Summary
Clay Pavore, co-founder of Sierra, joins Harry Stebbings on 20VC to discuss building one of the fastest-growing enterprise AI companies in the world. Sierra has raised over $1.5 billion, carries a valuation approaching $16 billion, and counts roughly 40% of the Fortune 50 as customers — handling hundreds of millions of AI-powered customer interactions across service and support use cases.
Pavore draws on 18 years at Google before co-founding Sierra with Brett Taylor in late 2022, and the conversation covers Sierra’s philosophy of investing deep in the technology stack, why they believe the enterprise AI agent market will consolidate into an Uber/Lyft-style duopoly rather than a multi-cloud fragmentation, and how their Palantir-inspired embedded-team go-to-market model has driven outsized enterprise wins.
The episode also explores the competitive implications of Chinese companies’ willingness to do scaled distillation of frontier models, Pavore’s prediction that every engineer will eventually need a $100,000 token budget, and how Sierra has completely overhauled its engineering interview process around AI-native candidates. Some of the company’s most effective engineers are 22 or 23 years old and have grown up building entirely with AI — a shift Pavore sees as a fundamental change in how great software companies will be built.
📺 Source: 20VC with Harry Stebbings · Published July 04, 2026
🏷️ Format: Interview
