Ex-Salesforce CEO Bret Taylor’s AI venture raises $350M at $10B valuation

In just 18 months, Sierra has onboarded hundreds of enterprise clients—including SoFi, Ramp, and Brex—by leveraging its founders’ deep industry expertise to deliver AI-powered customer service agents tailored for large-scale business needs

Sierra, an enterprise-focused AI startup co-founded by former Salesforce co-CEO Bret Taylor, has raised $350 million in a new funding round, pushing its valuation to a staggering $10 billion. The round was led by Greenoaks Capital, one of the company’s early backers, and confirmed in a blog post by Sierra on Thursday.

The latest investment brings Sierra’s total funding to $635 million since its inception in early 2024. Previous rounds included a $110 million raise in February 2024, led by Sequoia and Benchmark, and a $175 million round in October, also spearheaded by Greenoaks. Other major investors include ICONIQ and Thrive Capital.

Enterprise adoption and founders' track record fuel growth

Sierra specializes in building AI-powered customer service agents tailored for enterprise use. In just 18 months, the startup has onboarded hundreds of clients, including financial tech firms SoFi, Ramp, and Brex. The company’s rapid adoption is credited in part to the deep industry expertise of its founders, Bret Taylor and Clay Bavor.

Taylor, known for co-founding productivity platform Quip and later serving as Salesforce’s co-CEO, brings a rich background in enterprise software. Bavor, a former Google executive, led development for products like Gmail and Google Drive. The two met while working at Google and have remained collaborators since.

Their combined experience in building scalable, consumer-grade technology for business environments appears to be resonating with investors and customers alike, as demand for enterprise AI solutions continues to surge.

Talent development in a competitive market

In addition to its funding milestone, Sierra also announced the second year of its APX program—an initiative designed to attract recent computer science graduates. Modeled after Google’s early-career engineering tracks, the program gives new hires hands-on experience in both technical development and product management.

Taylor described the initiative as offering “an irresponsible amount of responsibility,” aiming to replicate the entrepreneurial freedom he and Bavor once experienced at Google. The move comes amid widespread tech layoffs and hiring slowdowns, positioning Sierra as a rare beacon of opportunity in a cautious job market.