Study: AI success is now a CEO survival test

Welcome back. Today’s issue is about the enterprise AI gap. Everyone can access powerful models now, but few companies have figured out how to turn them into reliable outcomes. That’s why process intelligence matters so much, and why deploying agents without understanding how work actually happens can scale up chaos. OpenAI and Anthropic are pushing beyond just model contests into Wall Street-backed deployment machines, racing to own enterprise relationships before their respective IPOs. And CEOs are feeling the squeeze, with boards demanding measurable AI results while legal, trust, and observability risks slow rollouts. One of AI’s biggest tests of 2026 remains enterprise execution. Jason Hiner

IN TODAY’S NEWSLETTER

1. Study: AI success is now a CEO survival test

2. How deployment became AI’s new battleground

3. Why AI fails without process intelligence

LEADERSHIP

Report: AI pressure is rattling CEOs

AI is making stakeholders excited and CEOs nervous. 

A recent global study of 900 CEOs, conducted by Harris Poll and AI firm Dataiku, finds that 81% of those surveyed fear that failing AI deployments could cost them their jobs this year. Despite the high stakes of getting AI right, many still worry about what happens when it gets things wrong: 34% said they wouldn’t allow AI to make decisions without human approval. 

The pressure on these executives is coming in from all sides: 

  • Around 62% of CEOs report that their boards are actively pressuring them to deliver measurable AI-driven outcomes.

  • Meanwhile, 75% reported that they believe a fellow CEO will be ousted as a result of a bungled AI rollout. 

  • CEOs are largely concerned about competitors getting ahead: 56% admit their competitors have stronger AI strategies than they do. 

The problem can be summed up by a phrase that’s been floating around since last year: Capability overhang. There is no question that these models are capable of incredible things, but actually deploying them is another ballgame altogether. 

And despite the pressure, there are still major trust issues around the risks that this tech presents. 79% worry about the legal risks and ramifications of using the technology, and 57% worry about the inability to trace an AI output back to its source. Concerns about these risks are causing holdups: 51% reported delaying their rollouts due to regulatory issues. 

“Every enterprise now has access to powerful AI,” Florian Douetteau, CEO and co-founder of Dataiku, said in a statement. “The differentiator is whether they can turn that power into reliable business decisions. That is the cognitive dissonance happening in the C-suite right now.”

As CEOs begin to crack under the pressure to deliver results, they face the same looming unease about the tech that everyone is grappling with. Models are growing more powerful by the day, promising to upend every industry. Keeping up with the shifting tide of AI is becoming untenable. With the narrative growing that AI will permanently alter the way we work, live and think, the question may be whether we should slow down and consider what we should allow this tech to alter. As one CEO expressed it at the HumanX event: "Slow down to speed up."

Nat Rubio-Licht

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MARKETS

 AI showdown shifts from models to enterprise

Anthropic and OpenAI are in a battle for the hearts and minds of enterprises. Now, both companies have enlisted reinforcements. 

The AI darlings have separately struck multibillion-dollar deals with major Wall Street firms that aim to accelerate AI adoption in businesses. The deals signify the heated fight between OpenAI and Anthropic to cement themselves as the vendor of choice for enterprise as these firms race towards profitability. 

News of both deals broke on Monday within minutes of one another: 

  • Anthropic inked a partnership with Blackstone, Hellman & Friedman, and Goldman Sachs to form a new “AI-native enterprise services firm” with the goal of integrating Claude into companies’ core operations. The firm is a standalone entity utilizing Anthropic’s engineering. It expands on a $200 billion deal these firms struck in April and is worth around $1.5 billion, according to The Wall Street Journal

  • OpenAI, meanwhile, raised more than $4 billion from a host of investors, including TPG, Brookfield, and Bain Capital, for an entity focused on helping businesses deploy AI into their operations, according to Bloomberg. The joint venture, which is aptly named The Deployment Company, is reportedly valued at $10 billion. 

The rivalry between OpenAI and Anthropic has never been more heated. The companies have been leapfrogging each other's models in capabilities for months and pushing new models and upgrades for Codex and Claude Code that aim to capture developer and enterprise attention. 

The flurry of improvements also come ahead of each of these firms’ expected IPOs, with both companies anticipating going public in late 2026. With so many eyes on them and dollars flowing towards them, lining up contracts for businesses to use their tech is critical.

Though Anthropic has built its reputation around being an enterprise favorite, OpenAI has made a hard pivot toward the enterprise over the past several months. The company pruned consumer projects, such as Sora, to dedicate more resources and compute to its core models, and has been on a tear releasing new updates for Codex, including turning the coding tool into an everyday work agent. Additionally, its partnership with AWS is building momentum across the enterprise, startups, and government entities. Still, the arms race between these two firms is far from over, and the winner is still unclear. The competition is great for organizations looking to get the best deal on the most advanced AI solutions.

Nat Rubio-Licht

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BIG TECH

Why AI fails without process intelligence

In this episode of The Deep View Conversations, we sit down with Alex Rinke, co-founder and co-CEO of Celonis, to unpack one of the most overlooked truths in enterprise AI.

Rinke and his co-founders started Celonis 15 years ago in Munich with just $15,000. What followed was a grind, including thousands of handwritten letters to land early customers, and a steady evolution from process simulation to what is now known as process intelligence.

Today, Celonis works with roughly half of the world’s 200 largest companies. Its platform acts like an MRI for the enterprise, creating a digital twin of how work actually happens across fragmented systems.

Rinke’s core argument is simple and provocative: there is no enterprise AI without process intelligence. Companies that deploy agents without understanding their underlying processes risk automating inefficiency at scale.

We also cover:

  • How Celonis re-engineered itself for the AI era

  • What the co-CEO model works like in practice and why it can be a competitive advantage

  • How hiring is changing inside AI-native companies

  • The tools Rinke uses to run his own workflow

If you want to understand where AI actually delivers results inside large organizations, don't sleep on this conversation.

Watch now and subscribe for more conversations at the frontier of AI.

Jason Hiner, Editor-in-Chief

LINKS

  • Google WebMCP: “provide a standard way for exposing structured tools,” early preview

  • Shared knowledge: Zapier's personal AI assistant is available in beta via a waitlist 

  • OpenClaw 2026.5.3: New release includes file transfer for paired nodes and more

  • ChatPlayground AI: Tool to see answers from multiple AI models in same place

GAMES

Which image is real?

Login or Subscribe to participate in polls.

POLL RESULTS

Do you, or would you, let Codex or another agent handle your day-to-day work tasks?

Yes, I already do (13%)
Yes, I’m considering it (21%)
I’m not sure (31%)
No, I would not (25%)
Other (10%)

The Deep View is written by Nat Rubio-Licht, Sabrina Ortiz, Jason Hiner, Faris Kojok and The Deep View crew. Please reply with any feedback.

Thanks for reading today’s edition of The Deep View! We’ll see you in the next one.

“The waves are more organic in this image.”

“The sea wall is too random for AI to think of. If you asked AI to recreate that image, it would put rocks there or remove it entirely. ”


“There is more variability in this image, especially the water.”

“Apparently, AI can’t do focus optics well. With AI, everything is in focus and sharp. Real photos not so much.”

“Shadows in [this image] didn't look real.”


“Showed too much [clarity] where it should have been more on the blurry side.”

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