Providers and deployers of AI systems: You only have a couple of weeks left until you must explicitly inform users when they are interacting with AI content.

To assist in the effort, the European Commission (Commission) has published guidelines to help AI deployers get in line with the AI Act’s transparency obligations, which will begin to go into effect on August 2.

After that, companies providing AI systems must alert users when they are interacting with AI. They must also tell users when they have been exposed to deepfakes, “emotion recognition,” or biometric categorization systems, or when they are given AI-manipulated content in matters of “public interests without human review or editorial control.”

Henna Virkkunen, the Commission’s executive VP for tech sovereignty, security and democracy, said in a statement, “with today’s guidelines, the Commission supports the smooth and effective application of the AI Act to make AI systems interacting with people such as chatbots and AI agents and AI content more transparent and trustworthy. These guidelines support providers and deployers in meeting their obligations under the AI Act, while helping citizens know when they are interacting with AI.”

Systems must include machine-readable markers to reveal such content, to reduce “the risk of deception and manipulation” and build public trust in AI.

“Generative systems have collapsed the cost of producing convincing content while the cost of judging it stands where it always stood,” said Sanchit Vir Gogia, chief analyst at Greyhound Research. This requirement is “an attempt to restore friction to that imbalance.”

A company’s non-compliance could result in fines anywhere from €750K (about $856K) to €15M (about $17 million), or even up to 3% of its total worldwide annual revenue.

Transparency requirements

The EU AI Act’s transparency requirements apply to “natural or legal persons,” public authorities, agencies, or other bodies that develop AI systems, or have them developed, and place them on the EU market or into use under their name or trademark. This means all companies, regardless of whether or not they are EU-based.

“Systems placed on the European market, put into service there, or producing outputs used there are inside the field, wherever the developer sits,” Gogia noted.

Applicable systems must be intended to interact directly with “natural persons”; these systems include AI-enabled chatbots or conversational agents, AI companions, or coding agents. However, AI-enabled tools like recommender systems, spam filters, authentication, search and retrieval, transcription, text and code auto-completion, or predictive maintenance do not fall under the rule.

Specific outputs such as AI-generated text, images, video, and audio must contain a machine-readable mark. Deepfakes and public interest-related text created by AI without human review or control must be clearly labeled, however, deepfake content that is “artistic, creative, satirical, or fictional” is largely exempt.

AI content must be marked with one of three labels: “AI,” “Fully AI-generated,” or “Partially AI-modified.” For instance, “Fully AI-generated” applies when news summaries, music, art, or videos have been created without any human oversight (apart from prompting), while “partially AI-modified” could mean a person’s face is swapped into an authentic photograph to create a deepfake.

The three icons are publicly available for free use; enterprises can download zip files in PNG and SVG formats.

Most of the Act’s transparency rules begin to go into effect on August 2. But AI systems placed on the market before then will have some leeway; they must be in compliance by December 2.

However, a four-month allowance “on one obligation, for one population of systems, contingent on one procedural step, is not a strategy,” Gogia emphasized. Enterprises should plan to comply by August 2 and “treat any relief that arrives as margin.”

A consistent code of practice

Along with the transparency guidelines, the Commission has introduced a code of practice that essentially serves as a gesture of good faith. When signed, it can provide “legal certainty” and a “simple and practical” way to demonstrate compliance with the AI Act, according to the Commission. Signatories can also collaborate through the ‘Signatory Taskforce,’ which will share practices and advance technologies around marking and labeling practices.

Providers that choose not to sign must comply through other methods and demonstrate that those methods are “adequate” through assessment by surveillance authorities, according to the Commission.

Non-signatories “keep their flexibility, and will face more case-by-case scrutiny for it,” said Gogia.

Criteria for compliance

Shashi Bellamkonda, principal research director at Info-Tech Research Group, pointed out that the transparency requirements apply to content only when three criteria are met: It has been published, is informative to the public, or is on matters of public interest.

