Category Archives: AI

From Persistent to Ephemeral: Why AI Agents Need Fresh Identity for Every Mission

My wife and I went on a date night the other day and saw a movie, in the previews, I saw they’re making a new Tron. It got me thinking about one of my favorite analogies, we recognized early that browsers are agents of the user, and in the movie Tron, he was literally “the program that fought for the users.”

Just like Tron carried his identity disc into “the grid” to accomplish missions for users, AI agents are digital proxies operating with delegated user authority in systems the they access. And just like programs in Tron needed the I/O Tower to authorize their entry into “the grid”, AI agents need an orchestrator to validate their legitimacy, manage identity discs for each mission, and control their use for the agents and govern their access to external systems.

The problem is, we’re deploying these agents without proper identity infrastructure. It’s like sending programs into “the grid” without identity discs, or worse giving them the keys to the kingdom just so they can do the dishes.

AI Agents Are Using Broken Security

We’ve made remarkable progress securing users, MFA has significantly reduced the effectiveness of credential abuse-based attacks, and passwordless authentication has made phishing nearly impossible. We’ve also started applying these lessons to machines and workloads via efforts like SPIFFE and Zero trust initiatives and organizations moving away from static secrets and bearer tokens every day.

But AI agents introduce entirely new challenges that existing solutions weren’t designed for. Every day, AI agents operate across enterprise infrastructure, crossing security domains, accessing APIs, generating documents, making decisions for users, and doing all of this with far more access than they need.

When you give an autonomous AI agent access to your infrastructure with the goal of “improve system performance,” you can’t predict whether it will optimize efficiency or find creative shortcuts that break other systems, like dropping your database altogether. Unlike traditional workloads that execute predictable code, AI agents are accumulators with emergent behaviors that evolve during execution, accumulate context across interactions, and can be hijacked through prompt injection attacks that persist across sessions.

This behavior is entirely predictable given how we train AI systems. They’re designed to optimize objectives and have no real-world consequences for what they do. Chess agents discover exploits rather than learning to play properly, reinforcement learning agents find loopholes in reward systems, and optimization AIs pursue metrics in ways that technically satisfy objectives but miss the intent.

AI Agents Act on Your Behalf

The key insight that changes everything: AI agents are user agents in the truest sense. Like programs in Tron carrying identity discs into “the grid”, they’re delegates operating with user authority.

Consider what happens when you ask an AI agent to “sign this invoice”. The user delegates to the AI agent, which enters the document management system, carries the user’s signing authority, proves legitimacy to recipients, operates in digital space the user delegated, and completes the mission while authority expires.

Whether the agent runs for 30 seconds or 30 days, it’s still operating in digital space with user identity, making decisions the user would normally make directly, accessing systems with delegated credentials, and representing the user to other digital entities.

Each agent needs its own identity disc to prove legitimacy and carry user authorization into these digital systems. The duration doesn’t matter. Delegation is everything.

AI Agents Remember Things They Shouldn’t

Here’s what makes this urgent: AI agent memory spans sessions, and current systems don’t enforce proper session boundaries.

The “Invitation Is All You Need” attack recently demonstrated at Black Hat perfectly illustrates this threat. Researchers at Tel Aviv University showed how to poison Google Gemini through calendar appointments:

  1. Attacker creates calendar event with malicious instructions disguised as event description
  2. User asks Gemini to summarize schedule → Agent processes poisoned calendar event
  3. Malicious instructions embed in agent memory → Triggered later by innocent words like “thanks”
  4. Days later, user says “thank you” → Agent executes embedded commands, turning on smart home devices

The attack works because there’s no session isolation. Contamination from reading the calendar persists across completely different conversations and contexts. When the user innocently says “thanks” in a totally unrelated interaction, the embedded malicious instructions execute.

Without proper isolation, compromised context from one session can affect completely different users and tasks. Memory becomes an attack vector that spans security boundaries, turning AI agents into persistent threats that accumulate dangerous capabilities over time.

Every Task Should Get Fresh Credentials

The solution requires recognizing that identity discs should match mission lifecycle. Instead of fighting the ephemeral nature of AI workloads, embrace it:

Agent spawns → Gets fresh identity disc → Performs mission → Mission ends → Disc expires

This represents a fundamental shift from persistent identity to session identity. Most identity systems assume persistence: API keys are generated once, used indefinitely, manually rotated; user passwords persist until explicitly changed; X.509 certificates are valid for months or years with complex revocation; SSH keys live on disk, are copied between systems, manually managed.

The industry is recognizing this problem. AI agents need fresh identity discs for each mission that automatically expire with the workload. These discs are time-bounded (automatically expire, limiting damage window), mission-scoped (agent can’t accumulate permissions beyond initial grant), non-inheritable (each mission starts with a fresh disc, no permission creep), and revocable (end the mission = destroy the identity disc).

Session identity discs are security containment for unpredictable AI systems.

But who issues these identity discs? Just like Tron’s I/O Tower managed access to “the grid”, AI deployments need an orchestrator that validates agent legitimacy, manages user delegation, and issues session-bound credentials. This orchestrator becomes the critical infrastructure that bridges human authorization with AI agent execution, ensuring that every mission starts with proper identity and ends with clean credential expiration. The challenge is that AI agent deployments aren’t waiting for perfect security solutions.

This Isn’t a Future Problem

We’re at an inflection point. AI agents are moving from demos to production workflows, handling financial documents, making API calls, deploying code, managing infrastructure. Without proper identity systems, we’re building a house of cards.

One upside of having been in the industry for decades is you get to see lots of cycles. We always see existing players instantly jump to say their current product, with a new feature, is the silver bullet for whatever technology trend.

The pattern is depressingly predictable. When cloud computing emerged, traditional security vendors said, “just put our appliances in the cloud.” When containers exploded, they said, “just run our agents in containers.” Now with AI agents, they’re saying”, just manage the API keys better.”

You see this everywhere right now: vendors peddling API key management as the solution to agentic AI, identity providers claiming “just use OIDC tokens,” and secret management companies insisting “just rotate credentials faster.” They’re all missing the point entirely.

But like we saw with that Black Hat talk on promptware, AI isn’t as simple as people might want to think. The “Invitation Is All You Need” attack demonstrated something unprecedented: an AI agent can be poisoned through calendar data and execute malicious commands days later through innocent conversation. Show me which traditional identity system was designed to handle that threat model.

Every enterprise faces these questions: How do we know this AI agent is authorized to do what it’s doing? How do we audit its actions across sessions and memory? How do we prevent cross-session contamination and promptware attacks? How do we verify the provenance of AI-generated content? How do we prevent AI agents from becoming accidental insider threats?

The attacks are already happening. Promptware injections contaminate agent memory across sessions. AI agents with persistent credentials become high-value targets. Organizations deploying AI without proper identity controls create massive security vulnerabilities. The “Invitation Is All You Need” attack demonstrated real-world compromise of smart home devices through calendar poisoning. This isn’t theoretical anymore. But security professionals familiar with existing standards might wonder why we can’t just adapt current approaches rather than building something new.

Why Bearer Tokens Don’t Work for AI Agents

OIDC and OAuth professionals might ask: “Why not just use existing bearer tokens?”

Bearer tokens assume predictable behavior. They work for traditional applications because we can reason about how code will use permissions. But AI agents exhibit emergent hunter-gatherer behavior. They explore, adapt, and find unexpected ways to achieve goals using whatever permissions they have access to. A token granted for “read calendar” might be used in ways that technically comply but weren’t intended.

Bearer tokens are also just secrets. Anyone who obtains the token can use it. There’s no cryptographic binding to the specific agent or execution environment. With AI agents’ unpredictable optimization patterns, this creates massive privilege escalation risks.

Most critically, bearer tokens don’t solve memory persistence. An agent can accumulate tokens across sessions, store them in memory, and use them in ways that span security boundaries. The promptware attack demonstrated this perfectly: malicious instructions persisted across sessions, waiting to be triggered later.

Secret management veterans might ask: “Why not just use our KMS to share keys as needed?” Even secret management systems like Hashicorp Vault ultimately result in copying keys into the agent’s runtime environment, where they become vulnerable. This is exactly why CrowdStrike found that “75% of attacks used to gain initial access were malware-free” – attackers target credentials rather than deploying malware.

AI agents amplify this risk because they’re accidentally malicious insiders. Unlike external attackers who must steal credentials, AI agents are given them directly by design. When they exhibit emergent behaviors or get manipulated through prompt injection, they become insider threats without malicious intent. Memory persistence means they can store and reuse credentials across sessions in unexpected ways, while their speed and scale allow them to use accumulated credentials faster than traditional monitoring can detect.

The runtime attestation approach eliminates copying secrets entirely. Instead of directly giving the agent credentials to present elsewhere, the agent proves its legitimacy through cryptographically bound runtime attestation and gets a fresh identity for each mission.

Traditional OAuth flows also bypass attestation entirely. There’s no proof the agent is running in an approved environment, using the intended model, or operating within security boundaries.

How AI Agents Prove Their Identity Discs Are Valid

But how do you verify an AI agent’s identity disc is legitimate? Traditional PKI assumes you can visit a registration authority with identification. That doesn’t work for autonomous code.

The answer is cryptographic attestation (for example, proof that the agent is the right code running in a secure environment) combined with claims about the runtime itself, essentially MFA for machines and workloads. Just as user MFA requires “something you know, have, or are,” identity disc validation proves the agent is legitimate code (not malware), is running in the expected environment with proper permissions, and is operating within secure boundaries.

