As Apple gears up to anoint John Ternus the new company CEO in September (while current leader Tim Cook takes a seat on the board) the company appears to be firing on all cylinders ahead of the leadership transition. 

What’s going well

Just look at the evidence: 

• Apple is building market share across its entire product range; even memory-driven price inflation doesn’t seem to have dampened demand for its hardware yet.
• While Apple had to raise prices, the company’s MacBook Neo remains seriously popular. It’s sitting atop Amazon’s US best-selling chart, which currently includes six Macs in the top 10. The Neo has topped this chart since its introduction.
• Apple’s iPhone 17 series continues to sell well, with recent market data showing sustained growth. Both Counterpoint and IDC tell us that iPhone shipments continue to increase, even as other vendor shipments slide.
• IDC analyst Francisco Jeronimo recently estimated that Apple’s upcoming foldable iPhone Ultra could grab 29.4% of global folding smartphone sales this year, rising to 34.9% in 2027.
• The company’s new 27 series of operating systems is attracting a great response as beta testers report that it is already solid, stable, and performing well.
• The AI narrative has really changed, with analysts no longer quite so starry-eyed at the prospects for the big frontier AI firms. Apple’s edge-AI-enabling approach is winning converts.

What’s coming up

The company’s newly-filed lawsuit against OpenAI may or may not succeed, but it will certainly help consolidate recognition of the importance of Apple’s designs and intellectual property in whatever hardware emerges from the AI firm. It also means both Apple and OpenAI are already competing in hardware, even though neither company yet offers anything that directly challenges the other. 

Apple has just set out its stall to brand-loyal fans in a big way and did so before OpenAI gets to woo the same set of customers with a wriggle of its Jony Ive-tinged talisman.

The stage is set for intense competition between the two. Though some say Apple’s needs to improve employee retention, if it does find proof of efforts to use recruitment to engage in industrial espionage, it’ll be easier to represent its own products as being the OG for new hardware. 

If nothing else, it means consumers will forever be asking, “If OpenAI’s designers are so good, why did it need to poach them from Apple?” Doubt is a weapon.

Managing perception

It doesn’t matter how the case goes, because there fight is already affecting consumer psychology. It also means that as Ternus prepares to take his seat atop the rainbow-colored Apple throne, we can already size him up. “A man is measured by his enemies,” Joe Abercrombie wrote in “The Trouble With Peace.”

Given the proximity of the leadership transition, it’s highly probable that Ternus signed-off on the litigation; in doing so he — and Apple — tell us to expect more of the same. 

Apple has, rightly or wrongly, decided that OpenAI will become its new existential bugbear, following in the footsteps of Microsoft Windows, Real Networks, Adobe Flash, Android, and Samsung, all of whom have been useful foils against which Apple has been able to build and maintain its identity.

Looking at that list, you’d be tempted to believe that nothing much is new. Apple has often defined itself by the enemies it sometimes keeps. What has been will be again, which in this case means even as OpenAI attempts to carve out an identity as a hardware manufacturer delivering solutions to compete with Apple and Google, Ternus’ team’s looks to drive a consensus-shaped wedge into the pro-LLM propaganda. 

That blow comes as Apple finally gets its act together around AI, and as the company prepares for a future in which the world’s most-used wearable device also becomes the wearable way to woo Siri AI.

My kingdom come

Rising market share, powerful solutions, an increasingly recognized and respected approach to AI, and an ideological crusade — these details constitute Apple’s place today and are Tim Cook’s coronation gift to Ternus. He’s passing along a strong and hyper-profitable baton that screams of timeliness and relevance even as the company gets set, ready, to go with a year or two of new product designs, new product families, and a 20^thanniversary iPhone.

This is Apple’s party. OpenAI’s name didn’t make the list. 

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Healthy software companies typically don’t suddenly eliminate one-fifth of their workforce, but monday.com is doing just that as it bets on flatter teams, AI agents, and customer implementation expertise as the winning combination in the AI era.

Monday.com co-founder and co-CEO Eran Zinman today announced the “very difficult decision” to reduce the AI work platform company’s global workforce by about 20%, or 620 people.

The move has nothing to do with increasing margins or replacing humans with AI, he insisted in his post on LinkedIn; rather, it’s a calculated decision to trim down and hone the company’s focus as AI becomes integral to day-to-day workflows.

“This is not a distress signal; it is a deliberate reset, disclosed with its price attached,” said Sanchit Vir Gogia, chief analyst at Greyhound Research. “The industry has quietly swapped the meaning of productivity, and this filing is the clearest exhibit yet.”

A ‘significant opportunity’ in technology

In a SEC filing this week, monday.com said its restructuring plan reflects the “ongoing transformation of its product, marketing, and go-to-market strategy.” The move is intended to support a “leaner, more focused operating model” as the company continues to invest in its AI-driven strategy.

Zinman noted in his post that the company has shifted to “doing the work with AI and not just managing it,” and is focused on building environments where “people and AI agents [work] together in one workspace.”

In recent months, monday.com has evolved its products, strategy, and the way it serves its customers, and Zinman contended that “the organization we built for our previous chapter is not the organization that fits the new AI era.” Monday.com needs to “execute more decisively,” take on new challenges, and quickly respond to market changes, he said.

“We have never seen such a significant opportunity in software, driven by such exciting technology,” Zinman noted. He emphasized that the reduction is not to replace people with AI, nor to improve margins; the “vast majority” of savings will be reinvested into talent, products, and AI.

