Executive red teaming in high-stakes environments: Strategic leadership considerations for CISOs

Welcome reader to a 🔒 pro subscriber-only deep dive 🔒.

Brought to you by:

👉 Cypago - Cyber governance, risk management, and continuous control monitoring in a single platform

Forwarded this email? Join 70,000 weekly readers by signing up now.

#OpenToWork? Try our AI Resume Builder to boost your chances of getting hired!

—

Get lifetime access to our deep dives, weekly cyber intel podcast report, premium content, AI Resume Builder, and more — all for just $799. Corporate plans are now available too.

Executive Summary

In response to the surge of sophisticated cyberattacks targeting major organizations, executive teams are increasingly turning to "red teaming" — comprehensive adversarial simulations that stress-test security defenses. This report offers practical guidance for CISOs in high-risk sectors like finance, healthcare, critical infrastructure, and technology who need to establish executive-level red teaming programs that demonstrably strengthen their organization's security posture and operational resilience.

Our analysis reveals that executive-driven red teaming yields significant quantifiable outcomes:

• 25% fewer security incidents and 35% lower costs per security incident at organizations conducting regular red team exercises

• Measurable improvement in Mean Time to Detect (MTTD) and Mean Time to Respond (MTTR) metrics

• Organizations with well-tested incident response capabilities save over $2 million per breach compared to those without

Beyond technical metrics, executive-level red teaming produces critical qualitative benefits:

• Sharpened decision-making under pressure at the C-suite level

• Improved cyber literacy and situational awareness among board members

• Strengthened cross-functional coordination during crisis response

• Enhanced security culture from top-down engagement

This report integrates both recent data and expert CISO perspectives to provide a comprehensive framework for implementing successful executive red teaming programs, addressing governance structures, best practices, and practical implementation guidance.

Introduction: The Strategic Imperative for Executive Red Teaming

High-profile cyberattacks in recent years have prompted executive leadership teams to adopt red teaming – full-scope adversarial simulations – as a core component of organizational resilience. In high-stakes corporate environments (finance, healthcare, critical infrastructure, tech, etc.), boards and C-suites are no longer passive observers of cybersecurity drills but active participants in red team exercises that stress-test their companies' defenses and their own crisis response capabilities.

For CISOs operating in these high-risk environments, executive-level red teaming has emerged as a powerful tool to drive more effective security postures across three critical dimensions:

1. Technical resilience – identifying and remediating security gaps before real adversaries can exploit them

2. Organizational preparedness – testing crisis management, communications and recovery capabilities

3. Leadership effectiveness – building executive decision-making skills under pressure

Our analysis draws on the latest (2024–2025) data, case studies, and expert perspectives to provide CISOs with actionable insights for implementing effective executive red teaming programs. We examine both quantitative impacts (improved incident response times, reduced breach costs) and qualitative benefits (sharper decision-making, stronger interdepartmental coordination) across industries and regions.

As one CISO from a major financial institution noted: "Our technical red team operations were strong, but until we got the executive team in the room for immersive simulations, we never truly tested our organizational resilience. The gaps we found at the leadership level were eye-opening – and fixing them was more valuable than any technology investment we made that year."

Red Teaming in Context: Evolution and Current State

Red teaming is an adversarial exercise in which a group of ethical hackers (the "red team") simulates real-world attacks on an organization's technology, people, and facilities, while the defense (the "blue team") attempts to detect and respond. Unlike routine penetration tests, red team operations are goal-oriented, stealthy, and often unknown to most of the IT staff – only senior management typically knows a drill is underway.

What differentiates executive-focused red teaming is the extension beyond technical boundaries. These exercises typically include:

• Tabletop simulations in the boardroom to role-play incident scenarios

• Realistic "injects" – surprising plot twists that test decision-making under pressure

• Cross-functional participation engaging legal, communications, and business operations

• Stress-testing of crisis communication and business continuity plans

By 2024-2025, executive-level red teaming has gained broad traction across sectors. Many Fortune 500 firms and critical sector organizations now run comprehensive simulations at least annually, often with the help of third-party experts so that internal security leaders can participate fully.

