Account Executive

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 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.

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

• 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