OpenAI Chairman’s Sierra AI Raises Mega Round at $16B Valuation

Sierra AI, an enterprise conversational AI startup co-founded by OpenAI Chairman Bret Taylor, has raised a funding round valuing the company at nearly $16 billion, CNBC reported.

The deal ranks among the largest funding rounds for an AI-adjacent startup in recent memory, according to CNBC.

Taylor, who serves as chairman of OpenAI’s board of directors, co-founded Sierra in 2023 alongside former Google executive Clay Bavor. The company builds AI agents designed to handle customer interactions for large enterprises.

Sierra has attracted enterprise customers seeking to deploy conversational AI agents across customer service and sales operations, according to CNBC.

Taylor’s dual role as OpenAI chairman and Sierra chief executive has drawn scrutiny over potential conflicts of interest, according to CNBC, though the two companies operate in distinct market segments. OpenAI focuses primarily on foundational AI models and consumer products, while Sierra targets enterprise customer experience applications.