Global regulators have also encouraged or mandated red team exercises for high-stakes industries. In financial services, the European Central Bank's TIBER-EU framework (Threat Intelligence-Based Ethical Red Teaming) has been adopted across 16+ countries. Similarly, the Monetary Authority of Singapore requires Adversarial Attack Simulation Exercises for banks. In North America, the U.S. Government's CISA leads programs like SilentShield that model nation-state level threats across critical sectors.

For the modern CISO, the question is no longer whether to implement executive red teaming, but how to structure programs that deliver measurable value to both security operations and leadership effectiveness.

Quantitative Impact: The Business Case for Executive Red Teaming

The business case for executive-level red teaming is compelling, with data showing clear improvements in security resilience metrics. By exposing security gaps and forcing organizations to fix them, red team programs help reduce both the frequency and severity of incidents over time.

Reduction in Security Incidents and Costs

According to research by Forrester, organizations that conduct regular red-team testing see 25% fewer security incidents on average and 35% lower costs per security incident. This translates to significant financial returns from red team investments.

Data from IBM/Ponemon reinforces this finding: companies with mature incident response plans and testing (including red/purple team exercises) save millions when breaches happen. By one estimate, firms with well-tested response capabilities saved over $2 million per breach compared to those without. For CISOs making the case for budget allocation, these hard metrics provide compelling justification.

Improved Detection and Response Capabilities

A key value metric is the improvement in Mean Time to Detect (MTTD) and Mean Time to Respond/Remediate (MTTR) to attacks. Executive red team exercises provide baseline data on detection rates for specific attack techniques, the number of alerts missed by the SOC, and how long it takes executives to mobilize a crisis team.

Over multiple test cycles, organizations typically see MTTD/MTTR numbers improve as they address gaps identified in previous exercises. One financial services firm documented a reduction in detection time from 24 hours to under 3 hours after implementing improvements identified in their executive red team program.

A comprehensive red team report should include:

• Heat maps of detection capability versus adversary TTPs

• Statistical tracking of MTTD, MTTR, and eradication success rate

• Gap analysis of security control effectiveness

These quantitative outputs guide informed leadership decisions on security investments, whether for new monitoring tools, additional SOC analysts, or enhanced training programs.

Business Continuity and Operational Resilience

Executive red team exercises frequently focus on worst-case scenarios (ransomware outbreaks, destructive attacks on critical systems) to test whether a company can maintain essential operations during attacks. These drills often uncover single points of failure or process breakdowns that would hinder continuity – allowing the company to fix them proactively.

In critical infrastructure sectors, metrics often focus on operational resilience:

• Percentage of critical processes maintained during simulated attacks

• Time to restore full operations after compromise

• Effectiveness of manual override procedures when systems are compromised

One major electric utility discovered through a red team exercise that their backup control capabilities weren't fully isolated from primary networks, creating a potential single point of failure. This finding led to architectural changes that significantly improved their recovery capabilities.

Compliance and Regulatory Benefits

Executive red teaming also delivers quantifiable benefits in regulatory compliance. A case study from Kroll illustrates this: an international trading firm conducted a 3-month executive red team engagement after its CEO and board became concerned about unseen vulnerabilities. The exercise revealed significant security gaps and enabled the firm to demonstrate to regulators that they had implemented a robust testing program.

By proactively addressing critical vulnerabilities, the firm became "less likely to face the potentially huge cost of a major security breach" and could also avoid regulatory fines under strict financial mandates. This preventative approach yields measurable ROI in avoided penalties and compliance costs.

Many organizations now track "risk retirement" metrics from red team exercises, measuring:

• Number of critical findings addressed within 30/60/90 days

• Reduction in the organization's cyber risk score after remediation

• Improved ratings in regulatory examinations

A striking example comes from the financial sector, where TIBER-EU framework testing has been conducted on over 100 financial entities, delivering "concrete results that have helped improve cyber resilience" of critical financial services. For CISOs, these programs provide a structure to demonstrate measurable security improvements to regulators.

Qualitative Benefits: Leadership and Organizational Transformation

Beyond hard metrics, executive red teaming yields rich qualitative benefits that improve an organization's security posture, crisis management capabilities, and leadership effectiveness.

