About the Role

Raindrop is the monitoring platform for AI agents. Engineering teams at Fortune 100 companies and leading AI companies including Vercel, Speak, and Clay use Raindrop to detect silent failures in production.

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.

Why It Matters

AI agents fail constantly in ways both hilarious and terrifying.

Regular software throws exceptions. AI agents often fail silently, leaving engineering teams with little visibility into how their systems are actually performing.

The current status quo is manually reviewing millions of logs and debugging evals that don't match real-world behavior. Evals are like unit tests: they confirm that a model handled specific test cases correctly. But production agents call thousands of tools, run for hours, and encounter millions of unpredictable actions.

Raindrop learns the unique shape of each AI agent's issues. Engineering teams can track failures and behaviors across 100% of their production data, understand how frequently they occur, see which users are affected, and investigate the underlying conversations and traces.

As an early member of the GTM team, you'll play a fundamental role in bringing this new category of software to market.

Our Investors

We're backed by Lightspeed and leading AI companies and founders, including Figma Ventures, Vercel Ventures, Amjad Masad and Michele Catasta of Replit, Walden Yan of Cognition, Koen Bok and Jorn van Dijk of Framer, Andrew Hsu of Speak, Akshay Kothari of Notion, and more.

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.