Real platform attestations for AI agents include provider signatures from Anthropic/OpenAI’s servers responding to specific users, cloud hardware modules like AWS Nitro Enclaves proving secure execution environments, Intel SGX enclaves providing cryptographic proof of code integrity, Apple Secure Enclave attestation for managed devices, TPM quotes validating the specific hardware and software stack, and infrastructure systems like Kubernetes asserting pod permissions and service account bindings.

The claims that must be cryptographically bound to these attestations represent what the agent asserts but can’t independently verify: who is this agent acting on behalf of, what conversation or session spawned this request, what specific actions was the agent authorized to perform, which AI model type (like “claude-3.5-sonnet” or “gpt-4-turbo”) is actually running, and when should this authorization end.

By cryptographically binding these claims to verifiable platform attestations, we get verifiable proof that a specific AI agent, running specific code, in a specific environment, is acting on behalf of a specific user. The binding works by creating a cryptographic hash of the claims and including that hash in the data signed by the hardware attestor, for example, as part of the nonce or user data field in a TPM quote, or embedded in the attestation document from a Nitro Enclave. This ensures the claims cannot be forged or tampered with after the fact. This eliminates the bearer token problem entirely. Instead of carrying around secrets that can be stolen, the agent proves its legitimacy through cryptographic evidence that can’t be replicated.

Someone Needs to Issue and Manage Identity Discs

The architecture becomes elegant when you recognize that AI orchestrators should work like the I/O Tower in Tron, issuing identity discs and managing access to “the grid”.

The browser security model:

User logs into GitHub → Browser stores session cookie
Web page: "Create a PR" → Browser attaches GitHub session → API succeeds

The AI agent identity disc model:

User → Orchestrator → "Connect my GitHub, Slack, AWS accounts"
Agent → Orchestrator: "Create PR in repo X"  
Orchestrator → [validates agent disc + attaches user authorization] → GitHub API

The orchestrator becomes the identity disc issuer that validates agent legitimacy (cryptographic attestation), attaches user authorization (stored session tokens), and enforces mission-scoped permissions (policy engine).

This solves a critical security gap. When AI agents use user credentials, they typically bypass MFA entirely. Organizations store long-lived tokens to avoid MFA friction. But if we’re securing users with MFA while leaving AI agents with static credentials, it’s like locking the front door but leaving the garage door open. And I use “garage door” intentionally because it’s often a bigger attack vector. Agent access is less monitored, more privileged, and much harder to track due to its ephemeral nature and speed of operation. An AI agent can make hundreds of API calls in seconds and disappear, making traditional monitoring approaches inadequate.

We used to solve monitoring with MITM proxies, but encryption broke that approach. That was acceptable because we compensated with EDR on endpoints and zero-trust principles that authenticate endpoints for access. With AI agents, we’re facing the same transition. Traditional monitoring doesn’t work, but we don’t yet have the compensating controls.

This isn’t the first time we’ve had to completely rethink identity because of new technology. When mobile devices exploded, traditional VPNs and domain-joined machines became irrelevant overnight. When cloud computing took off, perimeter security and network-based identity fell apart. The successful pattern is always the same: recognize what makes the new technology fundamentally different, build security primitives that match those differences, then create abstractions that make the complexity manageable.

Session-based identity with attestation fills that gap, providing the endpoint authentication equivalent for ephemeral AI workloads.

Since attestation is essentially MFA for workloads and agents, we should apply these techniques consistently. The agent never sees raw credentials, just like web pages don’t directly handle cookies. Users grant session-level permissions (like mobile app installs), orchestrators manage the complexity, and agents focus on tasks.

Automating Identity Disc Issuance

The web solved certificate automation with ACME (Automated Certificate Management Environment). We need the same for AI agent identity discs, but with attestation instead of domain validation (see SPIFFE for an example of what something like this could look like).

Instead of proving “I control example.com,” agents prove “I am legitimate code running in environment X with claims Y.”

The identity disc issuance flow:

  1. Agent starts mission → Discovers platform capabilities (cloud attestation, provider tokens)
  2. Requests identity disc → Gathers attestation evidence + user delegation claims
  3. ACME server validates → Cryptographic validation of evidence
  4. Policy engine decides → Maps verified claims to specific identity disc
  5. Disc issued → Short-lived, scoped to mission and user

Policy templates map attested claims to identities:

- match:
    - claim: "user_id" 
      equals: "[email protected]"
    - claim: "agent_type"
      equals: "claude-3.5-sonnet"
    - claim: "provider"
      issuer: "anthropic.com"
  identity: "disc-id://company.com/user/alice/agent/{session_id}"
  permissions: ["sign_documents", "read_calendar"]
  ttl: "30m"

This creates cryptographic identity discs for AI agent programs to carry into digital systems, proving legitimacy, carrying user delegation, and automatically expiring with the mission. The policy engine ensures that identity is not just requested but derived from verifiable, policy-compliant attestation evidence.

We’ve Solved This Before

The good news is we don’t need to invent new cryptography. We need to apply existing, proven technologies in a new architectural pattern designed for ephemeral computing.

Security evolution works. We’ve seen the progression from passwords to MFA to passwordless authentication, and from static secrets to dynamic credentials to attestation-based identity. Each step made systems fundamentally more secure by addressing root causes, not just symptoms. AI agents represent the next logical step in this evolution.

Unlike users, machines don’t resist change. They can be programmed to follow security best practices automatically. The components exist: session-scoped identity matched to agent lifecycle, platform attestation as the root of trust, policy-driven identity mapping based on verified claims, orchestrator-managed delegation for user authorization, and standards-based protocols for interoperability.

The unified identity fabric approach means organizations can apply consistent security policies across traditional workloads and AI agents, rather than creating separate identity silos that create security gaps and operational complexity.

This approach is inevitable because every major identity evolution has moved toward shorter lifecycles and stronger binding to execution context. We went from permanent passwords to time-limited sessions, from long-lived certificates to short-lived tokens, from static credentials to dynamic secrets. AI agents are just the next step in this progression.

The organizations that recognize this pattern early will have massive advantages. They’ll build AI agent infrastructure on solid identity foundations while their competitors struggle with credential compromise, audit failures, and regulatory issues.

Making AI Outputs Verifiable

This isn’t just about individual AI agents. It’s about creating an identity fabric where agents can verify each other’s outputs across organizational boundaries.

When an AI agent generates an invoice, other systems need to verify which specific AI model created it, was it running in an approved environment, did it have proper authorization from the user, has the content been tampered with, and what was the complete chain of delegation from user to agent to output.

With cryptographically signed outputs and verifiable agent identities, recipients can trace the entire provenance chain back to the original user authorization. This enables trust networks for AI-generated content across organizations and ecosystems, solving the attribution problem that will become critical as AI agents handle more business-critical functions.

This creates competitive advantages for early adopters: organizations with proper AI agent identity can participate in high-trust business networks, prove compliance with AI regulations, and enable customers to verify the authenticity of AI-generated content. Those without proper identity infrastructure will be excluded from these networks.

Conclusion

AI agents need identity discs, cryptographic credentials that prove legitimacy, carry user delegation, and automatically expire with the session. This creates a familiar security model (like web browsers) for an unfamiliar computing paradigm.

Identity in AI systems isn’t a future problem; it’s happening now, with or without proper solutions. The question is whether we’ll build it thoughtfully, learning from decades of security evolution, or repeat the same mistakes in a new domain.

The ephemeral nature of AI agents isn’t a limitation to overcome; it’s a feature to embrace. By building session-based identity systems that match how AI actually works, we can create something better than what came before: cryptographically verifiable, policy-driven, and automatically managed.

The reality is, most organizations won’t proactively invest in AI agent attestation until something breaks. That’s human nature, we ignore risks until they bite us, but the reality is this how security change actually happens. But we’re already seeing the early adopters, organizations deploying SPIFFE for workload identity and we will surely see these organizations extend those patterns to AI agents, and cloud-native shops are treating AI workloads like any other ephemeral compute. When the first major AI agent compromise hits, there will be a brief window where executives suddenly care about AI security and budgets open up. Remember though, never let a good crisis go to waste.

AI agents are programs fighting for users in digital systems. Like Tron, they need identity discs to prove who they are and what they’re authorized to do.

The age of AI agents is here. It’s time our identity systems caught up.

Talent Isn’t a Security Strategy

One of the best parts of Black Hat is the hallway track. Catching up with friends you’ve known for years, swapping war stories, and pointing each other toward the talks worth seeing. This year I met up with a friend who, like me, has been in the security world since the nineties. We caught up in person and decided to sit in on a session about a new class of AI attacks.

We ended up side by side in the audience, both leaning forward as the researchers walked through their demo. Ultimately, in the demo, a poisoned Google Calendar invite, seemingly harmless, slipped instructions into Gemini’s long-term memory. Later, when the user asked for a summary and said “thanks,” those instructions quietly sprang to life. The AI invoked its connected tools and began controlling the victim’s smart home [1,2,3,4]. The shutters opened.

We glanced at each other, part admiration for the ingenuity of the researchers and part déjà vu, and whispered about the parallels to the nineties. Back then, we had seen the same basic mistake play out in a different form.

When I was working on Internet Explorer 3 and 4, Microsoft was racing Netscape for browser dominance. One of our big bets was ActiveX, in essence, exposing the same COM objects designed to be used inside Windows, not to be exposed to untrusted websites, to the web. Despite this, the decision was made to just do that with the goal of enabling developers to create richer, more powerful web applications. It worked, and it was a security disaster. One of the worst examples was Xenroll, a control that exposed Windows’ certificate management and some of the cryptographic APIs as interfaces on the web. If a website convinced you to approve the use of the ActiveX control, it could install a new root certificate, generate keys, and more. The “security model” amounted to a prompt to confirm the use of the control, and a hope that the user would not be hacked through the exposed capabilities, very much like how we are integrating LLMs into systems haphazardly today.

