852 Billion Valuation at Risk? OpenAI’s Strategic Shift Faces Probing Questions From Investors

TradingKey - According to the Financial Times, OpenAI’s current $852 billion valuation is facing increasing market skepticism. As the company shifts its strategic focus toward enterprise clients and competition in the AI industry intensifies, uncertainty regarding its future growth continues to rise, adding variables to its IPO plans, which could launch as early as this year.

The AI giant, valued at approximately $852 billion, is currently ramping up its expansion into the enterprise market while attempting to consolidate ChatGPT's leadership in the consumer segment, despite mounting pressure from competitor Anthropic.

Some investors are concerned that this strategic adjustment could expose OpenAI to risks, especially during the critical phase of the company's IPO preparations.

However, OpenAI’s management remains optimistic about the strategic transition. CFO Sarah Friar emphasized that the company's recently completed $122 billion funding round is the largest and most oversubscribed private financing in history, with support from more than 25 top-tier global investors serving as a strong testament to the market's validation of its strategic direction.

OpenAI Business Adjustments

OpenAI has recently targeted the higher-margin enterprise AI tools market through a series of transactions, strategic adjustments, and project trade-offs, positioning itself for a head-to-head confrontation with Anthropic.

However, some OpenAI investors point out that these strategic shifts could leave the company in a vulnerable position when facing Anthropic and a resurgent Google.

"With a flagship business like ChatGPT that has 1 billion users and an annual growth rate of 50% to 100%, why dissipate energy on the enterprise market and coding tools?" an early OpenAI investor stated bluntly. "The company is currently suffering from a serious lack of focus."

But OpenAI's management remains optimistic about the strategic pivot, given the company's track record of previous successful transformations. Just last month, CEO Sam Altman raised $122 billion from 25 top-tier investors, including SoftBank, Amazon, Nvidia, Andreessen Horowitz, and Sequoia Capital.

OpenAI CFO Sarah Friar responded, "The notion that investors do not support our strategy is untrue. Our latest funding round was the largest in history; it was not only oversubscribed but also completed in record time. The participation of numerous global investors is a testament to their confidence in our direction, business momentum, and long-term value."

In the enterprise AI market, Anthropic has emerged as an unavoidable direct competitor to OpenAI.

OpenAI executive Denise Dresser criticized Anthropic directly in her remarks, arguing that its products are limited and suffer from poor availability due to insufficient compute power, lacking structural advantages. Furthermore, as a "single-product company," Anthropic will struggle with platform-based competition as AI adoption spreads to non-technical users.

Dresser also alleged that Anthropic used accounting maneuvers to inflate its revenue, such as recording gross revenue sharing from partners as its own revenue, resulting in an annualized revenue figure overstated by approximately $8 billion.

Dresser proposed that OpenAI should shift its strategic focus entirely to the enterprise market. By integrating the model layer (Spud), platform layer (Frontier), cloud channels (AWS), and implementation services (DeployCo), the company could build a closed-loop ecosystem. This approach aims to enhance customer stickiness through multiple products and leverage compute advantages and platform breadth to establish dominance in the competition with Anthropic.

However, the market has not fully embraced this vision. On one hand, while Anthropic began with the coding tool Claude Code, it has already expanded into scenarios such as enterprise knowledge bases, customer service, and compliance audits, achieving rapid commercialization. It remains to be seen whether OpenAI’s platform strategy can successfully suppress its rival.

On the other hand, Anthropic is accelerating the buildup of its compute architecture, having reached a new agreement with Google to secure several gigawatts of next-generation TPU capacity, expected to go online by 2027. In market competition, Anthropic holds a 70% win rate among companies purchasing AI services for the first time, compared to approximately 30% for OpenAI.

OpenAI's Strategic Layout

OpenAI continues to maintain its lead in the consumer space. The pioneering launch of ChatGPT in November 2022 not only ignited the AI chatbot market and drove the company's transition into a for-profit enterprise, but also prompted its commitment of hundreds of billions of dollars toward compute infrastructure.

