Red Teaming in the AI Era: Why Your Strongest Defense Is the Offense

Severin Sorensen
8 hours ago
7 min read

Two forces above all are rewriting the rules of risk and opportunity: the explosive proliferation of Artificial Intelligence and the pervasive, systemic nature of cybersecurity risk.

We invest millions in "Blue Teams"—our dedicated defenders—and in next-generation AI platforms, believing these digital moats will protect our castles. We run compliance audits, pass penetration tests, and present reassuring dashboards to the board. This creates a dangerous, often fatal, illusion of security. The modern adversary does not follow our compliance checklist. They don't care about our audit reports. They seek the one, unanticipated seam in our socio-technical system.

This is why the most resilient organizations are embracing a counter-intuitive strategy: they are paying a dedicated, expert group to think, act, and attack like the enemy.

This is the modern Red Team.

The 21st-century Red Team is a multi-disciplinary capability designed to pressure-test the entire organization—its technology, its processes, and, most importantly, its people—against the full spectrum of real-world threats. Understanding and championing this function is quickly becoming a core component of effective stewardship.

The New Threat Landscape

The urgency for strategic Red Teaming is driven by a fundamental shift in the nature of our vulnerabilities. The "attack surface" is no longer just our network. It is our data models, our executive decision-making, our brand reputation, and the cognitive biases of our employees.

The AI Accelerator

AI is a dual-use technology of staggering power. While we rightly focus on its potential to drive productivity and create new value, our adversaries are focused on its potential to break systems. For example:

Attack Tool: Adversaries are now using AI to craft hyper-realistic, individualized spear-phishing emails at scale. They are creating "deepfake" audio and video of executives to authorize fraudulent wire transfers or manipulate stock prices. They are using AI to discover novel software vulnerabilities far faster than human defenders can patch them.
Attack Target: The AI models we deploy are themselves targets. Adversaries are no longer just trying to steal data; they are trying to corrupt it. They can "poison" the data our machine learning models train on, subtly skewing their outputs to cause financial miscalculations, flawed strategic forecasts, or operational chaos. They can launch "evasion attacks" that trick our AI-powered security tools into ignoring a real threat.

A traditional security audit cannot find these vulnerabilities. Only an adversarial mindset—one that actively seeks to manipulate the logic of your AI—can reveal these new, systemic risks.

The Cybersecurity Reality

Simultaneously, our digital estates have become impossibly complex. The move to a hybrid-cloud, remote-work, and IoT-enabled world means the "perimeter" is gone. Risk is distributed everywhere: in a partner's insecure API, an employee's home network, or a misconfigured cloud server.

Cybersecurity is a business-wide operational risk. For example, a ransomware attack doesn't have the ability to just lock data; it could halt production lines, collapse supply chains, and trigger regulatory fines that erase a year's profit. The "Blue Team" is tasked with defending this borderless territory 24/7. It is an impossible task to do perfectly because they are, by definition, reactive. The Red Team provides the crucial, proactive counterbalance.

Beyond "Finding Holes"

A Red Team's objective is not to find a flaw, it is to achieve a mission. This is the critical distinction. A penetration test asks, "Can a hacker get in?" A Red Team engagement asks, "Can an adversary with a specific, strategic goal achieve that goal, and would we even know it was happening?"

This goal could be:

"Exfiltrate the unannounced M&A target list from the CEO's executive assistant."
"Subtly alter the financial data in the ERP system to be 2% off for the quarterly report."
"Trigger a physical shutdown of the manufacturing plant via the operations network."
"Use a deepfake of the COO to convince the PR team to release a false, damaging statement."

When executed correctly, the Red Team delivers strategic value that reverberates far beyond the CISO's (Chief Information Security Officer) office.

Forging True Operational Resilience

Resilience is the ability to function through a failure. A Red Team exercise is the only practical way to simulate a full-scale crisis, as it tests your entire response playbook.

When the Red Team "breaches" the network at 2 a.m., what happens? Is the Security Operations Center (SOC) alerted? Does the incident response plan activate? Do Legal, Communications, and the executive leadership team convene? Does the C-suite know what decisions to make, or is there confusion and panic? The Red Team exposes the friction, gaps, and flawed assumptions in your human response system, arguably the part that matters most in a real crisis.

De-Risking Innovation and AI Deployment

We are pushing our teams to deploy AI faster to gain a competitive edge. This creates immense pressure to cut corners. The Red Team acts as the essential "quality control" for strategic risk.

Before you launch that new AI-driven pricing engine, the Red Team should be tasked with trying to fool it. Before you integrate an AI-powered chatbot for customer service, the Red Team should test whether it can be tricked into revealing private customer data or manipulated into giving harmful advice that creates legal liability. This "Adversarial Validation" turns the Red Team from a security function into a critical partner for the Chief Innovation or Chief Data Officer.

Optimizing Security ROI

The global cybersecurity market is worth hundreds of billions of dollars. Your organization is likely spending a fortune on sophisticated tools. But are they working? Are they configured correctly?

