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OpenAI Chair's Sierra may hit $100M ARR, valued at $10B in 2 years

The “Shopify of Energy” grows $1M to $5.5M ARR in Just 8 Months

John Tian's avatar
John Tian
Sep 03, 2025
∙ Paid

Anthropic has officially announced its $13 billion Series F funding round, co-led by Iconiq, Fidelity, and Lightspeed, bringing its post-money valuation to $183 billion.

The disclosed numbers are indeed impressive:

RRR has reached $5 billion, up from just $1 billion at the beginning of this year; the company now serves over 300,000 enterprise customers, with the number of large clients spending more than $100,000 annually growing 7x over the past year.

Additionally, Claude Code is showing explosive momentum—its RRR has already surpassed $500 million, with usage increasing tenfold in just three months.

Anthropic CFO Krishna Rao said they are witnessing exponential growth in demand across their customer base.

Sierra reached a $10B valuation in 2 years

Meanwhile, Sierra, the AI customer service product co-founded by OpenAI Chairman Bret Taylor, reportedly closed a new financing round after last October’s $175 million raise at a $4.5 billion valuation.

This new round raised $350 million, instantly pushing Sierra’s valuation to $10 billion, with Greenoaks Capital—the lead investor from the previous round—said to be leading again.

OpenAI Chair's AI startup Sierra at $20M ARR in one year

OpenAI Chair's AI startup Sierra at $20M ARR in one year

John Tian
·
October 31, 2024
Read full story

If confirmed, that would mean Sierra reached a $10 billion valuation in just two years, likely making it the first AI customer agent to do so.

Sierra’s ARR is around $100 million, which puts its valuation-to-revenue multiple at 100x—arguably excessive.

After all, another AI customer agent Crescendo has already surpassed $100 million ARR as well, yet its valuation stands at only $500 million, while raised $50 million in October 2024, led by General Catalyst.

0-$90M ARR in 15 months, AI is Revolutionizing CX business

0-$90M ARR in 15 months, AI is Revolutionizing CX business

John Tian
·
April 29, 2025
Read full story

In June, Sierra announced that it had several hundred customers, primarily large enterprises, with 15% of them generating over $10 billion in annual revenue and 50% generating over $1 billion.

The “Shopify of Energy” grows $1M to $5.5M ARR in Just 8 Months

Most of renewable energy installations are carried out by small and medium-sized installers, yet these businesses lack sophisticated tools for financing, sales, and customer management.

Hence, the opportunity for the AI-powered "Shopify of Energy" arises: an operating system that connects every stakeholder in the transition: installers, homeowners, manufacturers, energy suppliers, and investors.

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