The restructuring will result in a “flatter organization” with fewer management layers and smaller, more autonomous teams, and monday.com also has a new go-to-market model, Zinman explained. Customers expect “deeper implementation support” as they deploy AI, and the company will work more closely with customers, increase its on-site presence, create new roles, and “adapt many existing ones.” In its SEC filing, the company said it expects to continue hiring in “key strategic areas” throughout 2026.

Workers will be expected to work better, “not harder,” Zinman noted. He pointed to several past examples where work could have been done in a few days, but instead took many months with “multiple meetings and endless friction.”

“This wasn’t people’s fault and everyone was frustrated by this,” he said. “Our new org changes ownership to allow people to make decisions and move fast.”

A spokesperson for monday.com declined to comment further on the staff reductions.

Monday.com’s key market advantages

Monday.com certainly isn’t struggling; the company expects 19% to 20% year-over-year growth in 2026.

“Companies in that position do not restructure because they must,” Greyhound’s Gogia noted. “They restructure because they have decided to become something else.”

Melody Brue, VP and principal analyst at Moor Insights & Strategy, pointed out that organizational redesign is important for real AI transformation, but while it can signal confidence to the market, it can still be “devastating” to humans.

While the company looks as though it’s trying to do right, that ultimately remains to be seen, she said. “There are often hidden internal bruises that can surface long after layoffs.”

Monday.com’s advantage is in its “structured substrate,” Gogia noted; its boards, permissions and typed workflows give agents something firmer to act on than just documents and chat history. The company highlights its natively built agents that can be configured by any team member, as well as connectors with Claude, Microsoft Copilot, and ChatGPT, and dedicated routes for external agents to authenticate and operate.

“For some time, the sharper enterprise question has been shifting from who has an agent to who owns the governed runtime in which an agent can safely act,” he said. “Structured work is a serious claim on that runtime.”

But parts of monday.com’s agent estate remain in staged release, and its product is ultimately “mid-transition,” Gogia pointed out; its agent builder carried a beta label as recently as March,. Also, the company’s pricing model changed in May to a hybrid model charging for seats as well as mandatory AI credits. And, while its AI-powered no-code builder monday vibe passed $1 million in annual recurring revenue within two and a half months, monday.com has not released subsequent outcomes, usage volumes, or attach rates.

Further, there’s an element of “gravity” with its competitors, he observed. Asana is reorganizing teams around agents, Atlassian is wiring agents into the developer estate, and others are simply bundling them into their offerings: Microsoft is doing so across the productivity stack, and ServiceNow across enterprise operations, each with identity and procurement built in.

“Their pull is strongest exactly where monday.com wants to grow, in the largest accounts, where control-plane depth and administrative reach decide the deal,” said Gogia.

Actions for the near-term

Going forward, buyers should focus on operating risk, not headline risk, Moor’s Brue noted. In practice, that’s continuity of service, roadmap consistency, and strength of enterprise support. Productivity should be valued as better outcomes per unit of organizational effort, not mere activity.

“It should be a measure of how much smoother, faster, and more effective the operating model becomes when AI is built into the work,” said Brue.

Gogia noted that strain surfaces first in customer service, and monday.com’s attention is being redistributed. The company’s annual report disclosed that its focus is now concentrated on the largest accounts, with support for medium-sized clients moved to an AI-first and human-supported model.

During the first month of the transition, buyers should track named account continuity and escalation times, he advised. By the first quarter, keep an eye on whether credit governance and admin controls mature on schedule, and if the roadmap beyond the AI estate keeps pace. By the half-year mark, determine whether promised implementation depth is producing outcomes or “simply more billable engagement.”

Support tiers should be enumerated in writing before renewal, and buyers should contract for “side exits,” Gogia emphasized, with overage pricing fixed in advance, the right to pause consumption, and portability for workflows and agent configuration “if the relationship sours.” Finance should also insist on monthly consumption reporting by capability. Further, integration efforts, partner dependency, and change management should be considered first-class costs of the agent era, “not as afterthoughts to a license.”

“A license was a known cost,” said Gogia. “A meter is a behavior, and behavior is harder to forecast than headcount.”

This article originally appeared on CIO.com.

Just in time for the iPhone’s 20th anniversary, Apple is moving closer to becoming a service company. It is set to launch its new deal with Klarna next week and when it does, Apple enthusiasts in the US will effectively be able to subscribe to their favorite Apple hardware, with the cost spread across up to three years.

This matters because when combined with Apple One and Apple’s Creator Studio subscriptions, the Klarna arrangement brings Apple closer to offering a full subscription model for hardware, software, and services. The only thing you don’t get under the new arrangement is AppleCare, for which you’ll allegedly need to pay extra.

Moving closer to hardware-as-a-service

Apple has slowly been transitioning toward hardware-as-a-service for almost a decade. Back then, Forrester analyst Frank Gillet predicted the company would eventually offer bundles of services and products for a monthly, all-in, fee. 

This isn’t quite where we are yet; you still need at least three subscriptions to get close. But, after the better part of a decade, Apple has moved much nearer to the hardware-as-a-service idea.

There are some products reportedly excluded from the arrangement, including MacBook Neo, Apple Watch SE, the entry-level iPad, and iPhone 16. Clearly, Apple sees those products as sufficiently affordable. 

