Bret Taylor’s AI startup Sierra announced Monday it is raising a $950 million funding round led by Tiger Global and GV, pushing its post-money valuation above $15 billion. Combined with existing capital, the raise gives Sierra more than $1 billion to deploy as it pursues what it describes as the “global standard” for AI-powered customer experiences.
Sierra says it has grown from four design partners a couple of years ago to serving more than 40% of the Fortune 50 today. The company reports its agents are handling billions of interactions across tasks such as refinancing mortgages, processing insurance claims, managing returns, and supporting nonprofit fundraising. On the revenue side, Sierra said it reached $100 million in annual recurring revenue in late November 2025, then climbed to $150 million ARR by early February 2026.
Taylor, who also serves as chairman of OpenAI and was formerly co-CEO of Salesforce, has noted that while agentic AI can ultimately lower costs and raise revenue for clients, the initial ramp-up phase carries significant expense. That dynamic surfaced at a recent TechCrunch StrictlyVC event, where Uber CTO Praveen Neppalli Naga said the company “blew through our [AI] budget” shortly after adopting agentic AI tools. He added that results are beginning to materialize — roughly 10% of all code across Uber’s approximately 8,000-person engineering and technical workforce is now generated autonomously, and one team completed a hotel-booking integration in six months rather than the expected year.
Sierra is also expanding its platform beyond customer-facing agents. In April 2026, the company launched Ghostwriter, a tool that lets users describe a need in natural language and then autonomously creates and deploys a specialized agent to handle it.
Taylor has argued that many enterprise software tools go largely unused — employees log into systems like Workday only at onboarding and open enrollment. Sierra’s broader bet, backed by this latest round, is that AI agents could eventually replace the need to navigate those complex systems altogether.
Source: TechCrunch