Sierra raises $950 million as race for enterprise AI grows more serious

Brett Taylor’s AI startup Sierra has raised a $950 million funding round led by Tiger Global and GV, the company announced Monday, pushing its post-funding valuation above $15 billion. The raise gives Sierra more than $1 billion to work with, capital that the company says it will use to become the “global standard” for AI-powered customer experiences.

Like a lot of AI companies, Sierra has, smartly, been very proactive in promoting its growth in a crowded market. The company says it started with just four design partners two years ago. Today it claims to have more than 40% of the Fortune 50 as clients, and says agents running on its platform handle billions of interactions, from mortgage refinancing to processing insurance claims, managing returns, and supporting nonprofit fundraising campaigns.

In fact, news of the funding follows a continuation of rapid revenue growth as shared by Sierra, which first said it had hit $100 million in annual recurring revenue in late November, then made another post in early February, saying it had reached $150 million in ARR.

This pace reflects the urgency companies have about deploying AI and the costs that come with it. The best outcome for agentic AI is lower costs and increased revenue for customers, but before those returns are realized, the ramp-up phase can be expensive, said Taylor, who also serves as chairman of OpenAI and was previously co-CEO of Salesforce.

This exact scenario came up in a conversation at one of TechCrunch’s StrictlyVC events last week. Praveen Nepali Naga, Uber’s chief technology officer, made it clear in a conversation with this editor, saying that Uber “violated… [AI] Budget” shortly after opening the door to AI tools late last year. He also said the company is starting to see meaningful results.

With a staff of nearly 8,000 engineers and technical workers, about 10% of all code produced at the company is now generated independently, he said, adding that “10% at our scale is huge.” As a proof of concept, Uber tasked one team with building a new hotel booking integration using only agent workflows. He said work that normally takes a year is completed in six months.

Sierra is also moving to expand what its platform can do beyond customer-facing agents. In April, the company launched Ghostwriter, an “agent-as-a-service” tool designed to build other agents. Users describe what they need in natural language, and Ghostwriter independently creates and deploys a specialized agent to handle it.

For Taylor, the tool underscores a broader thesis he laid out at the HumanX conference in San Francisco last month. Many enterprise software tools are barely used, he said. Employees log into Workday when they join the service and again at open enrollment, and that’s that. The future that Sierra and its investors are betting on is one in which people never need to navigate complex systems at all.