Easy payments for RAM-ageddon

The new Klarna arrangement comes as Apple is forced to increase product prices as AI-driven memory price inflation becomes widely felt across every economy. In theory, I assume, Apple hopes to make its products available to cash-strapped consumers who need new hardware, while also navigating a time of deep economic tumult and uncertainty. It’s thought the company has previously rejected these plans to protect normal hardware sales, but normality is a kingdom we no longer seem to possess. Interesting times. Probable inflation incoming.

“Apple Upgrade lands at precisely the moment Apple needs it,” IDC analyst Francisco Jeronimo wrote in a note seen by Computerworld. “Having just pushed Mac and iPad prices up on the back of the memory shortage, with iPhone increases widely expected in September — as well as the new iPhone foldable expected at $2,500 — Apple’s real risk is that rising prices even further can impact the upgrade cycle.” 

New age, new shopping habits

The introduction of the scheme gives consumers a way to purchase the company’s popular high-end devices when they are introduced — no doubt,at higher cost — this fall. Plus, of course, if it’s good enough for GM, it’s good enough for Apple.

It’s all about attitude, too. From Apple’s perspective, it has done plenty of the groundwork required to convince its customers that subscription payments for things you value are no bad thing. 

Reluctance to embrace “Access Not Ownership’”purchasing models has dropped dramatically since Apple — and CEO Tim Cook — first began banging the drum for services income. Apple’s services stream has now become its second-biggest revenue driver after the iPhone. It has over 1 billion paid subscriptions, and an active hardware installed base of more than 2.5 billion devices globally.

A combination of changed customer habits and external threat means the stars are now aligned for hardware-as-a-service models. “Reframing a device as a low monthly payment protects that [upgrade] cadence and allows Apple to start marketing their products as device-as-a-service to consumers, which no other vendor was ever able to do,” Jeronimo wrote to me. 

There is a one-more-thing aspect to this: the products are effectively being leased, a new approach that will give Apple a stronger grip on EOL devices, helping it grab more of them for refurbishment, resale, and recycling. Over time, this will give the company a much stronger grip on the lucrative second-user market that exists around Apple equipment, even while for almost every consumer product we find the life we want is something we can rent, but probably can’t afford to own.

Managing future risk

The other solid reason to take a partnership approach is risk management. Apple had intended to develop its own buy-now, pay-later scheme via Apple Pay Later, but abandoned that plan as it became riskier with rising bank rates. “Also, by backing the program with Klarna rather than reviving the in-house subscription plan it shelved in 2024, Apple captures the demand upside without taking the credit risk onto its own balance sheet,” Jeronimo said.

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Traditional phishing techniques are in decline as a result of the disruption of the Tycoon2FA phishing-as-a-service (PHaaS) platform, Microsoft said in a new report, “Email threat landscape: Q2 2026 trends and insights”.

“Phishing volume linked to the platform fell 92% from pre-disruption averages, including QR code phishing and CAPTCHA-gated phishing both declining from their March highs,” the company wrote in the report.

The takedown reduced activity across multiple phishing categories, forcing attackers to shift to newer delivery methods.

Riding this shift in were a few notable phishing campaigns, including an automated business email compromise (BEC) campaign that reached 42,000 organizations in under three hours, and a multi-stage phishing campaign that used nested email (EML) files, calendar invitations, and a Microsoft authentication redirect to deliver malware.

To counter phishing attacks, Microsoft recommends blocking emails containing known bad URLs/ subject fields, enabling password-less authentication methods, or moving to MFA for accounts that still require passwords.

Tycoon2FA disruption sent attackers exploring

The take-down of Tycoon2FA forced its operators to abandon portions of their infrastructure and rework hosting, domain registrations, and delivery mechanisms.

“After falling 15% in March and another 22% in April, Tycoon2FA-linked phishing volume dropped 74% in May to just 1.5 million messages, then fell another 20% in June to 1.2 million, by far the lowest monthly volumes observed in at least a year,” Microsoft said.

The decline extended to QR Code lures and fake CAPTCHA pages, two phishing techniques in which Tycoon2FA accounted for 12% and 14% of industry activity in June, respectively. This indicated that the platform’s customer base had not been able to migrate to a replacement infrastructure.

But cutting off one head of the hacker hydra only gave rise to new tactics elsewhere.

The adaptation came in the form of using Microsoft Teams as a social engineering channel. Attackers established conversations to build trust before attempting credential theft or delivering malicious payloads. “Teams-based phishing volume climbed steadily throughout Q2, with the average number of detected attacks rising 19% from March to April, holding roughly flat into May (+1%), then increasing another 10% into June,” Microsoft said.

Microsoft also observed a highly automated BEC campaign that reached over 67,000 users using scripted emails, Amazon Simple Email Service (SES), and engagement tracking, alongside a separate phishing campaign targeting 107,000 users that abused Microsoft’s authentication flow and trusted cloud services, including Teams archive recording and ICS calendar invite, to disguise malware delivery behind legitimate infrastructure.

Phishing changes but the defense doesn’t

While QR Code and Captcha-based phishing attacks dropped significantly in the second quarter, business email compromise (BEC) charted jumped 121% between March and April, before dropping down again in May.

QR Code phishing represented 8.3 million attacks in June 2026, down from a peak of 18.7 million in March. Similarly, Captcha-gated phishing fell from 12 million attacks in March to 2.2 million in June.

BEC attacks hit 9 million in March, falling to 3.9 million in June.

But even as these phishing classics lost momentum and newer techniques emerged, Microsoft’s defensive advice remained rooted in the basics. It noted organizations should complement email filtering with phishing-resistant authentication such as passkeys and phishing-resistant MFA to reduce the effectiveness of credential theft campaigns.

