Investor enthusiasm surrounding Sierra, the artificial intelligence venture founded by former Salesforce co-chief executive Bret Taylor, has reached remarkable levels, with the company’s most recent financing round underscoring both confidence in its vision and momentum in the market. On Thursday, Sierra announced it had successfully secured an impressive $350 million in fresh capital. The round was spearheaded by existing backer Greenoaks Capital, a firm that has consistently demonstrated its conviction in Sierra’s long-term potential. This latest infusion of funds now places the company’s valuation at a staggering $10 billion, a milestone publicly confirmed in an official blog post that corroborated an earlier exclusive first disclosed by Axios earlier in the week.
Sierra, though relatively young as a business entity, was established in early 2024 through the collaboration of Bret Taylor and Clay Bavor, the latter a seasoned Google veteran. Despite being less than two years into operations, the startup asserts that it has already recruited hundreds of enterprise clients to its platform. Among these are high-profile names such as SoFi, Ramp, and Brex, each of which relies on Sierra’s AI-driven customer service agents to improve efficiency, scalability, and customer engagement. Such early adoption, particularly from leading financial services and technology companies, provides a compelling demonstration of Sierra’s promise in transforming the landscape of enterprise-level customer support.
The company’s fundraising trajectory further illustrates the intensity of investor belief in its mission. In addition to the newly closed $350 million round, Sierra has now amassed a cumulative total of $635 million in funding. Earlier rounds include a $110 million raise finalized in February of last year, led by renowned investment firms Sequoia Capital and Benchmark, as well as a separate $175 million financing that closed in October under the leadership of Greenoaks once again. Complementing these heavyweight investors, other participants such as ICONIQ Capital and Thrive Capital have also joined the roster, further reinforcing Sierra’s credibility and signaling widespread investor appetite for AI-powered solutions at the enterprise scale.
Part of Sierra’s appeal stems from the unique expertise of its founding team. Both Taylor and Bavor bring decades of frontline experience in building and scaling groundbreaking technologies dedicated to communication, productivity, and customer experience. Taylor’s career trajectory is especially impressive: he dedicated nearly a decade to Salesforce, during which time he co-led the company as co-CEO, while also previously founding the collaborative productivity platform Quip. That startup was later acquired by Salesforce in 2016 for approximately $750 million. Bavor, on the other hand, spent years at Google overseeing essential consumer products such as Gmail and Google Drive that have become ubiquitous tools in both professional and personal digital life.
The history of collaboration between Taylor and Bavor can be traced back to their tenure at Google, where their professional relationship first took root. Taylor, prior to his leadership position at Salesforce, had served as Facebook’s Chief Technology Officer and earned recognition for his significant role in launching Google Maps, one of the company’s most transformative and widely adopted products. Beyond those contributions, Taylor’s leadership was also on display when he chaired the Twitter board during Elon Musk’s tumultuous acquisition of the social media giant, a role that placed him directly in one of Silicon Valley’s most closely scrutinized corporate dramas.
Even as Sierra continues to secure funding and expand its product footprint, it is simultaneously investing heavily in talent development and workforce opportunities. Earlier this week, Taylor revealed that Sierra would be entering the second year of its so-called APX fellowship initiative, a program designed explicitly for recent university graduates specializing in technical disciplines such as computer science. Modeled closely after the rotational program at Google that originally launched both Taylor’s and Bavor’s own careers nearly two decades ago, APX offers graduates an intensive, accelerated learning environment.
In contrast to the current climate, where the technology job market is increasingly characterized by caution, layoffs, and reevaluations of traditional hiring models due to the fast-moving influence of AI, Sierra’s hiring push is particularly noteworthy. The APX program emphasizes hands-on experience in multiple facets of Sierra’s operations—most prominently within agent engineering and product management. By giving participants the chance to directly contribute to the building, design, and deployment of cutting-edge AI technologies, Sierra positions them not as passive learners but as active leaders in shaping the company’s offerings. Taylor himself has described these roles as carrying what he terms “an irresponsible amount of responsibility,” a phrase that underscores the autonomy and accountability entrusted to new graduates. This approach echoes the environment he and Bavor once experienced at Google, where they gained freedom to create and ship products that would eventually influence millions of users. In the same spirit, Sierra intends for APX participants to be integrally involved in the launch of multiple major products within their very first year, ensuring that graduates emerge not only with significant technical proficiency but also with the rare confidence of having had ownership over real-world, high-impact initiatives.
In sum, Sierra’s recent $350 million funding achievement and accompanying $10 billion valuation signify more than just investor faith in a promising startup. They represent a broader acknowledgment that Sierra, under the stewardship of Taylor and Bavor, is poised to become a central player in redefining customer service through the intelligent automation of AI agents. By coupling deep technical expertise with an aggressive yet thoughtful strategy for talent cultivation, the company is both scaling rapidly and laying the groundwork to ensure its technologies and workforce remain at the forefront of an AI-first future.
Sourse: https://techcrunch.com/2025/09/04/bret-taylors-sierra-raises-350m-at-a-10b-valuation/
