Sierra —

At Sierra, we envision a future where every business, regardless of size, can deliver deeply human and personalized customer experiences through intelligent AI agents. Our mission is to democratize access to sophisticated conversational AI that not only understands and responds but takes meaningful actions within business systems, transforming the way companies engage with their customers.

We are building a secure, compliant platform that integrates seamlessly with enterprise workflows and data, empowering organizations to scale customer interactions thoughtfully and efficiently. By harnessing advanced AI technologies and a principled approach to data privacy, we are shaping the next generation of customer service, where AI agents act as trusted digital partners aligned with brand values.

Driven by deep expertise and bold vision, Sierra is committed to enabling businesses to unlock new levels of operational excellence and customer satisfaction, creating a future where technology amplifies human potential in every interaction.

We've been tracking Sierra since their public debut, and honestly, the hype feels justified. When you've got Brett Taylor (former Salesforce co-CEO) and Clay Bavor (Google's former AR/VR chief) building AI agents together, you pay attention. But beyond the star power, Sierra's approach to conversational AI genuinely caught our eye.

What Makes It Different

Most AI chatbots are glorified FAQ machines. Sierra's agents actually do things—they update your CRM, manage orders, and handle real business processes while staying perfectly on-brand. We tested their platform with a few enterprise contacts, and the difference is striking. These aren't just smarter responses; they're functional extensions of your team.

The outcome-based pricing model is clever too. You only pay when the AI actually resolves a customer issue, which aligns incentives nicely. Though at $150K+ annually plus setup fees, this isn't exactly small business territory.

The Enterprise Sweet Spot

Sierra shines brightest with companies that have predictable support spikes—think WeightWatchers during New Year's resolution season or Sonos during the holidays. We love how their AgentOS integrates with existing business systems rather than creating another silo. The compliance and security features feel enterprise-ready from day one, not bolted on later.

The Experience Manager interface impressed us too. Marketing teams can actually shape how these agents sound and behave without needing a computer science degree.

Room for Growth

We did hear consistent feedback about the learning curve being steeper than expected. Some users found customization options limited for truly unique workflows, and performance occasionally hiccups during complex, multi-turn conversations. For a platform targeting enterprise customers, these friction points matter.

That said, going from zero to $20 million ARR in under two years—and landing a $10 billion valuation—suggests they're solving real problems for real companies. We're curious to see how they scale beyond their current enterprise sweet spot.