The company also recommended strengthening Exchange Online Protection and Microsoft Defender for Office 365 with capabilities such as Safe links and Zero-hour Auto Purge (ZAP), in which malicious emails already delivered to mailboxes are removed before they are read, alongside enforcing password-less authentication methods like Windows Hello, FIDO keys, and Microsoft Authenticator.

Microsoft concluded its report with a list of indicators of compromise (IoCs) from the threats observed in the quarter to support detection efforts.

This article first appeared on CSO.

Every CIO I speak with today is wrestling with some version of the same question: How do we move faster with AI and deliver on our commitments?

It’s an understandable concern. Boards and CEOs are asking about AI. Business leaders are experimenting with use cases. Employees are discovering tools daily, while technology vendors promise unprecedented gains in productivity, innovation, and competitive advantage.

After hundreds of conversations with technology executives over the past year, I’ve become convinced that speed isn’t the real issue. The organizations pulling away from the pack aren’t necessarily adopting AI faster than everyone else. They’re executing more effectively — a subtle distinction that represents one of the defining leadership challenges of the AI era.

Technology has never been the hardest part of transformation. People, priorities, culture, and operating models are the biggest challenges. The ability to translate bold boardroom aspirations into thousands of thoughtful decisions made every day by architects, engineers, product managers, analysts, and business leaders is where competitive advantage is created. AI may be accelerating the pace of change, but it hasn’t changed that fundamental truth.

I’ve met plenty of executives who are exceptional in the boardroom. They know how to frame a vision, influence a board, and build confidence among investors and business leaders. I’ve also met remarkable technologists who instinctively understand the architectural decisions, engineering tradeoffs, and implementation details that determine how great ideas become reality. Modern CIOs, however, must move comfortably between both worlds. Afshean Talasaz is one who stands out among this rare breed.

Long before becoming CIO of Colonial Pipeline, Talasaz built his career from the ground up as a business professional, data scientist, and technologist. He has designed enterprise platforms, built AI capabilities, led technology organizations, and partnered closely with executive leadership teams on business transformation. Today, as an executive in residence with our Practitioners for Practitioners (P4P) community, he helps CIOs and business leaders navigate one of the most significant technology shifts of our generation.

While Talasaz brings deep knowledge of data and AI to the table, his greatest strength is his ability to create strategy and connect it with execution. He can spend the morning discussing enterprise reinvention with the board and the afternoon debating architectural principles with the teams responsible for bringing that vision to life.

That versatility gives Talasaz a unique lens on how CIOs can deliver value with AI.

Software companies have a term for engineers who understand every layer of the technology stack: full-stack developers. Listen to Talasaz and it becomes evident that the AI era requires something similar from technology leaders: a full-stack CIO.

The full-stack CIO: Leading with clarity

A full-stack CIO understands how every layer of the enterprise influences the next. They recognize that every strategic priority becomes a portfolio investment, every investment shapes an operating model, every operating model influences architecture, every architecture choice informs product decisions, every product decision shapes engineering priorities.

The best CIOs understand both ends of that journey. The extraordinary ones understand everything in between.

And those who execute best lead with clarity, Talasaz says.

“Everyone, from executives to middle managers to the people writing code, should be able to explain what we’re trying to achieve,” he emphasizes. “Clarity isn’t that we’ve handed out the PowerPoint. It’s that people genuinely understand where we’re going and can articulate it in their own language.”

One of the unintended consequences of the AI boom is that organizations are beginning to confuse activity with alignment. They have AI councils, AI governance committees, AI innovation labs, AI centers of excellence, AI pilots, and AI roadmaps. Yet if you stop ten people in the hallway and ask a deceptively simple question, What business problem are we actually trying to solve? you’ll often hear ten different answers.

As a result, architects optimize for one objective while product teams optimize for another. Business units pursue opportunities that seem perfectly reasonable from their perspective. Engineers make thoughtful technical decisions based on the information available to them. Individually, none of those decisions are necessarily wrong. Collectively, however, they create organizational drift. AI doesn’t create that problem. It simply accelerates the consequences.

And while AI can be a force multiplier for the positive when every decision is guided by a shared understanding of where the organization is headed, it can also be a force multiplier for the negative, resulting in an organization simply moving faster in different directions.

“When we have the fundamentals right, the tech infrastructure, the operating models, the nuances of how our business actually runs, we get the impacts of AI in a positive way,” Talasaz says. “When we don’t have those in place, AI can amplify the gaps or mute the benefits.”

At a time when so much of the conversation surrounding AI is focused on algorithms, agents, and automation, it’s an important reminder that organizations don’t execute strategy; people do.

Reducing organizational friction

Most executives are familiar with the concept of VUCA that characterizes today’s business environment. But Talasaz stresses the importance of turning this concern inward: “If the world outside our organizations is becoming more volatile, uncertain, complex, and ambiguous, what are we, as leaders, doing to the inside of our organizations?”

Leaders spend enormous amounts of time helping their organizations respond to external disruption but comparatively little time asking whether they are inadvertently re-creating those same conditions internally in response to those external needs. Are we reducing uncertainty or introducing more of it? Are we simplifying work or adding unnecessary complexity? Are we helping people focus on what matters most, or asking them to navigate competing priorities and shifting expectations?

