Founding Account Executive

About Raindrop

Raindrop 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), 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, 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 an Account Executive to help build our sales motion from the ground up.

You’ll sell a deeply technical product to engineering teams, working directly with AI engineers, engineering leaders, CTOs, and founders. You’ll own the full sales cycle, from identifying accounts and running discovery through technical evaluation, security, procurement, and close.

You do not need to be an engineer. You do need to be technically curious, ask sharp questions, understand ambiguous systems and workflows, and build genuine trust with engineers.

This is not a traditional SaaS sales role. You’ll work closely with Raindrop’s founders, engineers, and customers to shape how we sell, whom we sell to, and what we build.

Your Focus

• Own the full sales cycle, from outbound and discovery through evaluation, procurement, negotiation, and close
• Build relationships with AI engineers, engineering leaders, CTOs, and technical founders
• Run sharp discovery that uncovers both technical pain and business urgency
• Understand customers’ AI systems, production workflows, evaluation processes, and monitoring challenges
• Partner closely with engineering during technical evaluations and pilots
• Navigate security, legal, and procurement without losing momentum
• Build repeatable outbound, discovery, qualification, and closing processes
• Turn patterns from customer conversations into product, positioning, and go-to-market insights
• Help define our ideal customer profile, sales motion, and future GTM team

Ideal Candidate

• Proven ability to close technical B2B software deals
• Experience selling to engineers, technical leaders, or other highly technical buyers
• Strong discovery skills and a genuine interest in understanding how customers’ systems work
• Able to translate technical pain into clear business impact
• Curious, low-ego, and comfortable admitting what you don’t know
• Fast learner who can become credible on APIs, infrastructure, AI systems, and developer workflows
• More interested in solving the customer’s problem than running a rigid sales playbook
• Comfortable operating quickly with ambiguity and incomplete information
• Willing to prospect, build process, unblock deals, and do whatever else the role requires
• Interested in AI products and developer tools, ideally through prior work or hands-on personal use
• Excited to work directly with company leadership and own high-impact work from day one
• 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 technical founding AEs and sales engineers who have moved into closing roles.

You’ll Thrive Here If

• Engineers leave your calls feeling understood, not sold to
• You ask questions before pitching
• You can move between technical details and executive-level business outcomes
• You enjoy figuring out a sales process rather than inheriting one
• You want direct ownership, fast feedback, and a meaningful role in shaping the company