A Red Team provides the hard data. If your team can bypass a $10 million "Next-Generation" security platform using a simple, known technique, you have an integration problem, not a technology problem. This allows leaders to stop wasting money on "shelfware" and invest in the people, processes, and tools that demonstrably stop real-world attacks.

Calibrating the Human Firewall

Technology is only half the picture. Time and again, the initial entry point for a major breach is a human. The Red Team's "social engineering" campaigns are powerful diagnostic tools for assessing organizational culture and awareness.

When the Red Team sends a (safe) simulated phishing email crafted with AI, who clicks? More importantly, who reports it? Do employees leave sensitive documents on their desks? Do they plug in USB sticks found in the parking lot? These tests provide a "ground truth" metric for the efficacy of your security training programs, allowing you to target your efforts where they are truly needed.

Assembling and Integrating the Modern Red Team

How a Red Team is structured and where it reports is central to its success. Putting it in the wrong place guarantees its failure.

Models of Operation

There are three primary models, each with trade-offs:

Internal Team: A permanent, in-house group.
- Pros: Deep understanding of the business context, culture, and "crown jewels." Can operate continuously and build long-term relationships.
- Cons: Expensive. Can "go native" and become insular, losing its adversarial edge. May fear political blowback for finding flaws in a powerful executive's division.
External (Third-Party): Hiring a specialized firm for time-boxed engagements.
- Pros: Brings a "fresh eyes" perspective and cutting-edge techniques learned from attacking other organizations. No political allegiances.
- Cons: Lacks internal context. Can be very expensive per engagement. Focus is often more tactical than strategic.
Hybrid Model (The Gold Standard): A small, internal Red Team "cell" that manages the program, partners with business units, and contracts external specialists for major, "no-holds-barred" operations. This model provides the best of both worlds: internal context and external, unbiased expertise.

Composition: The "A-Team"

A modern Red Team is a multi-disciplinary unit that mirrors a real adversary's capabilities:

The Operator/Hacker: The technical expert who can find and exploit vulnerabilities in code, networks, and cloud infrastructure.
The Social Engineer: A specialist in psychology and influence, adept at bypassing human defenses through phishing, vishing (voice), and physical infiltration.
The Intelligence Analyst: The strategist who researches the organization from the outside, identifies high-value targets, and designs the overall campaign (mimicking the Tactics, Techniques, and Procedures of a real group).
The AI Specialist: The new, essential member who understands how to attack and manipulate machine learning models.
The "Insider" (Rotational): A rotating member from Legal, Finance, or Operations who can provide "ground truth" on what really matters to the business and help design plausible, high-impact scenarios.

Where Does a “Red Team” Report?

A Red Team must have organizational independence.

Bad: Reporting to the CISO (Chief Information Security Officer). This is a direct conflict of interest. The CISO's job is defense (the Blue Team). You cannot have the "attacker" reporting to the "defender" they are meant to be testing. Findings will inevitably be softened, filtered, or buried to protect the CISO's reputation.
Better: Reporting to a "peer" of the CISO, such as the Chief Risk Officer (CRO), the Chief Operating Officer (COO), or the head of Internal Audit. This ensures independence and that the findings are treated as an organizational risk, not just an "IT problem."
Best: Direct, "dotted-line" access to the Board's Audit or Risk Committee. This provides the ultimate top-cover, ensuring the Red Team is protected from internal politics and that its most critical findings are seen unfiltered by the one body that can mandate enterprise-wide change.

When to Engage

The Red Team is a continuous capability. While a full-scale, "gloves-off" exercise might be conducted annually, the Red Team should be engaged at specific, high-risk moments:

Pre-Launch: Before any major new product, especially an AI-driven one, goes to market.
Post-M&A: Immediately after an acquisition, to test the newly integrated (and often highly vulnerable) network and systems.
New Infrastructure: Before "go-live" on a new cloud environment or ERP system.

The Main Takeaway

The Red Team serves one ultimate purpose: it replaces assumptions with data. It is the ultimate tool for challenging groupthink and fostering a culture of "constructive paranoia.” Your role is the following:

To Champion Them: You must provide the executive sponsorship and political air cover they need to operate. You must make it clear to the organization that the Red Team's goal is to make everyone stronger, not to play "gotcha."
To Absorb the Findings: The Red Team's final report (known as the "out-brief") should be delivered to you. You must be willing to hear the unvarnished truth, even when it's painful.
To Act: The greatest failure is not learning from the simulated one. The Red Team's findings must be tracked, resourced, and fixed. The true value is realized in the follow-up. This "Purple Team" exercise—where the Red and Blue teams collaborate on lessons learned—is where real security maturity is built.

The Red Team is your strategic insurance policy. It is the independent, adversarial voice that tells you the truth, stress-tests your strategy, and forges the organizational resilience you need to not only survive the next crisis, but to thrive in spite of it.