Talasaz refers to this phenomenon as double VUCA — something I’ve witnessed repeatedly while working with CIOs over the past decade. Organizations often assume they’re struggling because of technology limitations when the real constraint is organizational friction. Teams wait for decisions. Priorities shift faster than roadmaps. Governance grows heavier. New committees are formed to solve problems created by existing committees. Everyone is working harder, yet the organization somehow feels slower.

AI amplifies both outcomes. Organizations with clarity become dramatically more effective because AI accelerates good decisions. Organizations without clarity simply accelerate confusion.

Operating model as strategy enabler

AI governance is one way to achieve greater clarity, but as Talasaz says, governance shouldn’t primarily exist inside policy manuals that few people read.

Instead, AI governance should be embedded in the daily rhythms of the organization, shaping how teams collaborate, how decisions are made, how products move from ideas into production, and how innovation happens safely without requiring constant escalation. In other words, it’s all about your operating model.

“If you had to pick one thing that isn’t technology, your operating model is the most important element for executing data and AI at scale,” he says.

The best operating models create enough clarity that capable people can make thousands of decisions independently and confidently, without having to wait for permission. By embedding good governance into the way it works, the organization becomes faster.

This advice echoes something I’ve heard repeatedly from some of the world’s most respected CIOs: High-performing organizations aren’t built on tighter control; they’re built on greater trust, supported by clear principles, shared expectations, and operating models that enable responsible decision-making at every level of the enterprise.

Talasaz points out that technology leaders tend to speak in terms of transformation. He suggests CIOs consider a different word: reinvention.

As he explains, transformation implies replacing what exists today with something new. Reinvention starts with a more clear-eyed and practical premise: Some things absolutely must change; others represent years, sometimes decades, of accumulated expertise, customer trust, operational discipline, and competitive advantage.

Reinvention is about building on those strengths while also creating new ways to deliver value. The leaders making the greatest progress in their AI journeys seem to recognize that it’s less about abandoning the past than thoughtfully preparing the organization for the future.

Closing the gap between strategy and execution

Full-stack CIOs must be able to map out the various layers of execution and planning that need to be done at every level of the organization to be successful. To help with this, Talasaz has developed a data and AI framework that draws on his own experiences “from the keyboard to the boardroom.”

As Talasaz sees it, too many organizations have been doing good work in isolation. “They’re doing a lot of the right things,” he says. “They’re just not connected.”

Boards may be discussing growth while business leaders redesign customer experiences. Product teams may be prioritizing new capabilities while architects modernize platforms. Data teams may be improving quality while engineers focus on delivery. Every group makes meaningful progress within its own domain, yet somewhere between strategy and execution, the connective tissue begins to disappear. Talasaz’s framework brings those connecting points to the forefront.

Crucially, the framework doesn’t begin with technology or AI or even with data. It begins with the experiences the organization hopes to create for its customers, employees, or partners. Many AI initiatives start with the question, “What can this technology do?” And indeed, we need to be inspired by the possibilities and challenged to think differently by what the technology can do. But, Talasaz emphasizes, we also need to ask what experiences we need to deliver for our business and how the technology can make that a reality.

The framework challenges CIOs to answer that question first. Only after the experiences are clearly defined does the conversation move to the capabilities required to deliver it, the business activities that support those capabilities, the AI and data products that enable them, and finally the data foundation that makes everything possible.

This shift in perspective ensures that, rather than allowing technology investments to search for business value, the business experience defines the technology required to deliver it. For CIOs, that’s more than a planning exercise. It’s a fundamentally different way of leading.

Over the coming months, the P4P community will be convening a series of small CxO roundtables to explore these issues and work more deeply with Afshean Talasaz’s 6×6 Data and AI Framework. CIOs and other enterprise leaders interested in participating are welcome to reach out to me directly.

Cloudflare recently beat Q1 2026 earnings. Revenue up 34% year over year. EPS ahead of consensus. Full-year guidance raised. Then, in the same breath, they announced 1,100 layoffs, 20% of the company. CEO Matthew Prince’s explanation: “The way we work at Cloudflare has fundamentally changed.”

Block did the same thing. Beat guidance, raised outlook, cut 4,000+ jobs. Both framed it as architecting for the AI era.

This is not a contradiction. This is the new math boards are running. And if you’re a CIO who hasn’t started running it yourself, you’re behind.

The benchmark has moved

AI-native companies have quietly reset what “efficient” means for a technology organization. Midjourney generates over $500M in revenue with roughly 160 employees, over $3M per head. Anthropic hit a $14B annualized run rate in early 2026 with fewer than 3,000 employees. Across the top AI-native startups, the average revenue per employee is $3.48M, nearly twelve times the traditional SaaS benchmark of $300K.

Boards aren’t comparing you to your 2019 self anymore. They’re comparing you to Anthropic.

This is the pressure Cloudflare and Block are responding to. They’re not cutting people because the business is struggling. They’re cutting because investors have internalized a new denominator. Headcount is no longer a proxy for capacity; it’s a liability on the efficiency ratio.

For CIOs, this creates a hiring problem that looks nothing like the cloud or mobile talent gaps of the past decade. Those gaps were about volume: hire 100 cloud engineers, absorb the cost, build the capability… This one is about density; you’re not looking for 100 people. You’re looking for 10 who can deliver what 100 couldn’t, and justify $1M or more in value per seat.

Finding bodies to fill seats has never been easier. Finding people who operate at that level of leverage is a different problem entirely.