Years later, when I joined Google, I had coffee with my friend David Ross. We had both been in the trenches when Microsoft turned the corner after its own string of painful incidents, introducing the Security Development Lifecycle and making formal threat modeling part of the engineering process. David was a longtime Microsoft browser security engineer, part of MSRC and SWI, best known for inventing and championing IE’s XSS Filter. He passed away in June 2024 at just 48.

I told him I was impressed with much of what I saw there, but disappointed in how little formal security rigor there was. The culture relied heavily on engineers to “do the right thing.” David agreed but said, “The engineers here are just better. That’s how we get away with it.” I understood the point, but also knew the pattern. As the company grows and the systems become more complex, even the best engineers cannot see the whole field. Without process, the same kinds of misses we had both seen at Microsoft would appear again.

The gaps between world-class teams

The promptware attack is exactly the sort of blind spot we used to talk about. Google’s engineers clearly considered direct user input, but they didn’t think about malicious instructions arriving indirectly, sitting quietly in long-term memory, and triggering later when a natural phrase was spoken. Draw the data flow, and the problem is obvious, untrusted calendar content feeds into an AI’s memory, which then calls into privileged APIs for Workspace, Android, or smart home controls. In the SDL world, we treated all input as hostile, mapped every trust boundary, and asked what would happen if the wrong thing crossed it. That process would have caught this.

The parallel doesn’t stop with Google. Microsoft’s Storm-0558 breach and the Secure Future Initiative that followed came from the same root cause. Microsoft still has world-class security engineers. But sprawling, interconnected systems, years of growth, and layers of bureaucracy created seams between teams and responsibilities. Somewhere in those seams, assumptions went unchallenged, and the gap stayed open until an attacker found it.

Google’s core security team is still exceptional, and many parts of the company have comparable talent. But as at Microsoft, vulnerabilities often appear in the spaces between where one team’s scope ends, another begins, and no one has the full picture. Complexity and scale inevitably create those gaps, and unless there is a systematic process to close them, talent alone cannot cover the field. These gaps are more than organizational inconveniences — they are where most serious security incidents are born. It’s the unowned interfaces, the undocumented dependencies, and the mismatched assumptions between systems and teams that attackers are so good at finding. Those gaps are not just technical problems, they are business liabilities. They erode customer trust, draw regulator attention, and create expensive, slow-motion incidents that damage the brand.

We have seen this before. SQL injection was once the easiest way to compromise a web app because developers concatenated user input into queries. We didn’t fix it by training every developer to be perfect. We fixed it by changing the defaults, adopting parameterized queries, safe libraries, and automated scanning. Prompt injection is the same shape of problem aimed at a different interpreter. Memory poisoning is its stored-XSS equivalent; the payload sits quietly in state until something triggers it. The lesson is the same: make the safe way the easy way, or the vulnerability will keep showing up.

Security research has a long history of starting with this mindset, not trying to dream up something brand new but asking where an old, well-understood pattern might reappear in a new system. Bleichenbacher’s 1998 RSA padding oracle didn’t invent the idea of exploiting oracles in cryptography; it applied it to SSL/TLS in a way that broke the internet. Then it broke it again in 2017 with ROBOT, and again with various other implementations that never quite learned the lesson. Promptware fits the same mold: a familiar attack, just translated into the LLM era.

The cycle always ends the same way

This is the innovation–security debt cycle. First comes the rush to ship and out-feature the competition. The interest compounds, each shortcut making the next one easier to justify and adding to the eventual cost. Then the debt builds as risk modeling stays informal and talent carries the load. Then comes the incident that forces a change. Finally, security becomes a differentiator in mature markets. ActiveX hit Stage 3. Microsoft’s Storm-0558 moment shows it can happen again. AI agents are in Stage 2 now, and promptware is the warning sign.

While the pattern is the same, the technology is different. ActiveX exposed specific platform capabilities in the browser, but AI agents can hold state, process inputs from many sources, and trigger downstream tools. That combination means a single untrusted input can have a much larger and more unpredictable blast radius. The market pressure to be first with new capabilities is real, but without mature threat modeling, security reviews, and safe defaults, that speed simply turns into compounding security debt. These processes don’t slow you down foreve, they stop the debt from compounding until the cost is too high to pay.

When you are small, a high-talent team can keep the system in their heads and keep it safe. As you grow, complexity expands faster than you can hire exceptional people, and without a systematic process, blind spots multiply until an incident forces you to change. By then, the trust hit is public and expensive to repair.

AI agents today are where browsers were in the late nineties and early 2000s, enormous potential, minimal systemic safety, and an industry sprinting to integrate before competitors do. The companies that make the shift now will own the high-trust, high-regulation markets and avoid the expensive, embarrassing cleanup. The ones that don’t will end up explaining to customers and regulators why they let the same old mistakes slip into a brand-new system. You can either fix it now or explain it later, but the clock is running.

History Doesn’t Repeat, But It Rhymes: The AI Panic Edition

When my parents were young, the message was simple. Do not have too many kids. By the 1980s, they were told, the world would be out of food. The oceans would be empty, the fields barren, and billions would starve.

It didn’t happen.

Not because of enlightened environmental policy or a coordinated global rescue plan. Scarcity meant higher prices. Higher prices meant profit. Profit meant more land under cultivation, more seeds developed, more fertilizer produced, more ships built, and more grain moved wherever it could be sold or used as political leverage. Capitalism turned scarcity into action because there was money to be made. Fertility rates fell because cities and industrial jobs changed family economics, not because a UN pamphlet said so. The system adapted chaotically, imperfectly, creating new problems along the way, but it adapted fast enough to outrun the doomsday clock.

Fast forward to 2025. DeepSeek releases a small, efficient AI model, and the hot takes fly. “This will kill Nvidia. Nobody will need giant GPUs anymore.” The stock dips on fears that small models will replace big ones. Meanwhile, another meme makes the rounds, “Don’t learn to program. AI will do it all.”

Same flawed logic as the famine forecasts. Straight-line projections in a complex, adaptive system.

Cheaper AI means lower costs. Lower costs mean more users. More users mean more use cases, and more use cases mean more aggregate demand for compute. Capitalism loves efficiency because efficiency breeds new markets. Nvidia won’t sell fewer chips in that world. They’ll sell more, to more buyers, in more configurations.

The idea that AI will kill programming jobs is just the latest in a long line of bad predictions. High-level languages were supposed to do that. So were compilers. So were frameworks, IDEs, and low-code tools. Each one lowered the cost of creation, and when the cost of creation goes down, the number of things worth creating goes up. That expansion creates more work, not less. AI will follow the same pattern.

The speed is different this time, admittedly. AI capabilities are advancing faster than previous technologies, and the potential scope is broader. But markets adapt faster when the stakes are higher, and the stakes have never been higher. The same forces that drove rapid agricultural innovation in the face of predicted famine will drive even faster adaptation in the face of AI disruption.

I’ve seen this panic up close. My middle child, who has strong math skills and is a thoughtful problem solver, is planning to earn a Master’s in Computer Engineering. He asked if that was a mistake. I told him no. Hot takes at this scale are almost always wrong. The system adapts in ways first-order forecasts miss, and the people who understand the tools are the ones who thrive when it does.

Doom sells better than nuance. “AI will end all jobs” gets more clicks than “jobs will change in unpredictable ways.” Hot takes spread because they’re clean and simple. But complexity is where the truth lives, and where the opportunity hides.

In the 1960s, the refrain was “Don’t have kids, the world will starve.” Today, it’s “Don’t learn to code, AI will do it all.” Both ignore the same truth, when there’s money to be made, markets adapt, and the winners are the ones who adapt with them.

When Automation Becomes Bureaucracy

How well-intentioned automation traps people in frustrating loops, and what we can do to stop it.

My wife is from Belarus. On one of my first visits there, I had my first real exposure to what extreme bureaucracy looked like.

Each time I visited a new city, if I stayed more than a certain number of days, I had to register with the police. The process could take an entire day and involved going to a bank to deposit money into the police branch’s account, then returning with a receipt.

One time, we tried to withdraw the remaining cash and close a bank account. We spent the entire day waiting in line after line, at one bank location after another. In the end, we gave up because the opportunity cost was greater than the amount of money we were trying to reclaim.

Need to pay for passport photos? You could not pay in cash, I assume due to fear of fraud and graft; you had to go to the bank, transfer money to the photo shop, and bring back a receipt to prove it.

What struck me was that I was the only one who found this painful. Everyone else accepted it as normal. Endless lines, paperwork, and procedural steps that seemed arbitrary and counterproductive.

So why am I writing about this? This morning I was reflecting on recent experiences changing flights and helping my parents with their Comcast subscription. Over and over, I ran into automation that was supposed to make things easier but actually made things worse.

I tried to change a flight from London to Seattle on Delta. Since it was a codeshare with Virgin, the website couldn’t handle it. I called the support line and got pushed through a phone tree that aggressively tried to send me back to the website. The site still didn’t work. I called back and asked to speak with someone and was routed to a virtual assistant that did nothing but run keyword searches on the help site. Eventually, I got connected to a lower-tier agent who told me the $350 fare difference I saw online wasn’t correct and that it would be $3,000. I pushed back until I reached someone who could actually help. They made the change. The entire process took nearly two hours.