B2B business content or blogs may not need an AI disclosure if they do not meet these criteria, he noted. Also, published text that has undergone human review or is under editorial control does not need to be labeled. Editorial control means that a person must hold the ultimate legal responsibility for the publication of the content.

Many companies like Google, Adobe, and LinkedIn have already established ways to identify images marked as AI-generated. Meta has made it a requirement, but the creator has to add the AI-generated label, Bellamkonda said.

“This is a good move for guardrails around public information, and companies with good compliance and ethical oversight may not have to worry about this,” he noted. But as a general practice, companies should disclose AI-generated content and state whether it has been human reviewed.

Creating a transparency pipeline

Establishing full transparency means identifying who carries the responsibility for the content, whether the marking survives real use, not just testing, and what evidence will defend the decision, Gogia said.

Concerns cluster around responsibility, durability and evidence. Several organizations usually touch one piece of content, and none controls the whole chain, which is why contracts become the “pressure point,” he said. Most current agreements were written to deliver software and say “almost nothing” about provenance persistence, verification access, or evidence retention.

The durability concern is the most difficult, Gogia noted, because marking performs well in controlled settings but “badly in ordinary life.” Meta, for one, said its invisible watermark was designed to survive cropping; a published test, however, found the company’s preview detector missed 55% of cropped images.

“CIOs should ask which platform can actually provide evidence before believing its dashboard,” said Gogia.

Disclosure of AI use must be “clear, distinguishable and accessible,” he emphasized. “A notice buried in lengthy terms, or reachable only through determined clicking, satisfies nobody, least of all a market surveillance authority.”

Sustained compliance is a “living control” requiring a central record of systems, duties and evidence; testing taking place where the user meets the control rather than where the developer built it; and continuous supplier assurance. Enforcement will vary by country, so keep one common baseline with local overlays, Gogia said.

His advice: Inventory every system that talks to people, generates content, or gauges sentiment; classify provider and deployer roles; place disclosures at first interaction; define substantive human review; keep the evidence.

Marks and provenance signals should be tested after content undergoes cropping, compression, translation, transcription, and other editing, Gogia said. A useful audit starts from a real output and follows its “pulse” through generation, editing and publication, identifying at “each beat” the responsible party, the surviving mark, and evidence for exceptions. Missed labels should also be traced for root cause and recurrence.

To ensure compliance, before August 2, enterprises need a prioritized inventory, live disclosures on the highest-risk use cases, and a “named owner for every control,” he noted. In the first 30 days, they should stabilize and test; in the first 90 days, push requirements into procurement processes as a standing discipline. Procurement must secure commitments on marking methods, known failure modes, and evidence access, with explicit notice if/when any of them change.

“The sensible architecture is a common transparency baseline carrying traceability, responsibility, and evidence, with jurisdictional overlays for language, sector rules, and local practice,” Gogia said.

This article originally appeared on CIO.com.

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.

When it comes to building an effective AI stack, context is king and power isn’t everything it’s cracked up to be.

“Smaller, smarter, safer — this is a bet our company has taken in how we deploy AI internally,” said Ricky Thakrar, head of sales and account management at Zoho, provider of a suite of popular cloud-based software solutions for sales, marketing, and finance.

“I’m on the business side, and so decisions made by our CIO and IT folks affect me directly, and my teams’ workflows and processes,” he added.

Speaking to a room of tech leaders at the CIO 100 Leadership Live New York event last week, Thakrar explained that every company wants the speed of AI-generated work wedded to the quality of human work, even though these two are diametrically opposed. No amount of model upgrades or spend will close that gap, so the only way forward is to architect your way out. Thakrar encapsulated this idea in a simple formula:

• Smaller: Stop deploying maximum firepower on every task. Many tasks don’t need it.
• Smarter: The system around the model decides more than the model does.
• Safer: Verify at the point a mistake gets locked in, not just downstream of it.

