Why Apple CEO Tim Cook’s AI struggles serve as a warning for C-suite leaders

In a new Fortune article, my colleague Geoff Colvin highlights the dilemma facing Apple CEO Tim Cook. Cook, who became CEO in 2011 after serving as chief operating officer, succeeded Steve Jobs. As COO, he was responsible for the company’s worldwide sales and operations.

“It seems impossible that Tim Cook’s legacy as Apple’s spectacularly successful CEO could be in jeopardy,” Colvin writes. “But in recent months, and especially in recent days, the impossible has become at least conceivable.”

Some are questioning whether Apple is losing momentum under Cook’s leadership, as its stock has declined about 16% in 2025, significantly underperforming both the broader market and tech peers like Microsoft and Meta. Analysts and technology commentators have criticized Apple for “falling behind” competitors in AI. Recent efforts, such as the Apple Intelligence rollout, are seen as underwhelming. And Apple’s top executive in charge of AI models is leaving for Meta. 

Yet, under Cook, Apple became staggeringly successful. When Steve Jobs recommended Cook as CEO, Apple’s valuation was about $300 billion. Today, it stands at $3.2 trillion—an extraordinary compound annual growth rate of 18.4% over 14 years. In fact, Colvin notes that Cook has generated significantly more shareholder value than Jobs did during his tenure.

The widespread rise of AI presents a challenge that Apple may not have been fully prepared. “For a company of Apple’s scale and stature, lagging behind its major competitors on AI is like lagging behind the competition on the internet in 2000,” Colvin writes. “AI is a general-purpose technology, and those things don’t come along very often. The internet was one. So were digital computing and electricity. They change the world, and they revolutionize the business landscape for every company.”

As Colvin puts it: “With that in mind, it becomes clear how Tim Cook could be one of the all-time greatest CEOs from 2011 to now, yet might not be optimal for the AI era.” You can read more of Colvin’s assessment, along with discussions with experts, here.

You don’t have to be a trillion-dollar company to feel the pressure for AI to redefine your leadership. In this new age of AI, product innovation, agility, and moving quickly—but wisely—are critical to remaining competitive. Baba Prasad, professor of the practice of leadership at Brown University, writes in a recent opinion piece that the very nature of leadership is being transformed by AI.

Prasad writes: “In the AI-driven world, visionary agility enables leaders to interpret new information meaningfully, challenge what must be challenged, and steward resources and technologies in alignment with broader human purposes. These three functions—interpreter, challenger, and steward—are the critical roles of agile leadership in an AI-driven world.”

Sheryl Estrada
sheryl.estrada@fortune.com

Leaderboard

Mukul Mehta was promoted to CFO of pharmaceutical company Novartis (ECN), effective March 16, 2026. Mukul succeeds Harry Kirsch, who has served as CFO since 2013, and will retire from Novartis after a 22-year career with the company. Harry will continue in his role as CFO until March 15, 2026. Mukul brings over 20 years of experience at Novartis. He was recently appointed to the role of head of BPA, Digital Finance and Tax, where he will continue until March of next year. His career includes serving as CFO International for three years, ad-interim President International, CFO Pharmaceuticals business unit, CFO Novartis Business Services, CFO Pharmaceuticals Europe business, and Country CFO of France, Poland, and Norway.

Brandy Richardson was appointed CFO of multi-brand luxury retailer Saks Global, effective Aug. 18. Richardson succeeds Interim CFO Mark Weinsten, who joined Saks Global to lead the company’s finance organization through the initial stages of its transformation following its acquisition of Neiman Marcus Group (NMG) in December 2024. With nearly 25 years of experience, Richardson joins Saks Global from Tailored Brands, Inc., where she has served as EVP and CFO. Richardson spent the majority of her career at NMG, where she held several finance leadership roles of increasing responsibility over her 15-year tenure.

Big Deal

In the first half of 2025, funding for generative AI companies has already surpassed 2024’s full-year record. This surge, driven primarily by OpenAI’s $40 billion round and Scale AI’s $14.8 billion minority stake sale to Meta, highlights intensifying competition for resources and talent among leading frontier model providers, according to an S&P Global Market Intelligence analysis. 

Investors allocated about $70 billion to generative AI startups in the first six months of this year, up from $58.7 billion in all of 2024. Funding for AI companies without frontier models also hit a quarterly record, with $2.4 billion raised in Q2, exceeding the previous high set in late 2024.

S&P Global Market Intelligence’s 451 Research projects that AI coding revenue will see the fastest growth through 2029, with a compound annual growth rate of 53.4%.

Going deeper

“JPMorgan’s plan to charge for data could ‘cripple’ crypto and fintech startups, execs warn” is a new Fortune report by Luisa Beltran.

From the report: “When JPMorgan Chase told fintechs last month that it planned to charge them for accessing its customer banking account data, it sent shockwaves through corners of the financial industry. According to four industry executives, the move is a blow to the fintech sector and could prove devastating to early-stage startups, including those in the crypto industry. Analysts, however, think mature fintechs like PayPal and Block will likely not feel much consequence from this fee change.”

Overheard

“The businesses that win in the long term are the ones that innovate. That create new products. That reimagine how things should work, and find radical breakthroughs that impress their customers in new ways.”

—Alexandra Ebert, chief AI and data democratization officer at Mostly AI, writes in a Fortune opinion piece.