C-Suite Decision-Making Under Pressure

Red team scenarios force executives to confront fast-moving, ambiguous situations – such as a coordinated ransomware attack unfolding across global operations with limited information. By experiencing these high-pressure drills, leadership teams develop what security professionals call "muscle memory" for cyber crisis response.

CISOs report that after executive red teaming, their leadership teams show measurable improvements in:

• Speed and quality of decision-making during real incidents

• Confidence in implementing the incident response plan

• Understanding of when to invoke key decisions (system shutdown, external notification)

• Ability to manage competing priorities during crisis

As one expert observed, "an ill-thought-out response can wreak more havoc than the attack itself" – red teaming helps prevent this by conditioning leaders to make better decisions under extreme pressure. High-quality simulations typically include realistic elements like panicked customer communications, media inquiries, or regulator questions, training executives to manage multiple stakeholders while containing technical threats.

This leadership preparation is especially critical given the fast-evolving nature of threats. In one financial services organization, the CEO credited their quarterly tabletop exercises with giving him the confidence to make a rapid decision to isolate regional networks during a suspected attack – a choice he admitted he would have hesitated on without the practice sessions.

Board-Level Cyber Literacy and Engagement

A frequent challenge for CISOs has been translating technical security concepts for board understanding. Red teaming serves as a powerful educational tool that bridges this gap. Instead of abstract discussions about risk, boards witness concrete demonstrations of potential attack paths and business impacts.

After participating in red team exercises, boards typically show:

• Improved ability to ask relevant questions about security posture

• Greater understanding of the organization's true security maturity

• More informed oversight of security investments

• Stronger support for remediation of identified gaps

One CISO reported that after a board-witnessed red team demonstration showing how attackers could move from a compromised vendor portal to core financial systems, directors immediately approved funding for a network segmentation project that had been previously deferred. The exercise changed the conversation from theoretical risks to demonstrated vulnerabilities with clear business implications.

This phenomenon is consistent with research findings that boards more readily fund security initiatives after participating in simulations that make abstract threats tangible. For the strategic CISO, this represents a powerful alignment tool that transforms security from a cost center to a business enabler.

Cross-Functional Coordination and Communication

Real cyber incidents demand seamless collaboration between technical teams (IT, security) and business units (legal, PR, operations). Executive red teaming rigorously tests these communication pathways across organizational silos.

Exercises typically involve representatives from across the enterprise:

• CISO and technical security team

• CIO/CTO and IT operations

• Legal and compliance

• Corporate communications

• Human resources

• Business unit leaders

• Customer-facing operations

These simulations quickly illuminate coordination breakdowns that could prove disastrous in real incidents. Organizations often discover critical gaps – such as Operations not being looped in early about a production outage, or Legal having insufficient preparation for multi-jurisdiction breach notification requirements.

One healthcare CISO discovered through a tabletop exercise that their biomedical engineering team, which managed connected medical devices, had never been included in cyber incident response planning. This insight led to the creation of formal coordination protocols between IT security and biomedical engineering, significantly improving their ability to respond to potential attacks on clinical systems.

The value of identifying these gaps during simulations rather than real attacks is immeasurable. By testing and strengthening cross-functional coordination in advance, organizations can ensure they respond as a unified team rather than competing silos during actual incidents.

Security Culture Transformation

When executive leadership actively engages in red teaming, it sends a powerful message throughout the organization that security is a top priority. This tone-from-the-top approach has cascading effects on overall security culture.

CISOs report that organizations with strong executive red team programs typically experience:

• Increased employee reporting of suspicious activity

• Higher completion rates for security awareness training

• Greater compliance with security policies

• More proactive engagement from business units on security matters

One technology firm institutionalized a quarterly "Chaos Day" program where executives rotated through the role of "incident commander" during simulated attacks. The program normalized breach response practice across the organization and created a blameless culture of fast reporting. Over time, they tracked a significant reduction in "dwell time" for simulated insider threats – from weeks down to days – as employees became more comfortable identifying and escalating suspicious activities.

This cultural transformation extends to third parties as well. Organizations with mature red team programs often include key vendors in exercises, strengthening the security posture of their entire supply chain ecosystem.

Subscribe to CybersecurityHQ Newsletter to unlock the rest.