He noted that organizations that win with AI won’t be those deploying the biggest, most powerful models or the most sophisticated architecture, but the ones that figure out that the model is the easy part and the right architecture is harder. That means understanding the hardest element, and the biggest differentiator, is building a human system that learns and compounds alongside agentic systems.

To get it right, organizations need to prioritize the context layer. The size of frontier models like the GPT series, Claude, and Gemini mostly exist to compensate for missing context, Thakrar explained. Without enough context, models need to be able to reason harder and infer more about what a user actually means because it doesn’t know the user’s account, process, or history. A rich context layer makes it possible for enterprises to run workloads on much smaller, lower-power models.

“The intelligence moves from the model into the architecture around it,” he said.

A steep learning curve

One of Zoho’s earliest AI agents was a churn management agent to help the account management team detect churn in customer subscriptions. So when a subscription became inactive, the agent would collect context from notes, meeting recordings, and Zoho’s data enrichment tool, then create a summary of reasons the account might have churned, and schedule a call.

“What happened was I got this churn agent a couple months later, already embedded in our CRM, and within a week my team no longer trusted that agent,” Thakrar said. “The reason is we forgot to collect one very key point.”

In Zoho’s CRM, when a customer buys a bundle of products, that bundle is represented as a single line item. That means the status of any products the customer may have previously purchased individually changes to inactive as they’re moved to the bundle. That’s not churn, but it was interpreted it that way. Zoho fixed it in the second version of the agent.

Then a new problem arose. Many potential customers first purchase Zoho products as pilots or sandboxes. As those customers move from pilot to live instance, they close down the pilot versions. And again, the CRM would record that as subscriptions going inactive.

“The trust deteriorates again because everyone got excited for version 2,” Thakrar said.

Sometimes, a certain product might not be the best fit for a customer and Thakrar’s team will suggest the customer move to another product. That’s deliberate churn, not a churn risk.

“You may have a similar story like this where the agent sounds so good, it’s going to do something quick and add value, but it’s missing context from the account managers, and there are so many more pieces we’re still building out,” Thakrar said. “It’s been almost a year and the problem I have is my team still doesn’t trust it. They’ll see [a message from the agent] and go out and do all the research anyway to make sure it gave the correct answer.”

The team is more on top of potential churn, though, but the promised productivity gains have yet to materialize because the agent has to earn back lost trust due to a lack of context.

“My goal for this year is having an AI-assisted customer journey from sales to account management where the handoff is clean, the context flows, and every piece of information we gather about a customer is weighed, identified, and coached so the sales team can close more deals,” he said.

Zoho’s early experience with agents has led to the idea that constrained, context-rich, deterministic architectures consistently outperform expensive models bolted onto fragmented systems. It all comes down to three pillars: routing, harness, and specialization.

Routing

Routing is about sending workloads to the proper model for the job, which entails providing enough context to a given task that a small, cheap model can handle it without the need for spare reasoning capacity to fill gaps.

Frontier models are expensive and companies can burn through a year’s budget worth of tokens in months. But most tasks can be handled by much smaller, more constrained models at a fraction of the cost.

“You don’t always have to pay the frontier guys for every task,” he said. “We’ve observed with some clients that we could save them 95% with a 3 billion parameter model.”

Harness

An AI agent harness is the software infrastructure scaffolding around an LLM that differentiates an agent from a chatbot. It’s what enables an agent to act on tasks rather than simply respond to prompts. A model reasons through a problem and decides what to do about it. The harness connects the model to the tools, systems, memory, guardrails, and execution environments required to perform the actions determined by the model. The term is frequently used more or less interchangeably with orchestration layer.

“It’s the process around the model, which matters way more than the model itself,” Thakrar said.

In benchmark tests, a superior harness on a less powerful model produces better results than an inferior harness on a much bigger model.

For the best results, Thakrar said, it’s essential to understand the deterministic and non-deterministic elements of a given workload, and build that into the architecture. Machines can read, organize, and validate, and they excel at deterministic tasks. Humans, on the other hand, are exceptional at non-deterministic tasks like judging, synthesizing, and deciding.