However, Sam Altman issued a "red alert" late last year, urging employees to focus on core business operations. Last month, Fidji Simo, the head of applications and former CEO of Instacart who is currently on medical leave, also called on the team to stop "irrelevant side projects."

Yet two weeks later, OpenAI still acquired the tech talk show TBPN for "hundreds of millions of dollars." In response, an OpenAI executive explained that the show does not count as a "side quest" because it will not consume the company's computing resources.

In addition, a $1 billion collaborative project originally planned by Disney has been terminated because OpenAI shut down the video generation tool Sora. Meanwhile, Microsoft stated that if OpenAI's newly reached $5 billion partnership with Amazon violates their exclusive cloud services agreement, it will take legal action.

Adjustments have also emerged in OpenAI's $500 billion "Stargate" data center plan announced at the White House. Projects originally planned for a $30 billion data center investment in the UK and the expansion of the Abilene, Texas site have both been canceled, and a $100 billion partnership with Nvidia has been significantly scaled back.

Nonetheless, OpenAI is still expanding in some sectors, planning to nearly double its headcount to 8,000 from current levels by the end of this year, while expecting the revenue share from enterprise customers to rise from approximately 40% now to 50%. This Monday, OpenAI announced it had signed a lease to establish a new permanent office in London next year, with plans to set up its largest research hub outside the U.S. there.

OpenAI signed several major compute procurement agreements last year, which represents a significant advantage over Anthropic. Last week, the company disclosed to investors that it currently possesses 8 gigawatts of computing power, a scale Anthropic will not reach until late 2027; OpenAI aims to increase its compute capacity to 30 gigawatts by the end of 2030.

Anthropic’s Rise Reshapes the AI Competitive Landscape

Anthropic's explosive growth is one of the core external factors driving OpenAI's strategic pivot. The AI company, centered on the Claude model, saw its annualized revenue soar from $9 billion at the end of 2025 to $30 billion by the end of March 2026, driven primarily by robust demand from enterprise clients for its coding tools. This revenue scale has surpassed OpenAI's annualized revenue record of $25 billion set in February this year (though direct comparisons may be limited due to different accounting methodologies used by the two companies).

Secondary market trading data indicates that investor enthusiasm for Anthropic has overtaken OpenAI, with Anthropic's valuation trading at a premium to OpenAI for the first time.

This news has also continued to weigh on valuation confidence for OpenAI in the primary market, forcing the company to prove its growth resilience through tangible business progress and data.

In response to external skepticism, OpenAI Chief Revenue Officer Denise and her team are attempting to shift market perception. Denise stated that since entering the second quarter, the team has engaged in deep discussions with heads of leading enterprises, high-potential startups, and top-tier investment firms. These parties have shown significant anticipation for OpenAI's projects in development and are seeking a deeper understanding of the company's technology and business roadmap to plan their own AI strategies with greater confidence.

Denise joined OpenAI in December 2025 after a tenure of over 14 years at Slack, where she also served as CEO and spearheaded its integration with Salesforce. With extensive experience in enterprise-level revenue strategy, she now oversees OpenAI's global enterprise and customer revenue operations.

Focusing on the enterprise AI market, where the willingness to pay is strongest, recent third-party data shows OpenAI's market share has dropped to 35.2%, with the gap between it and Anthropic narrowing to just 4.6 percentage points. Based on this trend, Anthropic is poised to overtake OpenAI within the next two months.

However, Denise disputes this assessment, arguing that the enterprise AI market is entering a mature phase where raw model capabilities are no longer the sole criterion for selection. Instead, clients prioritize the fit between AI systems and their specific business needs, including compatibility with business workflows, knowledge systems, control mechanisms, and daily operations, as well as the ability for efficient deployment, continuous optimization, and earning long-term trust.