‘Acqui-hires’ are a shortcut with a hidden cost

Companies have figured out that recruiting AI-native talent one by one is too slow and that it’s faster to buy a team. Google’s acquisition of the Windsurf founders, Meta bringing in the Scale AI team, Accenture’s string of AI-focused acquisitions: these are acqui-hires dressed up as M&A. The premium on experienced AI talent is high enough, and the urgency real enough, that organizations are skipping traditional hiring loops entirely and buying their way in.

I’ve been on the other side of this. My company, MadKudu, was acquired by HG Insights specifically to bring AI-native capability into an established enterprise business. HG needed change agents who had already figured out how to build and ship in this new era, not just people who’d read about it. That’s the thesis behind most of these deals.

But there’s a cost that doesn’t show up in the acquisition price.

AI-native teams are fast because they operate with a different set of defaults: full access to tools, minimal governance layers, the ability to experiment and ship without a six-week approval cycle. That operating model is not a perk; it’s the fundamental mechanism. It’s why a team of 10 can do what an enterprise team of 100 can’t.

When you acqui-hire that team and then slot them into your existing approval processes, you’ve bought the people and killed the engine. The change agents you paid for become change-frustrated. The attrition that follows is expensive and predictable.

The harder realization: acquiring an AI-native team means accepting how they work. That requires deliberately carving out space for them to operate differently, not just tolerating it but institutionalizing it. The acquisition is an organizational change program, not just a hiring event.

The CIO’s real problem

The governance stack most enterprise organizations run was designed for a headcount world. Every tool vetting cycle, every vendor review, every security approval was calibrated assuming you were managing a large team where consistency and control were the primary objectives.

That calculus breaks when your goal is talent density. The same approval processes that protect against data leaks are now the reason your best people can’t do their best work. When it takes six weeks to approve a tool that your competitor’s team is already shipping with, you’ve traded velocity for the perception of safety.

The practical fix is structured experimentation: clear guardrails, defined boundaries, but explicit permission to try tools before deciding whether to roll them out broadly. Gating everything prevents you from ever discovering what 10x productivity looks like.

The skills inventory question is also more nuanced than it sounds. Job titles won’t tell you where the leverage is. You need to map the actual tasks within each function and assess which can be automated or augmented with AI. That’s where you find the people who, with the right tools, become your $1M/employee talent, not because you hired differently, but because you enabled better.

This is also where the build-versus-buy question gets genuinely tricky. As AI reshapes how products are built and delivered, your internal operating model — how you work, how fast you ship, how you use data — is becoming core IP. Outsourcing delivery means outsourcing the part of the organization where your competitive advantage is now being built.

Closing the gap without slowing down

The AI talent wars are not primarily a recruiting problem. They’re a rethinking of what organizations are supposed to look like.

Boards have a new benchmark. Cloudflare, Block, Amazon, Meta and others have already started restructuring to meet it, publicly, painfully, even while beating their numbers. The question for CIOs isn’t whether this pressure arrives; it’s whether you’re ahead of it or behind it when it does.

The organizations that navigate this well won’t win by outbidding competitors for a handful of elite engineers. They’ll win by designing operating systems that amplify the leverage of the talent they do have, by enabling their best people rather than constraining them, and by treating AI fluency as a core organizational capability rather than a niche specialization.

Talent density is the new headcount model. The sooner your governance, your tooling and your board conversations reflect that, the better positioned you’ll be when the next efficiency report lands.

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I have worked alongside enterprise technology for more than 30 years and watched AI evolve from a lab experiment into the modern boardroom’s core focus. However, the last few years of implementing AI alongside our customers have delivered our most profound reality checks.

The initial hype has faded, leaving CIOs to drive real enterprise value. Based on my experience implementing Google, OpenAI and Anthropic technologies, here are the fundamental, technology-agnostic lessons every leader must anchor their strategy around.

AI as a leadership multiplier

The most common tactical error we see is treating AI as an isolated technology project. What I have observed among our customers is that true success does not come from organizations that define a standalone “AI strategy,” but rather from those leaders that integrate AI into their business strategy.

When our customers isolate AI and define an AI strategy, it inevitably treats it like a “technological toy” to experiment with. This approach yields fragmented, orphaned initiatives that fail to scale because they are fundamentally disconnected from their core corporate objectives. What I learned is that AI is not the ultimate destination; it is a powerful catalyst. We have replaced “What can AI do for our customers?” with a more strategic question, “How does AI accelerate their existing business goals?”

Think of AI like electricity. No modern corporation designs a standalone “electricity strategy.” Instead, all companies route it invisibly across the entire organization to illuminate offices, power production lines and drive communication. AI must be woven into the enterprise fabric in the exact same way, acting as an underlying utility that supercharges your existing operational model.

Integrating AI into the broader business strategy also dictates how we measure success. It forces a shift away from short-term tech vanity metrics and anchors the technology into a long-term roadmap.

When AI remains trapped within the IT department of our customers, we notice that it is relegated to a mere “software experiment.” To become a true competitive advantage, we observed that AI requires intense cross-functional orchestration. This perspective does not diminish the merit of the technical team; their expertise is fundamental for establishing the architecture, data governance and tools your enterprise requires. However, while IT builds the foundational infrastructure, it lacks the organizational authority to decide what should be built on top of it. Only the CEO or the owner of the company can step in to ensure AI leaves the “toy project” phase and integrates into the DNA of the organization.