Those non-deterministic tasks in a process are the ideal point for AI agents to incorporate a human in the loop, what Thakrar calls human harness. He pointed to a stakeholder mapping agent Zoho built for sales as an example, which takes the context of an initial meeting and third-party enriched data like a LinkedIn profile, weighs probabilities, and makes an educated guess about the stakeholder map.

“The initial goal was just to eliminate that task completely from the human workflow,” he said. “The stakeholder map is done, it’s in the folder, and you can look at it.”

But the agent would struggle to capture nuance. The meanings of titles in organizations always vary, and the politics and dynamics of any given meeting can be difficult for an AI agent to discern. Rather than keep feeding the agent data to try to make it intelligent enough to make those determinations, it was simpler and more efficient for the agent to create a proposed stakeholder map and hand it over to a human who could make changes and explain why those changes were necessary.

Ultimately, Thakrar said the agent still saved human team members time because the stakeholder map was usually pretty close, and the corrections also helped the model grow smarter by adding richer context.

Specialization

Specialization is transitioning a process from testing on a frontier model to production on a much narrower, smaller model. Once you’ve proven that an agent can do a job well, you want to stop paying master-craftsman rates to keep doing that one job well.

Specialization is all about capturing your subject matter experts’ best judgement and pattern recognition to build an open-weight, open source, trained, and fine-tuned model that can be deployed in your own data center.

“The true enterprise bet is to keep that orchestration layer, which is your IP and knowledge, in house,” Thakrar said. “You don’t want to host that on someone else’s model. The goal of everyone in enterprise should be to run, train, and host their own models.”

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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Four months of Claude Code — that’s all it took for Uber to burn through its entire annual budget for AI. Token after token, engineers embraced the platform with few control mechanisms tying costs to outcomes. The result was a budget runaway and a clear case study in how limited oversight snowballs into an AI blowout.

This is a phenomenon I like to call “shadow tokens” — AI credits paid for by the company but largely invisible to decision-makers. Too many engineers have the final say over how much they consume and, therefore, what it costs. This all-you-can-eat attitude is part of the reason why Microsoft is reportedly winding down many internal licenses across key engineering teams and why one in five organizations is missing its AI spend forecast by more than 50%.

And the trend is only accelerating. By 2028, Gartner predicts that AI coding costs (driven by this kind of ungoverned consumption) will be as much per developer as the salary companies pay that person.

LLMs and agents introduce a new class of variable cost that scales with behavior rather than headcount, putting enterprises on the hook for tools that balloon with workload. I don’t see this as enterprises overspending because they’re reckless — it’s down to a lack of managerial oversight, budget alignment that demands a proven return on investment, and engineer education on how much is too much.

Going forward, CIOs need to thread the AI needle between governance that encourages transparency and reasonable spend without stifling innovation.

When shadow tokens result in real costs

The issue is that AI isn’t a traditional line item. Previously, enterprise leaders onboarded software-as-a-service (SaaS) with a good idea of the total cost. An allocated software seat or annual contract was a known quantity. The cloud added some variation (with fluctuations depending on hosting size), but instances were still modelable. AI flips this status quo on its head — the unit of consumption is behavior and the cost is exponential.

And these specifics aren’t immediately apparent at pilot. Tools can appear inexpensive in controlled experiments yet unpredictably scale depending on session length, context window size, model selection and whether agents run in parallel. This is the fallacy of the $20-per-seat enterprise plan — tokens are charged separately at API rates with no ceiling. The final dollar value of any session is set by factors that finance can’t always model in advance, particularly when these decisions usually rest with the engineers themselves.

According to Deloitte, only 21% of organizations deploying agents have a mature governance model, a real concern because they’re token-eating machines. This is what was happening at Uber — Claude Code in agentic mode was autonomously reading codebases, planning changes across dozens of files and opening pull requests. Each step quickly adds up, with Anthropic’s own documentation noting that agents consume approximately seven times as many tokens as standard sessions.