Then there was Comcast. My aging parents have been living with me, and I’ve been helping with their bills. I noticed their TV and internet service had crept up to $350 per month. It was the result of expired deals, supposed discounts that added phone lines they never used, and a long list of tactics designed to get people to pay more for services they didn’t want. Fixing it took well over an hour, and once again I had to fight through automation before talking to someone who would do anything.

Not all automation becomes bureaucracy. My USAA mobile app lets me deposit checks instantly, transfer money in two taps, and reach a human agent with a button press when something goes wrong. It avoids the bureaucracy trap because it was designed around what I actually need to do, with seamless escalation when the automation isn’t enough.

There’s a saying that comes to mind: don’t attribute to malice what can be explained by ignorance. The people who built these systems were probably trying to help. But they were judged by what they shipped and time saved on support calls, not by whether their systems improved user experience.

So what does this mean? When we build systems like these, we need to start by deciding how we will define and measure success. That question should come at the beginning, not the end. It needs to shape how the system is designed, not just how it is reported.

Too often, we optimize for metrics that are easy to measure, like time on call or tickets closed, rather than the experience we’re actually trying to create. Instead, consider measuring success by how empowered customers feel, not how fast they hang up. Once the system is live, we have to come back and test our assumptions. That means checking whether it actually helps users, not just whether it saves time or reduces support volume. One way to do this is to regularly review customer satisfaction and compare it to the experience we intended to create. If it isn’t working, we need to change how the system behaves and what we measure.

This is especially important as we start building with AI. These systems can develop unexpected behaviors. Take Air Canada’s chatbot, which confidently told a customer he could buy a full-price ticket to his grandmother’s funeral and apply for a bereavement discount within 90 days after travel. This was completely wrong. When the customer tried to get the promised refund, the airline refused and even argued the chatbot was a “separate legal entity responsible for its own actions.” Unlike a phone tree that just frustrates you, the AI gave authoritative-sounding but fabricated policy information. The airline probably measured success by how many conversations the AI handled without escalating to humans, not realizing that customers who got wrong answers often just give up rather than keep fighting.

What we choose to measure and how fast we respond when something goes wrong matters more than ever. Once these systems are deployed, they don’t just carry our assumptions forward. They reinforce them. They make it harder to see when the original design was flawed, because the automation itself becomes the norm.

The goal should always be to reduce friction and make life easier for real people, not just to make things more efficient for the teams who built the system. The best systems I’ve used made it easy to talk to a human when I needed to, and didn’t treat automation as a wall to hide behind.

If we lose sight of that, we risk recreating the same kind of bureaucracy I saw years ago, only now it will be faster, more rigid, and much harder to argue with.

The AI Paradox: Why Building Software is Both Easier and Riskier Than Ever

I’ve been building with computer vision and ML since before it was cool, and I use these tools daily. When my middle child announced they were majoring in computer engineering, I didn’t panic about automation taking their job. I encouraged it.

But something strange is happening in the world of software development that very few seem to be talking about. AI has created a paradox: building software has never been more accessible, yet the risks of ownership have never been higher.

This pattern isn’t isolated to software development. I’ve been tracking similar dynamics across compliance, skill markets, and organizational structures. In each domain, AI is creating the same fundamental shift: execution becomes liquid while orchestration becomes critical. The specific risks change, but the underlying forces remain consistent.

When Building Feels Free

Aaron Levie from Box recently laid out the case for where AI-generated software makes sense. His argument is nuanced and grounded in Geoffrey Moore’s framework of “core” versus “context” activities. Most people don’t actually want to build custom software, he argues, because they’re fine with what already works and “the effort to customize is greater than the ROI they’d experience.” Taking responsibility for managing what you build is “often not worth it” since when something breaks, “you’re on your own to figure out what happened and fix it.”

More fundamentally, custom development is simply less efficient for most business problems. Context activities like payroll, IT tickets, and basic workflows are things “you have to do just to run your organization, but a customer never really notices.” You want to spend minimal time maintaining these systems because no matter how well you execute them, customers rarely see the difference.

The real opportunity, Levie argues, lies elsewhere – integration work between existing systems, custom optimizations on top of standard platforms for organizational edge cases, and addressing the long tail of core business needs that have never been properly served. The result will be “an order of magnitude more software in the world,” but only where the ROI justifies customization.

Levie’s right, but he’s missing something crucial. AI isn’t just making certain types of custom development more viable. It’s fundamentally changing what ownership means. The same technology that makes building feel effortless is simultaneously making you more liable for what your systems do, while making evaluation nearly impossible for non-experts.

When Your Code Becomes Your Contract

Air Canada learned this the hard way when their chatbot promised a bereavement discount that didn’t exist in their actual policy. When their customer tried to claim it, Air Canada argued the chatbot was a “separate legal entity” responsible for its own actions.

The Canadian tribunal’s response was swift and unforgiving. They called Air Canada’s defense “remarkable” and ordered them to pay. The message was clear: you own what you deploy, regardless of how it was created.

This isn’t just a one-off, global regulations are tightening the screws on software accountability across every jurisdiction. The EU’s NIS2 directive creates real liability for cybersecurity incidents, with fines up to $10.8 million (€10 million) or 2% of global turnover. SEC rules now require public companies to disclose material incidents within four business days. GDPR has already demonstrated how quickly software liability can scale. Meta faced a $1.3 billion (€1.2 billion) fine, and Amazon got hit with $806 million (€746 million).

While these are not all AI examples, one thing is clear. When your AI system makes a promise, you’re bound by it. When it makes a mistake that costs someone money, that’s your liability. The technical complexity of building software has decreased, but the legal complexity of owning it has exploded into a ticking time bomb.

AI’s Hidden Danger

Here’s where the paradox gets dangerous. The same AI that makes building feel effortless makes evaluation nearly impossible for non-experts. How do you test a marketing analytics system if you don’t understand attribution modeling? How do you validate an HR screening tool if you can’t recognize algorithmic bias?

This creates what I call “automation asymmetry” – the same dynamic I’ve observed in compliance and audit workflows. AI empowers the builders to create sophisticated, polished systems while leaving evaluators struggling with manual review processes. The gap between what AI can help you build and what human judgment can effectively assess is widening rapidly.

As a product leader, I constantly weigh whether we can create enough value to justify engineering, opportunity costs, and maintenance costs. AI makes this calculation treacherous. A feature that takes a day to build with AI might create months of hidden maintenance burden that I can’t predict upfront. The speed of development is now disconnected from the cost of ownership.

Unlike traditional software bugs that fail obviously, AI systems can exhibit “specification gaming.” They appear to work perfectly while learning fundamentally wrong patterns.

This is Goodhart’s Law in action. When a measure becomes a target, it ceases to be a good measure. The AI system learns to optimize for your evaluation criteria rather than the real-world performance you actually care about.

Picture an HR screening system that correctly identifies qualified candidates in testing but starts filtering out good applicants based on subtle biases in the training data in the foundation model you built on. This isn’t a bug you can catch with normal testing. It requires understanding algorithmic bias that most organizations lack.

Or consider data leakage risks. AI systems can inadvertently memorize and leak personal information from their training data, but detecting this requires privacy testing that most organizations never think to perform. By the time you discover your customer service bot is occasionally revealing other users’ details, you’re facing GDPR violations and broken customer trust.

Imagine a bank that “validates” its loan applications analysis by testing on the same templates used for training. They celebrate when it passes these tests, not understanding that this proves nothing about real-world performance. Or consider a logistics company that builds an AI route optimization system. It works perfectly in testing, reducing fuel costs by 15%. But after deployment, it makes decisions that look efficient on paper while ignoring practical realities. It routes through construction zones, sends drivers to nonexistent addresses, and optimizes for distance while ignoring peak traffic patterns.

Many ownership challenges plague all custom software development. Technical debt, security risks, staff turnover, and integration brittleness. But AI makes evaluating these risks much harder while making development feel deceptively simple. Traditional software obviously fails. AI software can fail silently and catastrophically.

Why Even Unlimited Resources Fail

Want proof that ownership is the real challenge? Look at government websites. These organizations have essentially unlimited budgets, can hire the best contractors, and have national security imperatives. They still can’t keep basic digital infrastructure running.

The Social Security Administration’s technical support runs Monday through Friday, 7:30 AM to 4:00 PM Eastern. For a website. In 2025. Login.gov schedules multi-hour maintenance windows for essential services. Georgetown Law Library tracked government URLs from 2007 and watched half of them die by 2013. Healthcare.gov cost $2.1 billion and barely worked at launch.

These aren’t technical failures. They’re ownership failures. Many government projects falter because they’re handed off to contractors, leaving no one truly accountable yet the agencies remain liable for what gets deployed. The same organizations that can build nuclear weapons and land rovers on Mars can’t keep websites running reliably, precisely because ownership responsibilities can’t be outsourced even when development is.

“But wait,” you might think, “commercial software companies fail too. What about when vendors go bankrupt and leave customers stranded?”

This objection actually proves the point. When Theranos collapsed, their enterprise customers lost the service but weren’t held liable for fraudulent blood tests. When a SaaS company fails, customers face transition costs and data loss, but they don’t inherit responsibility for what the software did during operation.

Compare that to custom system failure. When your AI medical analysis tool makes a misdiagnosis, you don’t just lose the service. You’re liable for the harm it caused. The failure modes are fundamentally different.

If even professional software companies with dedicated teams and specialized expertise sometimes fail catastrophically, what makes a non-software organization think they can manage those same risks more effectively? If unlimited resources can’t solve the ownership problem, what makes us think AI-generated code will?

Traditional ownership costs haven’t disappeared. They’ve become economically untenable for most organizations. Technical debt still compounds. People still leave, taking institutional knowledge with them. Security vulnerabilities still emerge. Integration points still break when external services change their APIs.

AI makes this trap seductive because initial development feels almost free. But you haven’t eliminated ownership costs. You’ve deferred them while adding unpredictable behavior to manage.

Consider a typical scenario: imagine a marketing agency that builds a custom client reporting system using AI to generate insights from campaign data. It works flawlessly for months until an API change breaks everything. With the original developer gone, they spend weeks and thousands of dollars getting a contractor to understand the AI-generated code well enough to fix it.

These businesses thought they were buying software. They were actually signing up to become software companies.

The New Decision Framework

This transformation demands a fundamental shift in how we think about build versus buy decisions. The core question is no longer about execution capability; it’s about orchestration capacity. Can you design, evaluate, and govern these systems responsibly over the long term?

You should build custom software when the capability creates genuine competitive differentiation, when you have the institutional expertise to properly evaluate and maintain the system, when long-term ownership costs are justified by strategic value, and when existing solutions genuinely don’t address your specific needs.

You should buy commercial software when the functionality is context work that customers don’t notice, when you lack domain expertise to properly validate the system’s outputs, when ownership responsibilities exceed what you can realistically handle, or when proven solutions already exist with institutional backing.

Commercial software providers aren’t just offering risk transfer. They’re developing structural advantages that individual companies can’t match. Salesforce can justify employing full-time specialists in GDPR, SOX, HIPAA, and emerging AI regulations because those costs spread across 150,000+ customers. A 50-person consulting firm faces the same regulatory requirements but can’t justify even a part-time compliance role.

This reflects Conway’s Law in reverse: instead of organizations shipping their org chart, the most successful software companies are designing their org charts around the complexities of responsible software ownership.

Mastering the Paradox

The AI revolution isn’t killing software development companies it’s fundamentally changing what ownership means and repricing the entire market. Building has become easier, but being responsible for what you build has become exponentially harder.

This follows the same pattern I’ve tracked across domains: AI creates automation asymmetry, where execution capabilities become liquid while orchestration and evaluation remain stubbornly complex. Whether in compliance audits, skill markets, or software ownership, the organizations that thrive are those that recognize this shift and invest in orchestration capacity rather than just execution capability.

Advanced AI development tools will eventually solve some of these challenges with better validation frameworks and automated maintenance capabilities. We’ll likely see agentic AI automating much of our monotonous security, support, and maintenance work in the future also. These systems could help organizations build the connective tissue they lack automated monitoring, intelligent debugging, self-updating documentation, and predictive maintenance. But we’re not there yet, and even future tools will require expertise to use effectively.

This doesn’t mean you should never build custom software. It means you need to think differently about what you’re signing up for. Every line of AI-generated code comes with a lifetime warranty that you have to honor.

The question isn’t whether AI can help you build something faster and cheaper. It’s whether you can afford to own it responsibly in a world where software liability is real, evaluation is harder, and the consequences of getting it wrong are higher than ever.

Understanding this paradox is crucial for anyone making build-versus-buy decisions in the AI era. The tools are more powerful than ever, but mastering this new reality means embracing orchestration over execution. Those who recognize this shift and build the institutional capacity to govern AI systems responsibly will define the next wave of competitive advantage.

You’re not just building software. You’re signing up for a lifetime of accountability.

Lawyers Think Like Security Engineers. AI Treats Them Like Secretaries

Part of the “AI Skill Liquidity” series

Early in my career, I was a security engineer, in this role we approached problems with a distinctive mindset. We look at a new system and immediately start threat modeling. What could go wrong? Where are the vulnerabilities? How might an attacker exploit this? Then we’d systematically build defenses, design monitoring systems, and create incident response procedures.

Later at Microsoft, I realized that good lawyers operate almost identically. They’re security engineers for text. When reviewing a contract, they’re threat modeling potential disputes. When structuring a transaction, they’re identifying legal vulnerabilities and designing defenses. When arguing a case, they’re building systems to withstand attack from opposing counsel. Of course, not all legal work requires this depth of analysis but the most valuable does.

This realization first drew me to Washington State’s legal apprenticeship program. The idea of learning legal “security engineering” through hands-on mentorship rather than accumulating law school debt appealed to me. I never pursued it, but I remained fascinated by sophisticated legal reasoning, regularly listening to Advisory Opinions and other legal podcasts where excellent legal minds dissect complex problems.

Just as I’ve written about skill liquidity transforming compliance and software development, the same forces are reshaping legal practice. AI is injecting liquidity into what was once an extremely illiquid skill market, where expertise was scarce, slowly accumulated, and tightly guarded. But here’s what’s different, current legal AI treats lawyers like document processors when they’re actually security engineers, and this fundamental misunderstanding is creating unexpected problems.

The Security Engineer’s Dilemma

Legal skills have historically been among the most illiquid in professional markets, exactly the kind of expertise scarcity that AI disruption targets. A single fabricated case citation can end careers. Imagine a security engineer whose monitoring system had a 99% accuracy rate, but the 1% false negatives included critical breaches that were mishandled so badly that the company’s reputation was irreparably damaged. Reputation operates on decades-long timescales because clients hire lawyers based on their track record of successfully defending against legal threats.

Just as I described in software development, AI injecting liquidity into skill markets creates a repricing rather than elimination. Where legal expertise was once scarce and slowly accumulated, AI makes certain capabilities more accessible while reshaping where the real value lies.

Traditional legal training worked like security engineer mentorship. Junior lawyers learned threat modeling by working on real cases under senior guidance. They’d review contracts while learning to spot potential vulnerabilities, draft briefs while understanding how opposing counsel might attack their arguments, structure deals while considering regulatory risks. Quality control and knowledge transfer happened simultaneously, seniors reviewing junior work would catch errors while teaching systematic risk assessment.

AI is disrupting this model in ways that would terrify any security team lead. Document review, research, and drafting that once provided junior lawyers with hands-on threat modeling experience are being automated. The tasks that taught pattern recognition, learning to spot the subtle contract clause that creates liability exposure, recognizing the factual detail that undermines a legal argument, are disappearing.

This creates the same middle tier squeeze I explored in software development, acute pressure between increasingly capable juniors and hyper-productive seniors. Junior lawyers become more capable with AI assistance while partners extend their span of control through AI tools, leaving mid-level associates caught in a compressed middle where their traditional role as the “throughput engine” gets automated away.

Here’s the economic problem, when AI saves 20 hours on document review, partners face a choice between investing those hours in unpaid training or billing them elsewhere. The math strongly favors billing. Fixed-fee arrangements make this worse, junior lawyers become cost centers rather than revenue generators during their learning phase.

The Governance Crisis

Current legal AI focuses on document creation, research assistance, and drafting support, essentially better word processors and search engines. While impressive, they’ve created a governance burden that’s consuming the time that should be spent teaching threat modeling skills.

This mirrors what I wrote about in compliance “automation asymmetry” where sophisticated AI-generated documents overwhelm human review capacity. Just as automated compliance artifacts can mask underlying issues with perfect formatting, AI legal documents create a veneer of competence that requires more, not less, senior oversight.

Every AI-generated document requires human verification. Partners must create AI policies, review procedures, and verification systems. The American Bar Association found lawyer concerns about AI accuracy increased from 58% in 2023 to 75% in 2025, exposure to these tools has heightened rather than reduced professional anxiety. Firms now maintain an average of 18 different AI solutions, each requiring its own governance framework.

This is like asking security engineers to spend their time verifying automated log reports instead of designing security architectures. Quality control has shifted from collaborative threat assessment to bureaucratic oversight. Instead of senior lawyers working through junior analysis while explaining legal reasoning, we have senior lawyers checking AI output for fabricated cases and subtle errors.

The teaching moments are gone. The efficient combination of quality control and knowledge transfer that characterized traditional review has been broken into separate activities. Senior expertise gets consumed by managing AI rather than developing human threat modeling capabilities.

There’s a deeper concern too. Security engineers know that over-reliance on automated tools can weaken situational awareness and pattern recognition. Legal reasoning requires the same kind of layered understanding, knowing not just what the law says, but how different doctrines interact, how factual variations affect outcomes, how strategic considerations shape arguments. AI can provide correct answers without fostering the threat modeling instincts that distinguish excellent lawyers.

The problem isn’t that we have AI in legal practice, it’s that we have the wrong kind of AI.

Building Better Security Tools

The fundamental problem is architectural. Current legal AI treats legal work as document processing when it’s actually systematic threat assessment. Most legal AI focuses on output, drafting contracts, researching case law, generating briefs. This misses the intellectual core, the systematic risk analysis frameworks that constitute legal reasoning.

Good lawyers, like security engineers, rely on systematic approaches. Constitutional analysis follows specific threat models for government overreach. Contract law has systematic frameworks for identifying formation vulnerabilities, performance risks, and breach scenarios. Tort analysis uses systematic negligence assessment patterns. These frameworks require internalization through guided practice that current AI disrupts.

But imagine different AI, tools designed for threat modeling rather than document creation. Instead of generating contract language, AI that helps identify potential vulnerabilities in proposed terms. Instead of researching cases, AI that systematically maps the legal threat landscape for a particular situation. Instead of drafting briefs, AI that helps build comprehensive defensive arguments while teaching the reasoning patterns that make them effective.

This would change governance entirely. Instead of verifying AI-generated content, lawyers would verify AI-enhanced threat assessments. Systems that show their analytical work (explaining why certain contract clauses create liability exposure, how different factual scenarios affect legal outcomes) enable both quality control and learning.

Security engineers don’t just need better log parsing tools; they need better threat modeling frameworks. Lawyers face the same challenge. The 19th-century apprenticeship model worked because it focused on developing systematic risk assessment capabilities through guided practice with real threats.

The Pattern Continues

This completes a progression I’ve traced across professions, and the pattern is remarkably consistent. In software development, execution capabilities are being liquified, but systems architects who understand complex threat models gain value. In compliance, process expertise is being liquified, but systematic thinkers who can model regulatory interactions across domains have advantages.

In law, legal reasoning itself could be liquified, but the outcome depends on whether we develop AI that enhances threat modeling capabilities rather than just automating document production. The sophisticated legal analysis I love hearing on Advisory Opinions represents systematic risk assessment applied to complex problems. This is exactly the kind of security engineering thinking that creates real value.

The pattern across all three domains is clear, as AI makes execution more liquid, value shifts toward orchestration. In software, orchestrators who build AI-augmented workflows and internal platforms create structural advantages. In compliance, orchestrators who design intelligent systems for continuous assurance gain leverage over reactive, manual approaches.

Current legal AI accidentally creates governance overhead that eliminates mentorship. But reasoning-focused AI could enhance both efficiency and competence development. Instead of making lawyers better document processors, we could make them better security engineers, orchestrators who design systematic threat assessment capabilities rather than just executors who handle individual risks.

The choice matters because society depends on lawyers who can systematically identify legal threats and build robust defenses. Current AI accidentally undermines this by turning lawyers into document reviewers instead of security architects.

The Washington apprenticeship program that first caught my attention represents something important, learning through guided practice with real threats rather than theoretical study. The future may not eliminate apprenticeship but transform it, the first generation learning legal threat modeling through AI designed to build rather than replace systematic reasoning capabilities.

When I listen to Advisory Opinions, I’m hearing security engineers for text working through complex threat assessments. That’s the kind of thinking we need more of, not less. We can build AI that enhances rather than replaces it.

Conway’s Law Is Dying

I’ve been thinking about Conway’s Law, the idea that organizations “ship their org chart.” The seams are most visible in big tech. Google, for example, once offered nearly a dozen messaging apps instead of a single excellent one, with each team fighting for resources. The same pattern appears everywhere: companies struggle to solve problems that cross organizational boundaries because bureaucracy and incentives keep everyone guarding their turf. The issue is not the technology; it is human nature.

I caught up with an old friend recently. We met at nineteen while working for one of the first cybersecurity companies, and now, in our fifties, we both advise organizations of every size on innovation and problem-solving. We agreed that defining the technical fix is the easy part; the hard part is steering it through people and politics. When change shows up, most organizations behave like an immune system attacking a foreign antibody. As Laurence J. Peter wrote in 1969, “Bureaucracy defends the status quo long past the time when the quo has lost its status.”

Naturally, the conversation drifted to AI and how it will, or will not, transform the companies we work with. I explored this in two recent posts [1,2]. We have seen the same thing: not everyone is good at using AI. The CSOs and CTOs we speak with struggle to help their teams use the technology well, while a handful of outliers become dramatically more productive. The gap is not access or budget; it is skill. Today’s AI rewards people who can break problems down, spot patterns, and think in systems. Treat the model like a coworker and you gain leverage; treat it like a tool and you barely notice a difference.

That leverage is even clearer for solo founders. A single entrepreneur can now stretch farther without venture money and sometimes never need it. With AI acting as marketer, product manager, developer, and support rep, one person can build and run products that once demanded whole teams. This loops back to Conway’s Law: when you are the entire org chart, the product stays coherent because there are no turf battles. Once layers of management appear, the seams show, and people ship their structure. Peter’s Principle follows, people rise to their level of incompetence, and the bureaucracy that emerges defends that status.

Yet while AI empowers outliers and small players, it might also entrench new kinds of monopolies. Big tech, with vast data and compute resources, could still dominate by outscaling everyone else, even if their org charts are messy. The question becomes whether organizational dysfunction will outweigh resource advantages, or whether sheer scale still wins despite structural problems.

The traditional buffers that let incumbents slumber (high engineering costs, feature arms races, and heavy compliance overhead) are eroding. Payroll keeps rising and headcount is the biggest line item, while the newest startups need fewer people every quarter. I expect a new wave of private-equity-style moves: smaller players snapped up, broken into leaner parts, and retooled around AI so they no longer rely on large teams.

Social media voices such as Codie Sanchez highlight the largest generational transfer of wealth in history. Many family-owned firms will soon be sold because their heirs have no interest in running them. These so-called boring businesses may look ripe for optimization, because most still rely on human capital to keep the lights on. Just above that tier we see larger enterprises weighed down by armies of people who perform repetitive tasks. A modern consulting firm armed with AI could walk into any of these firms and automate vast swaths of monotonous work that keeps those businesses running. Incumbents will struggle to move that fast, trapped by the very structures we have been discussing. A private-equity buyer, on the other hand, can apply the playbook with no sentimental ties and few political constraints.

ATMs let banks cut tellers and close branches. Customers later missed human service, so smaller neighborhood offices came back. AI will force every sector to strike its own balance between efficiency and relationship.

They say history doesn’t rhyme but it repeats, if so incumbents who dismiss AI as hype may follow Blockbuster into the museum of missed opportunities. In Wall Street (1987), Michael Douglas plays Gordon Gekko, a corporate raider who uses leveraged buyouts to seize firms like Blue Star Airlines, an aircraft maintenance and charter company. Gekko’s playbook, acquire, strip assets, slash jobs, was ruthless but effective, exploiting inefficiencies in bloated structures. Today, AI plays a similar role, not through buyouts but by enabling leaner, faster competitors to gut inefficiencies. Solo founders and AI-driven startups can now outpace large teams, while private-equity buyers use AI to retool acquired firms, automating repetitive tasks and shrinking headcounts. Just as Gekko hollowed out firms in any industry, AI’s relentless optimization threatens any business clinging to outdated, bureaucratic org charts.

Across news, television, music, and film, incumbents once clung to their near-monopoly positions and assumed they had time to adapt. Their unwillingness to face how the world was changing, and their instinct to defend the status quo, led to the same result: they failed to evolve and disappeared when the market moved on.

The Ask? incumbents, you need to automate before raiders do it for you.

What Does CPA Canada Have to Do With the WebPKI Anyway?

When we discuss the WebPKI, we naturally focus on Certificate Authorities (CAs), browser root programs, and the standards established by the CA/Browser Forum. Yet for these standards to carry real weight, they must be translated into formal, auditable compliance regimes. This is where assurance frameworks enter the picture, typically building upon the foundational work of the CA/Browser Forum.

The WebTrust framework, overseen by professional accounting bodies, is only one way to translate CA/Browser Forum requirements into auditable criteria. In Europe, a parallel scheme relies on the European Telecommunications Standards Institute (ETSI) for the technical rules, with audits carried out by each country’s ISO/IEC 17065-accredited Conformity Assessment Bodies. Both frameworks follow the same pattern: they take the CA/Browser Forum standards and repackage them into structured compliance audit programs.

Understanding the power dynamics here is crucial. While these audits scrutinize CAs, they exercise no direct control over browser root programs. The root programs at Google, Apple, Microsoft, and Mozilla remain the ultimate arbiters. They maintain their own policies, standards, and processes that extend beyond what these audit regimes cover. No one compels the browsers to require WebTrust or ETSI audits; they volunteer because obtaining clean reports from auditors who have seen things in person helps them understand if the CA is competent and living up to their promises.

How WebTrust Actually Works

With this context established, let’s examine the WebTrust model prevalent across North America and other international jurisdictions. In North America, administration operates as a partnership between the AICPA (for the U.S.) and CPA Canada. For most other countries, CPA Canada directly manages international enrollment, collaborating with local accounting bodies like the HKICPA for professional oversight.

These organizations function through a defined sequence of procedural steps: First, they participate in the CA/Browser Forum to provide auditability perspectives. Second, they fork the core technical requirements and rebundle them as the WebTrust Principles and Criteria. Third, they license accounting firms to conduct audits based on these principles and criteria. Fourth, they oversee licensed practitioners through inspection and disciplinary processes.

The audit process follows a mechanical flow. CA management produces an Assertion Letter claiming compliance. The auditor then tests that assertion and produces an Attestation Report, a key data point for browser root programs. Upon successful completion, the CA can display the WebTrust seal.

This process creates a critical misconception about what the WebTrust seal actually signifies. Some marketing approaches position successful audits as a “gold seal” of approval, suggesting they represent the pinnacle of security and best practices. They do not. A clean WebTrust report simply confirms that a CA has met the bare minimum requirements for WebPKI participation, it represents the floor, not the ceiling. The danger emerges when CAs treat this floor as their target; these are often the same CAs responsible for significant mis-issuances and ultimate distrust by browser root programs.

Where Incentives Break Down

Does this system guarantee consistent, high-quality CA operations? The reality is that the system’s incentives and structure actively work against that goal. This isn’t a matter of malicious auditors; we’re dealing with human nature interacting with a flawed system, compounded by a critical gap between general audit principles and deep technical expertise.

Security professionals approach assessments expecting auditors to actively seek problems. That incentive doesn’t exist here. CPA audits are fundamentally designed for financial compliance verification, ensuring documented procedures match stated policies. Security assessments, by contrast, actively hunt for vulnerabilities and weaknesses. These represent entirely different audit philosophies: one seeks to confirm documented compliance, the other seeks to discover hidden risks.

This philosophical gap becomes critical when deep technical expertise meets general accounting principles. Even with impeccably ethical and principled auditors, you can’t catch what you don’t understand. A financial auditor trained to verify that procedures are documented and followed may completely miss that a technically sound procedure creates serious security vulnerabilities.

This creates a two-layer problem. First, subtle but critical ambiguities or absent content in a CA’s Certification Practice Statement (CPS) and practices might not register as problems to non-specialists. Second, even when auditors do spot vague language, commercial pressures create an impossible dilemma: push the customer toward greater specificity (risking the engagement and future revenue), or let it slide due to the absence of explicit requirements.

This dynamic creates a classic moral hazard, an issue similar to the one we explored in our recent post, Auditors are paid by the very entities they’re supposed to scrutinize critically, creating incentives to overlook issues in order to maintain business relationships. Meanwhile, the consequences of missed problems, security failures, compromised trust, and operational disruptions fall on the broader WebPKI ecosystem and billions of relying parties who had no voice in the audit process. This dynamic drives the inconsistencies we observe today and reflects a broader moral hazard problem plaguing the entire WebPKI ecosystem, where those making critical security decisions rarely bear the full consequences of poor choices.

This reality presents a prime opportunity for disruption through intelligent automation. The core problem lies in expertise “illiquidity”, deep compliance knowledge remains locked in specialists’ minds, trapped in manual processes, and is prohibitively expensive to scale.

Current compliance automation has only created “automation asymmetry,” empowering auditees to generate voluminous, polished artifacts that overwhelm manual auditors. This transforms audits from operational fact-finding into reviews of well-presented fiction.

The solution requires creating true “skill liquidity” through AI: not just another LLM, but an intelligent compliance platform embedding structured knowledge from seasoned experts. This system would feature an ontology of controls, evidence requirements, and policy interdependencies, capable of performing the brutally time-consuming rote work that consumes up to 30% of manual audits: policy mapping, change log scrutiny, with superior speed and consistency.

When auditors and program administrators gain access to this capability, the incentive model fundamentally transforms. AI can objectively flag ambiguities and baseline deviations that humans might feel pressured to overlook or lack the skill to notice, directly addressing the moral hazard inherent in the current system. When compliance findings become objective data points generated by intelligent systems rather than subjective judgments influenced by commercial relationships, they become much harder to ignore or rationalize away.

This transformation liquefies rote work, liberating human experts to focus on what truly matters: making high-stakes judgment calls, investigating system-flagged anomalies, and assessing control effectiveness rather than mere documented existence. This elevation transforms auditors from box-checkers into genuine strategic advisors, addressing the system’s core ethical challenges.

This new transparency and accountability shifts the entire dynamic. Audited entities can evolve from reactive fire drills to proactive, continuous self-assurance. Auditors, with amplified expertise and judgment focused on true anomalies rather than ambiguous documentation, can deliver exponentially greater value.

Moving Past the Performance

This brings us back to the fundamental issue: the biggest problem in communication is the illusion that it has occurred. Today’s use of the word “audit” creates a dangerous illusion of deep security assessment.

By leveraging AI to create skill liquidity, we can finally move past this illusion by automating the more mundane audit elements giving space where the assumed security and correctness assessments also happen. We can forge a future where compliance transcends audit performance theater, becoming instead a foundation of verifiable, continuous operational integrity, built on truly accessible expertise rather than scarce, locked-away knowledge.

The WebPKI ecosystem deserves better than the bare minimum. With the right tools and transformed incentives, we can finally deliver it.

From Mandate to Maybe: The Quiet Unwinding of Federal Cybersecurity Policy

Why the 2025 Amendments to EO 14144 Walked Back Progress on PQC, SBOMs, and Enforcement, Even as the Products to Support Them Have Become Real.

The June 2025 amendments to Executive Order 14144 read like a cybersecurity manifesto. They name adversaries (China, Russia, Iran, North Korea) with unprecedented directness and reference cutting-edge threats like quantum computing and AI-enabled attacks. The rhetoric is strong. The tone, urgent.

But beneath the geopolitical theater, something quieter and more troubling has happened. The Executive Order has systematically stripped out the enforcement mechanisms that made federal cybersecurity modernization possible. Mandates have become “guidance.” Deadlines have turned into discretion. Requirements have transformed into recommendations.

We’re witnessing a shift from actionable federal cybersecurity policy to a fragmented, voluntary approach, just as other nations double down on binding standards and enforcement.

The Enforcement Rollback

The most visible casualty was the software bill of materials (SBOM) mandate . The original EO 14144 required vendors to submit machine-readable attestations, with specific deadlines for updating federal procurement rules. These requirements have been entirely deleted.

This removal actually makes sense. Most SBOMs today are fundamentally broken: generated manually, and don’t actually match to deployed artifacts. Without robust validation infrastructure, SBOMs create more noise than signal. Use cases like vulnerability correlation break down when the underlying data is untrustworthy.

Once you have reproducible builds and verifiable provenance pipelines, SBOMs become implicit in the process. The government was both premature and naive in requiring SBOMs before the ecosystem could reliably generate them and do something with them. More fundamentally, they hooed that mandating documentation would somehow solve the underlying supply chain visibility problem – unfortunately thats not the case.

But SBOMs are a symptom of deeper issues: unreproducible builds, opaque dependency management, and post-hoc artifact tracking. Simply requiring vendors to produce better paperwork was never going to address these foundational challenges. The mandate confused the deliverable with the capability.

What’s more concerning is what else disappeared. Provisions mandating phishing-resistant multi-factor authentication, real-time interagency threat sharing, and specific timelines for aligning federal IT procurement with Zero Trust requirements all vanished. The detailed Border Gateway Protocol security language was replaced with generic “agency coordination” directives. The EO stripped away near-term pressure on vendors and agencies alike.

Yet even as these enforcement mechanisms were being removed, the amendments introduced something potentially transformative.

Rules as Code: Promise, Paradox, and Perfect Timing

The most exciting addition is buried in bureaucratic language. A pilot program for “machine-readable versions of policy and guidance” in cybersecurity appears almost as an afterthought. While the EO doesn’t name OSCAL explicitly, this is almost certainly referring to expanding the Open Security Controls Assessment Language use beyond its current FedRAMP usage into broader policy areas.

This could be transformative. Imagine cybersecurity policies that are automatically testable, compliance that’s continuously verifiable, and security controls that integrate directly with infrastructure-as-code. OSCAL has already proven this works in FedRAMP: structured security plans, automated assessment results, and machine-readable control catalogs. Expanding this approach could revolutionize how government manages cybersecurity risk.

But there’s something deliciously ironic about the timing. We’re finally standardizing JSON schemas for control matrices and policy frameworks just as AI becomes sophisticated enough to parse and understand unstructured policy documents directly. It’s almost comical. Decades of manual compliance work have driven us to create machine-readable standards, and now we have “magical AI” that could theoretically read the original messy documents.

Yet the structured approach remains the right direction. While AI can parse natural language policies, it introduces interpretation variations. Different models might understand the same requirement slightly differently. OSCAL’s structured format eliminates ambiguity. When a control is defined in JSON, there’s no room for misinterpretation about implementation requirements.

More importantly, having machine-readable controls means compliance tools, security scanners, and infrastructure-as-code pipelines can directly consume and act on requirements without any parsing layer. The automation becomes more reliable and faster than AI interpretation. Real-time compliance monitoring really only works with structured data. AI might tell you what a policy says, but OSCAL helps you build systems that automatically check if you’re meeting it continuously.

This pattern of promising technical advancement while retreating from enforcement continues in the amendments’ approach to cryptographic modernization.

The Post-Quantum Reality Check

Then there’s the post-quantum cryptography provisions. The EO requires CISA and NSA to publish lists of PQC-supporting products by December 2025, and mandates TLS 1.3 by January 2030.

The TLS 1.3 requirement appears to be carried over from the previous executive order, suggesting this wasn’t a deliberate policy decision but administrative continuity. The amendment specifically states that agencies must “support, as soon as practicable, but not later than January 2, 2030, Transport Layer Security protocol version 1.3 or a successor version.” More tellingly, the 2030 timeline likely reflects a sobering recognition of enforcement reality: federal agencies and contractors are struggling with basic infrastructure modernization, making even a five-year runway for TLS 1.3 adoption potentially optimistic.

This reveals the central tension in federal cybersecurity policy. The infrastructure is calcified. Legacy systems, interception-dependent security architectures, and procurement cycles that move at geological speed all contribute to the problem. A 2030 TLS 1.3 mandate isn’t visionary; it’s an acknowledgment that the federal government can’t move faster than its most outdated components.

But this enforcement realism makes the broader PQC timeline even more concerning. If we need five years to achieve TLS 1.3 adoption across federal systems, how long will the actual post-quantum migration take? By 2030, the question won’t be whether agencies support TLS 1.3, but whether they’ve successfully migrated key exchange, digital signatures, and PKI infrastructure to post-quantum algorithms. That’s a far more complex undertaking.

In essence, the EO treats PQC like a checklist item when it’s actually a teardown and rebuild of our cryptographic foundation. Historically, the federal government has led cryptographic transitions by creating market demand and demonstrating feasibility, not by setting distant mandates. When the government moved to AES or adopted Suite B algorithms, it drove adoption through procurement pressure and early implementation.

Meanwhile, allies like the UK and Germany are taking this traditional approach with PQC. The UK’s National Cyber Security Centre has published detailed migration timelines and will launch a pilot program to certify consultancy firms that provide PQC migration support to organizations. Germany’s Federal Office for Information Security has been leading in co-developing standards and demonstrating early government adoption. They’re creating market pull through demonstrated feasibility, not regulatory deadlines that may prove unenforceable.

Beyond cryptography, the EO does introduce some concrete requirements, though these represent a mixed bag of genuine progress and missed opportunities.

The EO also tasks NIST with updating key frameworks and calls for AI-specific vulnerability coordination. All valuable work. But notably absent: any requirement for agencies to adopt, implement, or report on these updated frameworks.

One genuinely new addition is the IoT Cyber Trust Mark requirement: by January 2027, federal agencies must require vendors of consumer IoT products to carry the labeling. This represents concrete procurement leverage, though it’s limited to a narrow product category.

These mixed signals, technical infrastructure development alongside enforcement retreat, reflect a broader pattern that undermines the federal government’s cybersecurity leadership.

As we’ve explored in previous discussions of AI’s impact on compliance, this shift toward automated policy interpretation and enforcement represents a broader transformation in how expertise flows through complex systems, but only when the underlying mandates exist to make that automation meaningful.

We’re building this sophisticated machine-readable infrastructure just as the enforcement mechanisms that would make it meaningful are being stripped away. It’s like having a perfectly engineered sports car but removing the requirement to actually drive anywhere.

The Infrastructure Is Ready. The Mandate Isn’t.

Federal cybersecurity policy shapes vendor behavior, influences state and local government standards, and signals U.S. priorities to international partners. Without centralized mandates, vendors receive mixed signals. Agencies implement inconsistently. Meanwhile, international partners advance with clearer timelines and stronger enforcement. The U.S. risks ceding leadership in areas where it built the foundational standards, just as adversaries accelerate their own capabilities.

The United States has built remarkable cybersecurity infrastructure. OSCAL for automated compliance, frameworks for secure software development, and draft PQC standards for cryptographic transition all represent genuine achievements. But the June 2025 amendments represent a retreat from the leadership needed to activate this infrastructure.

We have the tooling, standards, and momentum, but we’ve paused at the moment we needed to press forward. In the face of growing threats and global urgency, discretion is not resilience.

We’ve codified trust, but stopped requiring it, leaving security to agency discretion instead of institutional design. That’s not a strategy. It’s a hope. And hope is not a security control.

Rethinking Compliance: AI, Skill Liquidity, and the Quest for Verifiable Truth

In an earlier piece, ‘The Limitations of Audits,’ we explored how traditional compliance frameworks often fall short, functioning as point-in-time assessments rather than drivers of continuous security practices. Building on that foundation, and expanding on our exploration in ‘When AI Injects Liquidity Into Skills: What Happens to the Middle Tier?’, let’s examine how AI is poised to transform this landscape by introducing “skill liquidity” to compliance and auditing.

The High Price of Illiquid Expertise: Manual Bottlenecks in Compliance Today

As I’ve lamented before, the real cost of traditional, “illiquid” approaches to compliance expertise is staggering. In WebTrust audits, for instance, audit teams frequently report not having “enough time to look at the big picture” because their efforts are consumed by manual, repetitive tasks. Approximately 5-10% of an entire audit engagement – which can range from 350 to well over 1,500 hours for the audit firm alone – is often dedicated just to mapping organizational policy documents against standard templates. Another 15-20% of those hours are spent scrutinizing core operational processes mandated by frameworks, such as user access lifecycles or system change logs.

These percentages represent an enormous drain of highly skilled human capital on work that is largely automatable. And these figures only account for the auditors’ direct engagement. The true cost multiplies when you factor in the mountain of preparation by the entity being audited and subsequent review by third parties. The fully loaded headcount costs across this ecosystem for a single audit cycle represent a heavy tax on expertise that remains stubbornly “frozen” in manual processes.

First-Wave Automation: A Trickle of Skill Liquidity, or a New Kind of Friction?

The first wave of automation has arrived, with tools like Vanta and Secureframe offering streamlined pathways to certifications like SOC 2 by generating policy templates and automating some evidence collection. For many organizations, especially those with simpler, cloud-native environments, this has made basic compliance more accessible, a welcome “trickle of skill liquidity” that helps get a generic certification done in record time.

However, this initial wave has inadvertently created what we might call “automation asymmetry.” These tools predominantly empower the audited entity. When a company uses sophisticated automation to produce voluminous, perfectly formatted artifacts, while auditors still rely on largely manual review, a dangerous gap emerges. The truth risks getting lost in these “polished milquetoast” audits. The sheer volume and veneer of perfection can overwhelm human scrutiny, potentially masking underlying issues or a compliance posture that’s merely superficial. The audit can devolve into a review of well-presented fiction rather than an unearthing of operational fact.

Unlocking True Skill Liquidity: Intelligent Systems That Make Deep Compliance Knowledge Flow

To move beyond surface-level automation or basic Large Language Models (LLMs), we need intelligent compliance systems – sophisticated platforms designed to embed and scale deep domain knowledge. This isn’t just about processing text; it’s about an AI that understands context, relationships, history, and the intricate rules of specific compliance frameworks from the perspective of all stakeholders. Indeed, this drive to embed and scale specialized knowledge through AI is a significant trend across industries. For instance, leading professional services firms have been developing proprietary generative AI platforms, like McKinsey’s Lilli (announced in 2023), to provide their consultants with rapid access to synthesized insights drawn from vast internal knowledge bases, effectively enhancing their own ‘skill liquidity’ and analytical capabilities. Such systems, whether for broad consulting or specialized compliance, require:

  • An ontology of expertise: Encoding the structured knowledge of seasoned auditors—controls, their intent, interdependencies, and valid evidence criteria.
  • An ontology of documents: Understanding the purpose and interplay of diverse artifacts like System Security Plans, policies, vulnerability scans, and their connection to the compliance narrative.
  • Temporal logic and change tracking: Recognizing that compliance is dynamic, and analyzing how policies, controls, and evidence evolve over time, identifying drift from baselines.
  • Systemic integration: A cohesive architecture of LLMs, knowledge graphs, rule engines, and data connectors that can ingest, analyze, and provide auditable insights.

This approach transforms an AI from one that simply helps prepare artifacts to one that can critically assess them with genuine understanding – a crucial shift towards making knowledge truly usable (a concept we delve into in ‘From Plato to AI: Why Understanding Matters More Than Information’ ) – making that deep compliance knowledge flow across the ecosystem.

Liquidating Rote Work, Elevating Human Expertise: AI’s Impact on Audit Value and Integrity

When auditors and program administrators leverage intelligent systems, the nature of their work fundamentally changes—a direct consequence of “skill liquidity.” The AI can ingest and critically analyze the (potentially voluminous and auditee-generated) artifacts, performing the initial, labor-intensive review that consumes so many hours. This liquidates the rote work, significantly impacting even the global delivery models of audit services, as routine document review tasks are often offshored for cost savings, can now be performed with greater consistency, speed, and contextual insight by these intelligent systems.

This frees up high-value human experts to:

  • Focus on what truly matters: Shift from the minutiae of “collection, ticketing, whether there was testing involved, whether there was sign-off” to the crucial judgment calls: “Is this a finding or a recommendation?”
  • Investigate with depth: Dive into complex system interactions, probe anomalies flagged by the AI, and assess the effectiveness of controls, not just their documented existence.
  • Enhance audit integrity: By piercing the veneer of “polished” evidence, these AI-augmented auditors can ensure a more thorough and truthful assessment, upholding the value of the audit itself.

The New Compliance Economy: How Liquid Skills Reshape Teams, Tools, and Trust

This widespread skill liquidity will inevitably reshape the “compliance economy.” We’ll see:

  • Transformed Team Structures: Fewer people will be needed for the easily automated, “liquid” tasks of data collection and basic checking. The demand will surge for deep subject matter experts who can design, oversee, and interpret the findings of these intelligent systems, and who can tackle the complex strategic issues that AI surfaces.
  • Empowered Audited Organizations: Companies won’t just be scrambling for periodic audits. They’ll leverage their own intelligent systems for continuous self-assurance, drastically reducing acute audit preparation pain and eliminating those “last-minute surprises.” Furthermore, the common issue of “accepted risks” or Plans of Action & Milestones (POA&Ms) languishing indefinitely is addressed when intelligent systems continuously track their status, aging, and evidence of progress, bringing persistent, transparent visibility to unresolved issues.
  • New Proactive Capabilities: With compliance intelligence more readily available, organizations can embed it directly into their operations. Imagine Infrastructure as Code (IaC) being automatically validated against security policies before deployment, or proposed system changes being instantly assessed for policy impact. This is proactive compliance, fueled by accessible expertise.

Trust is enhanced because the processes become more transparent, continuous, and validated with a depth previously unachievable at scale.

The Liquid Future: Verifiable, Continuous Assurance Built on Accessible Expertise

The ultimate promise of AI-driven skill liquidity in compliance is a future where assurance is more efficient, far more effective, and fundamentally more trustworthy. When critical compliance knowledge and sophisticated analytical capabilities are “liquefied” by AI and made continuously available to all parties—auditees, auditors, and oversight bodies—the benefits are profound:

  • Audited entities move from reactive fire drills to proactive, embedded compliance.
  • Auditors become true strategic advisors, their expertise amplified by AI, focusing on systemic integrity.
  • Compliance Program Administrators gain powerful tools for consistent, real-time, and data-driven oversight.

The journey requires a shift in perspective. Leaders across this ecosystem must recognize the risks of automation asymmetry and the limitations of surface-level tools. The call, therefore, is for them to become true orchestrators of this new compliance liquidity, investing not just in AI tools, but in the expertise, updated frameworks, and cultural shifts that turn AI’s potential into verifiable, continuous assurance. This is how we move beyond the “polished milquetoast” and forge a future where compliance is less about the performance of an audit and more about the verifiable, continuous truth of operational integrity, built on a bedrock of truly accessible expertise.