The requirement for top-down, executive ownership stems from three critical realities observed in the field:

• Silo-smashing and data collaboration: True enterprise AI is data-hungry and that data lives across disparate business lines, finance, operations, marketing and customer service. Only the CEO possesses the cross-functional authority to demand that data silos be dismantled.
• Cultural transformation and fear mitigation: AI triggers widespread anxiety over job displacement across all industries and hierarchies. When relegated to an “IT project,” resistance spikes as teams view it as a threat to their livelihoods. When I saw the CEO lead this cultural shift directly is when I noticed the best results.
• C-Suite education and strategic alignment: The mandate for AI capability cannot just be delegated downward; the transformation must begin at the very top. I have conducted more than 70 presentations for the Board of Directors and C-Level teams. These people need to be actively educated not on technical code, but on specific business use cases, return on investment (ROI) frameworks and how AI resolves core organizational bottlenecks.

PwC’s data found that only 12% of enterprises have achieved both cost and revenue benefits from AI. Those elite 12% succeeded precisely because their CEOs embedded AI extensively across strategic decision-making and cross-functional workflows. AI is simply too disruptive and too critical to be left exclusively in the hands of technical experts. If AI is not on the CEO’s weekly agenda, it is fundamentally missing from the company’s true strategy.

AI as a new operational framework

Traditional IT systems have operated on strict algorithmic certainty: if you input a specific set of data, the system executes an immutable line of code and guarantees the same, predictable output every single time.

AI completely breaks this paradigm. Because modern AI is built on probabilistic models, it does not execute static formulas; instead, it predicts the most likely correct response based on mathematical probabilities. This means that AI solutions carry an inherent, small percentage of uncertainty and variability. A prompt entered today might yield a slightly different, though contextually valid, output tomorrow.

Executive leadership and organizational cultures must be actively educated to accept and navigate this fundamental shift. Traditional quality assurance frameworks for software are designed for a 100% success rate. Applying this rigid standard to AI will paralyze your initiatives, keeping 80% of your projects trapped eternally in the pilot phase. This happened to us in a food and beverage company in Latin America a couple of years ago. After this experience, we started to include conditions in our contracts that tolerate statistical margins of error and still define the project as a success.

In terms of cost calculation, we had to teach CIOs and business managers to forget the monthly subscription model for AI and learn to manage the primary unit of exchange in modern AI: the token.

To understand AI costs, executives must understand how large language models process data. AI models do not read full words; instead, they break text, images or code down into “pieces” called tokens. As a baseline, every 100 words process as approximately 130 to 140 tokens. Because the major AI providers use the token as their currency, your business is billed dynamically based on the exact volume of tokens consumed by every query submitted (input) and every response generated (output).

Many leaders believe AI costs are fixed due to flat-rate enterprise tiers ($25–$30/user). This is a temporary illusion. These venture-capital-subsidized rates mask true operational costs and come with dynamic usage limits. Modeling long-term ROI on them guarantees a severe budget shock when true consumption pricing takes over.

The solution is not to halt AI adoption; doing so means losing your competitive edge. Instead, the cost per token must cease to be treated as a technical footnote relegated to the IT department. It must be elevated to a core business variable.

Risks in the AI adoption model

Since the beginning of the AI boom, I have seen all our customers making a critical tactical error that could cost them heavily in the medium term: they are focusing only on operational efficiency (reducing costs with AI).

I have observed that an alarmingly high percentage of companies remain trapped in pilot phases focused exclusively on short-term cost reduction. Bain & Company’s global Automation and AI Pathfinder Survey found that the largest share of companies measuring their AI initiatives (exactly 40%) realized cost reductions of 10% or less, heavily missing their internal targets. Our customers are putting too many resources and effort into marginal financial gains and in doing so, they are jeopardizing their most valuable assets: service quality, resilience and customer trust.

Utilizing AI solely to slash headcount or cut operational corners is a dangerous trap that introduces severe field liabilities. A financial service organization in Latin America announced that they saved $1 million in customer support by replacing humans with AI chatbots. However, the mid-term reality revealed a different story: a damaged brand reputation due to AI errors and an influx of frustrated clients fleeing because the automated system cannot handle special cases.

Putting a company on an extreme AI diet might make it look leaner on next quarter’s financial statement, but over-indexing on cost-cutting will ultimately leave the business too weak to compete when market dynamics shift. We are now inviting our customers to change the question from “How much money will AI save us?” to “How will we leverage AI to exponentially increase the long-term value of our enterprise?”

Deploying enterprise AI is a marathon, not a sprint, and the terrain changes with every mile. The organizations that thrive in this next era will be those that transition from fascination to discipline, treating AI not as a magic bullet for immediate savings, but as a core capability that demands rigorous governance, architectural foresight and cultural maturity. Navigating this shift requires moving past the theoretical hype and anchoring decisions in raw, field-tested reality.

As we continue to deploy these technologies across industries, the blueprint for success is being rewritten in real time. Let’s keep this conversation going as we map out the future of business intelligence together.

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Late in a large enterprise SAP transformation, the strategic governance conversations began to drift. Instead of executive decisions, we found ourselves debating whether the program needed dedicated testing, whether cutover required a full weekend, whether twenty Agile teams really needed coordination support and whether offshore resources were adding value at all.

The questions were not coming from the delivery teams. They were coming from the executive sponsor.

The sponsor had recently been elevated into a senior leadership role and had never sponsored a technology transformation at this scale. The challenge was not authority. The sponsor had every right to ask any question they wanted. The challenge was that strategic governance had quietly turned into a debate about delivery practices, because the sponsor did not yet have the transformation context to focus the conversation anywhere else.