This is shadow IT and shadow AI, evolved. This time, however, many leaders approved the tool in question without guardrails governing consumption. AI hype adds fuel to the fire and normalizes long sessions. Uber’s CTO, for example, described a company-wide shift toward “agentic software engineering” with employees “who are quietly experimenting, quietly shipping and quietly pushing things forward”. This is an exciting way to test the limits of what’s possible, certainly, but it’s also a position that goes a long way to explaining how the company spent its annual AI budget by April.

Shifting the culture from usage to yield

Engineers haven’t done anything wrong here. In fact, they’re adopting and experimenting as instructed, with Uber creating leaderboards and ranking users by token consumption. More use led to a better ranking, reflecting a culture that lauds new ways of doing things. This behavior is known as “tokenmaxxing,” and its principal knock-on effect is shadow tokens — quantity-over-quality processes that leaders struggle to control until they’re fully realized in the budget. Of course, if management treats adoption metrics as performance metrics, then engineers can’t be blamed for using more tokens. The tension is that the teams driving adoption aren’t the ones managing spend.

None of this is meant to dismiss AI’s productivity possibilities and potential return on investment. Developers save 3.6 hours per week, achieve 60% higher pull request throughput and cut onboarding time in half with automation. Meanwhile, Uber shared that roughly 11% of live backend updates were written by agents with no human in the loop. However, these wins aren’t the problem — it’s that too many teams aren’t connecting input to output. I’ve spoken to admins who discovered their token spend had tripled in a single quarter after using heavier models or accidentally doubling up on agentic applications. Nobody knew until the financial damage was done.

Automation needs to happen sustainably with an eye on the bottom line. In my view, a much better metric for achieving this is AI yield — the measurable business or engineering output generated per dollar spent on tokens. Otherwise, without a feedback loop, even genuinely productive teams are flying blind.

Stopping token waste before an AI blowout

Creating that throughline between AI investment and token consumption starts with established financial metrics. This is possible via maximum spend limits (dictated by spend tagging, workload tiering and cost-per-output benchmarks) per team or project. Then, any additional allocation requires approval, closing the loop between the engineers spending the tokens and the leaders paying for them. AI isn’t cheap and teams should demonstrate a bang for their buck.

This is something we do with our engineering team at Hexnode. Resource allocation for Claude Code and Cursor is tied directly to ROI rather than letting consumption run open-ended. Given the pay-as-you-go nature of these tools, a firm usage limit per team offers simple but essential control.

Similarly, there’s room to apply some of the governance principles IT uses for device management. Things like policy enforcement, role-based access, real-time monitoring and automated alerts can flag usage behavior in advance. Uncovering such insights at the token layer works to identify power users and prevent excessive spending.

We also need to encourage cultures that praise outputs that actually achieve efficiency. AI applications that result in shipping faster, reducing rework and cutting review cycles are gains that should be celebrated. If your company hosts leaderboards, frame unnecessary token burn as wasteful rather than valuable. The organizations creating healthier consumption habits work with their engineers to understand not just how to use AI, but what responsible use looks like and what it costs.

This is a conversation teams need to have now. Anthropic just ended flat-rate pricing for programmatic workloads from June 15. Now, agents, continuous integration pipelines and automated workflows draw from a dedicated monthly credit pool billed separately from the subscription. Once that pool is exhausted, agent tasks either stop entirely or overflow to extra billing. Work can either get very expensive or grind to a halt for teams that aren’t prepared.

Getting a grip on shadow tokens means better rules and tools connecting spend to outcomes. Only by building the financial and cultural infrastructure that encourages sustainable adoption can leaders see what they’re spending, connect it to what they’re getting and course-correct before the costs become a crisis. Ultimately, shadow tokens are only invisible if we choose not to look.

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In August 2025, 126 malicious packages landed in the npm registry. Even after the community caught the initial wave, 80 of these hidden backdoors remained actively listed.

