Proposal Automation Software isn't One-Size-Fits-All ✹ Jasper Cooper, CEO of AutoRFP.ai

We cover where the human in the loop is disappearing, when buying software beats running on Claude and a spreadsheet, how to answer a CISO who has banned AI, and what happens to win rates in 2027 when every team automates at once.This is Jasper's second time on The stargazy Brief. He spent more than a decade running enterprise sales and RFP processes before building AutoRFP.ai, and has worked with over 200 companies moving off legacy systems.✹ Test the import of your messiest documents and the branded export before you trust the middle✹ Go/no-go, first drafts, and fact-checking are already automated; SMEs are often a safety blanket teams do not need✹ Volume and FTE-hours are the two signals that tell you when to buy✹ Zero data retention, zero training, and data residency are the questions that unblock AI in a compliance-heavy saleFor heads of proposals, CROs, and solution engineering leaders deciding what to buy and why the last tool did not fix what it was supposed to.