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.
Your FocusOwn 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
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 IfEngineers 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