That was enough. Over 86,000 downloads. Malicious code in PhantomRaven, packages running in the production systems of Fortune 500 companies worldwide. And throughout the entire window, not a single EDR/XDR alert.

This happened because the attack surface has expanded to a layer EDR/XDR was never designed to see: VS Code extensions, local MCP servers, and rogue AI coding assistants that inherit your engineers’ valid credentials to steal data at machine speed.

To eliminate this structural vulnerability, Palo Alto Networks acquired Koi, an AI-native developer security product engineered for proactive, precision enforcement. Below we compiled a 2026 CISO checklist you can use to audit your environment and see how Koi automates each defense from day one.

#1. Gain real-time visibility into shadow AI & extensions

Your existing asset management tracks binaries and installers, but it cannot see local VS Code extensions, MCP servers, or ad-hoc Python scripts running on developer endpoints. This visibility gap was recently exposed by the MaliciousCorgi campaign, where two marketplace extensions with 1.5 million combined installs silently harvested every file a developer opened. Neither triggered any detection because they were not binaries, not executables, not anything your inventory was built to flag. To counter this, Koi closes the gap by analyzing what extensions actually do after installation, exposing hidden data-harvesting channels running inside your active workspace.

#2. Distinguish between human and autonomous agent behavior 

When a rogue AI agent exfiltrates your proprietary source code, it uses a developer’s valid credentials during normal working hours, making the session look entirely legitimate to standard XDR baselines. Moving beyond static permission lists, Koi deploys behavioral profiling within the workspace runtime. By actively intercepting unauthenticated background tasks and blocking unauthorized file-system reads, it stops automated data exfiltration in real time.

#3. Establish guardrails for automated package updates on endpoints

Developers prioritize speed, often allowing software packages to auto-update on their endpoints the moment a new version appears. Attackers weaponize this supply chain vulnerability, as seen in the May 2026 Team PCP attack where 3,800 GitHub repositories were compromised in just 36 minutes via poisoned auto-updates. Securing agentic endpoints against these rapid breaches requires behavior-based inspection within the active workspace context. Koi operates at this layer by providing safe deployment buffers that automate version cooldowns, blocking bleeding-edge updates until they are vetted. By continuously auditing process creation within the IDE runtime, Koi instantly drops unauthorized remote connections before malicious payloads can exfiltrate credentials from the endpoint.  

#4. Enforce principle of least privilege for AI agents

AI coding assistants inherit the privileges of whoever deployed them. In practice, that means read access to production databases, write access to core repositories, and access to every secret in environment files and configuration directories. To restrict this excessive access, Koi applies dynamic sandboxing directly to AI agent processes at the kernel level. It enforces a strict zero-trust boundary that segregates sensitive workspace vectors, preventing agents from pulling data outside their approved scope without interrupting developer workflows.

#5. Maintain continuous endpoint posture management

Signature-based scanning only stops known threats. Sophisticated repository attacks often arrive as functional, high-rated software that carries no known bad signature. Koi’s research into the DarkSpectre campaign found eight browser extensions, all carrying “featured” badges from Google and Microsoft, installed by over 8 million users, silently harvesting every conversation from ChatGPT, Claude, and Gemini in the background. Koi addresses this by operating upstream: scanning marketplace listings every hour, using LLM-driven code analysis to compare what software promises against what its code does, sandboxing it, and scoring the risk before it ever reaches the endpoint.

Summary

Securing the modern enterprise is no longer about patching individual gaps. As AI agents redefine the workforce, Agentic Endpoint Security (AES) is now a strategic imperative for every CISO. By establishing a mandatory control plane for the AI-native workspace, AES ensures that your organization can scale engineering velocity without ever compromising enterprise integrity. 

Ready to secure the future of your software stack? See how Koi Agentic Endpoint Security delivers complete visibility, risk scoring, and real-time prevention across every endpoint in your enterprise.