Earlier this year, the "SaaSpocalypse" wiped out something like $2 trillion of SaaS market cap in a matter of weeks — so I sat down with Tony Gentilcore, co-founder of Glean and formerly one of the minds behind Google Search and Chrome, to figure out what's actually happening to software in the agent era.
We get into a lot: why Tony thinks outcome-based pricing (the model Sierra and Decagon are famous for) won't survive, and why companies will drift back toward per-seat. Why the "no Chinese models" rule every enterprise swears by tends to evaporate the moment finance sees the token bill — and why Nemotron, GLM, and Kimi are already good enough to matter. The story behind Sam Altman reportedly telling VCs that if they backed Glean, OpenAI didn't want them as investors (Tony's reaction: "we took it as very flattering").
We also dig into the messier reality of AI at work — how it's saving employees around 11 hours a week while quietly costing them 6 back in what Tony calls "bot sitting and bot shitting," why hard token caps on engineers don't change behavior, how CTOs are blowing through their annual token budgets a quarter into the year, and why the roles of product manager, designer, and engineer are collapsing into one.
If you care about where software, pricing, and enterprise AI are all heading, this one's worth your time.
