Sierra

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Sierra is an enterprise conversational AI platform that builds branded, autonomous customer-experience agents. Founded in 2023 by Bret Taylor (former co-CEO of Salesforce and current chair of OpenAI's board) and Clay Bavor, who previously led Google Labs and Google's VR efforts, the San Francisco company has become one of the fastest-growing names in enterprise software, crossing $100M in ARR in under two years (reportedly $150M+ by early 2026) and counting more than 40% of the Fortune 50 among its customers, including Prudential, Cigna, Blue Cross Blue Shield, and Rocket Mortgage. The platform, branded Agent OS, lets companies build, test, deploy, and continuously improve AI agents that operate across chat, voice, email, SMS, and WhatsApp in 30+ languages. Its model-agnostic 'constellation' architecture orchestrates multiple LLMs (OpenAI, Anthropic, Google, Meta) per task. Agent OS 2.0 spans roughly eight products, including Agent Studio for configuration (with no-code Journeys, Workspaces, and an Integration Library), an Agent Data Platform for persistent memory and context, and Live Assist for human escalation. As the first Level 1 PCI-compliant conversational AI platform, Sierra's agents can complete end-to-end commercial transactions (collections, renewals, and purchases), not just resolve support tickets. In March 2026 Sierra launched Ghostwriter, an 'agent that builds agents': a business user describes what they need in plain English, or uploads SOPs, transcripts, and recordings, and Ghostwriter generates a production-ready agent, lowering the barrier to deployment for non-technical teams. Sierra prices on outcomes, charging only when an agent resolves an issue, saves a cancellation, or completes an upsell. It has raised over $1.58 billion total, most recently a $950 million Series E (May 2026) led by Tiger Global and GV at a $15.8 billion valuation.