Sierra: Giving the Enterprise a Voice
The era of the enterprise agent is officially here, and Sierra is leading the way.
Over the last few years at GV, I’ve had a front-row seat to the transformation of AI from a novel experiment into a core tool, watching world-class teams build products that have become instrumental to the most complex professional workflows. It’s been amazing to watch AI move from the periphery to the very center of how the world's best professionals actually get work done.
While we have seen many incredible products designed to reshape specific industries, there is a different level of excitement when you find a standout that can tackle the one workflow and experience that is core to every single business on the planet: how a company actually interacts with its customers. Every brand, whether they sell enterprise software, healthcare services or premium leather sandals, lives or dies by its ability to create positive customer experiences.
That is exactly why we are so excited to announce that we are co-leading Sierra’s Series E financing.
For decades, interacting with a major brand has meant navigating a gauntlet of rigid chatbots and unresponsive phone trees. Bret Taylor and Clay Bavor launched Sierra two years ago with a product focused on resolving high-volume, everyday requests like returns, password resets, and billing, that traditionally frustrate customers and overwhelm support staff. And while customer service was the most straightforward entry point, their sights were always set on something much bigger: helping the best companies in the world reimagine their customer experience.
Today, Sierra is well on its way to delivering on that vision, serving companies in over 15 countries and handling a wide range of complex business outcomes from mortgage originations and proactive churn prevention.
The business metrics behind Sierra are, frankly, historic. In just over two years, they have scaled at a pace with few parallels in software history. Today, they serve 40% of the Fortune 50, and more than 30% of their customers have over $10B in annual revenue. Sierra’s agents are being adopted across all industries with customers based in 15 countries. It is remarkable to see these legacy industries move this fast, and that transformation is a direct credit to Bret and Clay.
Sierra is leading the charge because its founders have spent their lives operating within and partnering with massive organizations. Bret co-created Google Maps and led Salesforce as co-CEO, while Clay spent two decades defining how billions of us collaborate through Google. They are drawing on decades of experience in large-scale systems and product design to build the leading customer experience AI platform. And, they know exactly what it takes to build to the standards of the Global 2000, and have the credibility required to gain buy-in at that level. We’ve been floored by their velocity—crossing the $100M ARR mark in just seven quarters—helping bring the biggest and most complex organizations into the AI native future.
As I got to know Bret and Clay, what struck me most wasn't just their technical vision, but their empathy and insight on the evolving relationship between people– all of us– and AI. They started Sierra to enable what Bret calls "the end of the era of clicking buttons." Sierra’s agents interact directly with enterprise systems to get things done. Whether it’s navigating a complex mortgage origination, reactivating subscriptions, or technical troubleshooting, these agents handle action-oriented workflows seamlessly. After talking to dozens of customers who had interacted with Sierra’s agents, I was struck how much every interaction impacts a brand relationship, and how issue resolution and problem solving done right can create brand loyalty.
As we look toward what’s next, Sierra is poised to fundamentally change how the largest organizations operate. Customers using Sierra’s Agent OS have now moved far beyond customer service, optimizing entire workflows that drive revenue. This moves a brand closer to its customers by removing the organizational lag that typically gets in the way of a great experience.
We are inspired by Sierra’s ambition to build better, more human experiences with AI– what they call the “happy customer machine.” The momentum that the team has shown to transform industries and experiences is tremendous, and we are grateful to join their journey. The era of the enterprise agent is officially here, and Sierra is leading the way.
