Account Executive

About the RoleRaindrop 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 MattersAI 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.Your FocusOwn the full sales cycle, from outbound and discovery through evaluation, procurement, negotiation, and closeBuild relationships with AI engineers, engineering leaders, CTOs, and technical foundersRun sharp discovery that uncovers both technical pain and business urgencyUnderstand customers' AI systems, production workflows, evaluation processes, and monitoring challengesPartner closely with engineering during technical evaluations and pilotsNavigate security, legal, and procurement without losing momentumBuild repeatable outbound, discovery, qualification, and closing processesTurn patterns from customer conversations into product, positioning, and go-to-market insightsHelp define our ideal customer profile, sales motion, and future GTM teamIdeal CandidateProven ability to close technical B2B software dealsExperience selling to engineers, technical leaders, or other highly technical buyersStrong discovery skills and a genuine interest in understanding how customers' systems workAble to translate technical pain into clear business impactCurious, low-ego, and comfortable admitting what you don't knowFast learner who can become credible on APIs, infrastructure, AI systems, and developer workflowsMore interested in solving the customer's problem than running a rigid sales playbookComfortable operating quickly with ambiguity and incomplete informationWilling to prospect, build process, unblock deals, and do whatever else the role requiresInterested in AI products and developer tools, ideally through prior work or hands-on personal useExcited to work directly with company leadership and own high-impact work from day oneMust be in person in San Francisco or willing to relocateYou'll Thrive Here IfEngineers leave your calls feeling understood, not sold toYou ask questions before pitchingYou can move between technical details and executive-level business outcomesYou enjoy figuring out a sales process rather than inheriting oneYou want direct ownership, fast feedback, and a meaningful role in shaping the company