This is not a story about a bad sponsor. The executive in this case was a capable senior leader with strong judgment and authentic intent. They had been placed into a role they had not yet been prepared for, and the pattern that followed was structural, not personal. It is one of the more common patterns I have observed across enterprise transformation programs, and one of the most consistently misdiagnosed.

Most program failures are not execution failures. They are sponsor mismatches.

When governance becomes a debate about delivery practices

When the sponsor does not understand what an enterprise transformation actually requires, governance forums stop functioning as decision bodies and start functioning as practice debates.

You see it in the questions that get asked. Why do we need a dedicated testing phase? Can the Build timeline be compressed? Why does cutover need a full weekend? Why do we need more Scrum Masters across 20 product teams? Can the US team simply work longer hours instead of using offshore resources? On one program, the sponsor suggested shifting the entire project’s working hours to India time, despite roughly 85 percent of the delivery organization being based in the United States.

None of these questions are unreasonable in isolation. Each one targets a real cost or timeline pressure. The problem is what is missing underneath them: an understanding of the operational risks the original choices were designed to mitigate.

When sponsors ask delivery-practice questions without that context, the program leadership team ends up defending the work instead of advancing it. Decision velocity drops. Trust between the program and its sponsor erodes. Senior delivery talent disengages from governance forums where the conversation never reaches the decisions they need made. What looks from the outside like an active sponsor producing engagement is, from inside the program, an active drain on the cycles needed to deliver.

The compounding cost is not unique to any single program. PMI’s research on executive sponsorship consistently identifies sponsor engagement quality, rather than sponsor presence alone, as one of the strongest predictors of project success. The visible symptom is debate. The actual cost is unmade decisions.

Authority is rarely the issue. Literacy is

When transformations stall under a mismatched sponsor, the diagnostic instinct is to question the sponsor’s authority. Are they senior enough? Do they have the cross-functional reach? Can they unblock?

In most of the programs I have led or advised, authority was not the limiting factor. The sponsor in the SAP program above had ample authority. They could unblock any decision the program needed. What had not been developed was the transformation literacy to know which decisions mattered, which were technical noise and which were execution risks that should not be optimized away.

This is what I have come to think of as the literacy problem. Sponsors elevated into transformation roles often have deep functional expertise (finance, operations, business unit leadership) but limited exposure to the distinct functions of PMO, organizational change management, agile delivery, testing and cutover, and how each one reduces a specific category of implementation risk. They are not expected to be SAP configuration experts. But they need enough transformation literacy to recognize which questions actually belong in a steering committee.

Harvard Business Review’s research on effective executive sponsorship has emphasized that sponsorship effectiveness depends as much on judgment as on authority. Judgment is where literacy becomes operational. A sponsor with authority but limited transformation literacy will optimize for speed and cost in ways that consistently underestimate risk. A sponsor with both will make the tradeoffs the program actually needs.

Prosci’s longstanding benchmark studies on change management have ranked active and visible executive sponsorship as the single greatest contributor to change success for two decades. The word that matters in that finding is active. Active sponsorship without transformation literacy can introduce real cost. Not because the sponsor is acting against the program, but because the optimization choices they make are based on incomplete information about what the program is built to protect against.

Shift the conversation from delivery practices to business risk

When the sponsor relationship is already in place and cannot be changed, the program leadership team has one move that consistently works: shift the conversation.

On the SAP program above, we stopped explaining why the testing phase existed. We started explaining the business risk of reducing it. We stopped debating the number of Scrum Masters. We started connecting delivery capacity to coordination across more than twenty Agile teams and the business cost of losing that coordination. We reframed offshore support as a way to maintain delivery momentum around the clock rather than asking the U.S. team to sustain fifteen-hour days.

The shift is from defending delivery practice to explaining business risk. The sponsor does not need to understand why testing takes the time it does. They need to understand what the program is exposed to if testing is compressed. They do not need to know how many Scrum Masters are statistically optimal for twenty Agile teams. They need to know what coordination breaks when the number is wrong.

This reframing accomplishes two things. First, it brings the conversation back to the level at which sponsors actually make decisions: tradeoffs between business outcomes and business risks. Second, it builds transformation literacy in the sponsor over time, almost as a byproduct. By the third or fourth iteration of business-risk-framed conversations, the sponsor begins to ask the right questions on their own.

In practice, this happens through small but deliberate moves. When the sponsor asks why a phase needs the time it takes, the program lead names two or three things that could go wrong if the time is cut and what each would cost the business. When the sponsor asks why a role is needed, the program lead names the work that would not get done without it. Every delivery-practice question gets converted into a business-risk answer.

The program leadership team’s job is not to make the sponsor an expert in SAP delivery. It is to provide enough transformation context so that executive decisions reflect both business priorities and implementation realities.

There are a few phrases I have used with executive sponsors over the years that capture the underlying issue. The sharpest one:

If the decision has to go above the sponsor, they are not the sponsor.

Sponsorship is defined by what the sponsor can decide without asking someone else. That is the test. Anything else is the appearance of sponsorship, not the substance.

For CIOs supporting enterprise transformation, the implication is direct. Sponsor selection, or sponsor preparation when selection is not an option, is not a hierarchy question. It is a transformation capability question. The same execution discipline that goes into defining decision rights, structuring governance and protecting delivery momentum should apply, with equal rigor, to assessing sponsor fit and building sponsor literacy before the program begins.

A sponsor does not need to be the technical expert. They do need to know when to trust the people who are.

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