Founding Account Executive

Raindrop • San Francisco, CA

9d • Onsite

About The Position

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.
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.
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.

Requirements

• 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.

Nice To Haves

• 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

Responsibilities

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed