Sierra, which builds enterprise-focused customer service agents, has secured a fresh $350 million in funding led by Greenoaks Capital, valuing it at $10 billion. The latest raise brings Sierra’s total funding to $635 million.
Previous rounds included $110 million led by Sequoia and Benchmark in February 2024 and $175 million from Greenoaks in October of the same year. With participation from ICONIQ and Thrive Capital, Sierra has built an enviable investor lineup.
Founders with an impressive track record
Sierra was founded in 2024 by former Salesforce co-CEO Bret Taylor and ex-Google executive Clay Bavor.
Taylor and Bavor are no strangers to building transformative products. Taylor’s resume spans co-leading Salesforce, founding productivity platform Quip (acquired by Salesforce for $750 million), and playing an important role in developing Google Maps. He also served as Facebook’s CTO and chaired Twitter’s board during Elon Musk’s takeover.
Bavor, meanwhile, spent years at Google shaping Gmail and Google Drive, two of the company’s most widely used products. Their shared history dates back to Google, where they first worked together. That long-standing partnership now fuels Sierra’s trajectory.
Reimagines customer service at scale
Customer service has historically been a pain point for enterprises—expensive, labour-intensive, and often frustrating for end-users. Sierra’s technology is designed to address these challenges head-on by enabling companies to deploy responsive, context-aware service agents. By focusing squarely on enterprise-grade solutions, Sierra differentiates itself from consumer-facing tools and positions itself as a partner for companies needing reliable, scalable support infrastructure.
The AI company has already built a roster of clients, including SoFi, Ramp, and Brex. In just 18 months, it has claimed hundreds of enterprise customers, an achievement that signals strong product-market fit. By focusing on customer service automation, Sierra is tapping into a universal business need: scaling support without sacrificing quality.
The APX program: Betting on fresh talent
In addition to scaling its technology, Sierra is also investing in the next generation of builders. Earlier this week, Taylor announced the second year of Sierra’s APX program, a rotational opportunity for recent computer science graduates. Modelled after the program that launched Taylor’s and Bavor’s own careers at Google, APX gives new hires significant responsibility early on.
Participants rotate across agent engineering and product management, contributing to multiple product launches within their first year. Taylor describes the approach as giving graduates an irresponsible amount of responsibility, aimed at cultivating entrepreneurial thinkers rather than narrowly specialised engineers.
A bright spot in a tough job market
The launch of APX also stands out against the backdrop of a challenging job market in the tech industry. While many companies are downsizing or freezing hiring, Sierra is creating new pathways for graduates to enter the field. For young talent, the program offers both hands-on experience and the opportunity to contribute to high-impact products, a rarity at such an early stage in their career.
What’s next for Sierra?
With $350 million in new funding and a $10 billion valuation, Sierra is now one of the most closely watched startups in the enterprise technology sector. Its challenge will be to maintain its rapid pace of customer adoption while refining the sophistication of its service agents.
Given the founders’ track records and the calibre of backers lining up, Sierra is well-positioned to shape how companies think about customer service in the coming decade.
