About this session

Eighteen months ago, every AI startup with a wrapper and a waitlist was raising at $100M+. The memo was simple: AI market is huge, team is technical, ship fast. That memo is dead. Rory O'Driscoll has been investing at Scale Venture Partners since the mid-90s, backing companies like Bill, Box, and DocuSign before they were obvious. Since 2022, he's written checks into a new wave of AI companies (Tavus, Klarity, Regie, Unwrap) and watched hundreds more pitch. In this session, Rory breaks down what's actually changed in how top-tier VCs evaluate AI companies today vs. early 2025: what metrics matter now that usage data exists, where the bar has moved on defensibility, which categories are overfunded, and what signals separate the AI companies that will endure from the ones that just rode the hype. You'll learn: •What Scale looks for in an AI investment memo today that they didn't require 18 months ago •The categories Rory thinks are still wide open vs. the ones where it's already too late •How revenue quality, retention, and margins are being evaluated differently for AI-native companies vs. traditional SaaS •What Bill, Box, and DocuSign looked like at the early stage, and which AI companies today pattern-match to those bets This is for you if you're a founder raising capital, thinking about your defensibility story, or trying to understand how the best investors are separating signal from noise in AI right now.