Reverse-Engineering the AI Buyer — Aliisa Rosenthal, Acrew Capital
Aug 26, 2026 · 19:10
Aliisa Rosenthal, who helped take OpenAI's enterprise business from a couple million to several billion in revenue, argues founders should build the automated sales machine before hiring humans. ChatGPT launched with no enterprise features; nine months later they shipped an expensive product, but self-serve cannibalized it four months on. Advice: capture phone numbers at signup, reply to every inbound (10,000 a day), never give buyers homework, avoid pilots via reference calls, data evals, or 90-day opt-outs. $60 per user per month was too high; a low base fee plus usage spread. Automate security, don't pull up-market, hire AI-native sellers when buyers need contact, and use forward deployed engineers sparingly—scarce but sticky. First 10 customers should be handpicked design partners, and POCs aren't self-serve.
