The Idea: In late 2023, Bret Taylor walked away from one of the most powerful jobs in tech. He'd been co-CEO of Salesforce, chairman of Twitter (where he green-lit Elon's takeover), and most recently chairman of OpenAI's board (where he helped engineer Sam Altman's return after the November 2023 coup). He could have done anything next. Instead, he started an AI company with Clay Bavor, a 17-year Google veteran who most recently led Google Labs. Their bet was specific - customer service is a $400B market still mostly handled by humans on phones, and AI agents that can actually reason and take action would eat that market faster than anyone realised. They didn't want to sell software for humans to use. They wanted to sell labour. This was the beginning of Sierra.
The Execution:
The lesson? Outcome-based pricing is the unlock for AI agents. When you charge per resolved ticket instead of per seat, customers can actually feel the ROI - and they keep paying. Sierra didn't invent agents, but they were one of the first to align their pricing with the value those agents create. That single decision is why they're growing several times faster than the rest of the category.