About the role
We are looking for a Founding Account Executive with 3-7 years of experience to help build Raindrop's sales motion from the ground up. Raindrop is the monitoring platform for AI agents — think "Sentry for AI" — and we're growing so fast that inbound is coming in quicker than we can handle it. You'll sell a deeply technical product to AI engineers, engineering leaders, CTOs, and founders, owning the full sales cycle from outbound through close. You don't need to be an engineer, but you must be able to speak the language credibly and build genuine trust with technical buyers. This is a rare opportunity to join a 13-person team backed by Lightspeed ($15M seed) and shape how a new category of software goes to market.
What will you be doing?
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Owning the full sales cycle — outbound prospecting, discovery, technical evaluation, procurement, negotiation, and close
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Handling a massive influx of inbound leads while also building repeatable outbound processes
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Running sharp discovery with AI engineers, CTOs, and technical founders to uncover pain and business urgency
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Partnering closely with Raindrop's founders and engineers during technical evaluations and pilots
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Turning patterns from customer conversations into product, positioning, and go-to-market insights that shape the company's future
