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Account Executive

Raindrop
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Hybrid (San Francisco, CA)$120k - $140kFull-timePosted 2mo ago

About the role

Account Executive role at Raindrop, a YC-backed monitoring platform for AI agents. Own full sales cycle from outbound to close, selling a deeply technical product to engineering teams and technical buyers in San Francisco or with relocation.

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 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

Qualifications

  • 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
  • Open to technical founding AEs and sales engineers who moved into closing roles

Skills

Required:Full sales cycle managementRelationship building with engineering teamsDiscovery and needs assessment
Nice to have:Technical fluency with AI systems and APIs
Last updated Oct 21, 2026. Interested? Apply on the company site.
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About Raindrop

Sentry for AI Agents

Monitor your AI agents the right way. AI engineers use Raindrop to get alerts about hidden issues and successes in their AI agents. Raindrop sends you alerts when your AI misbehaves and links straight to the events, so you can dig into the conversations or traces, understand the root cause, and fix it, fast.

artificial-intelligenceb2bmonitoringai
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