We're also open to career-changers with technical backgrounds who want to break into sales. YOU'LL THRIVE HERE IF - Engineers reply to your cold emails asking to learn more, not to unsubscribe - You use AI to send 200 emails that each read like you sent 10 - You treat outbound like a product: experiment, measure, iterate - You want direct ownership, fast feedback, and a real path to closing deals - You get energy from starting conversations no one asked for