Reverse-Engineering the AI Buyer — Aliisa Rosenthal, Acrew Capital
Aliisa Rosenthal, who helped OpenAI grow from several million to several billion dollars in revenue, shares lessons on selling AI tools to businesses.
She says OpenAI made many mistakes early on: they built for the loudest customers with expensive enterprise software, but when they later launched cheaper self-service options, growth accelerated dramatically and cannibalized enterprise sales. Her advice to founders is to first automate as much as possible, then hire people only where the system falls short—not the other way around. She also warns against giving buyers "homework" to do, letting pilot projects become free sales processes, and recommends automating security questions that often kill deals.
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