The Security Strategist 7 August 2026 27 MIN

Why CISOs Struggle to Explain Cyber Risk to the Board

“If you can demonstrate that the likelihood of experiencing a disruption because of AI is higher in numbers, that will change the minds of any boardroom. This applies to any industry, from public sector and banking, financial, manufacturing, defence, energy."

Every CISO out there faces one key challenge: the challenge of getting the board to acknowledge cybersecurity as a top enterprise risk management priority. 

According to the ClearPoint Strategy Strategic Planning Report, only 51 per cent of active strategic and corporate projects maintain a steady Green status. The remaining 49 per cent fluctuate between Amber and Red, requiring varying levels of intervention.

This goes to show that many investment decisions are reliant on red, amber and green dashboards and not on financial exposure. According to Mike Saxton, CRO at MyCiso, the issue relates to cyber reporting often lacking portability. “A director may be highly experienced and commercially sophisticated, but still struggle to compare risk posture between organisations because the underlying reporting models are inconsistent.”

With AI also in the picture now, the speed and scale of attacks is rapidly rising; that gap is becoming harder to defend. 

This is why in the recent episode of The Security Strategist podcast, E360Tech’s host Shubhangi Dua, Tech Journalist and Podcast Producer, was joined by Asdrúbal Pichardo, CEO at Squalify, 3x SaaS CEO, Board Advisor, Start-Up Mentor, Non-Executive Director. 

This podcast breaks down how to actually turn technical risk into something the rest of the business can realistically manage, measure, and report on.

Translating Cyber Risk for the Boardroom: A CISO’s Guide to Financial Quantification

Pichardo says when it comes to cyber risk, it's time to avoid reporting based on qualitative metrics; instead, portray more quantitative metrics. This means really talking to the executives and the boards in the language of business “which is money.”

"CISOs need to rely less on qualitative assessments. They need to translate the cyber risk into financial figures so the board will understand the implications of cyber."

CISOs typically present cyber risk through technical metrics, maturity scores and vulnerability reports, but boardrooms tend to avoid making decisions based on technical language. This is why translating that cybersecurity technical jargon into metrics is essential for boardrooms. They think in terms of financial exposure, business resilience and return on investment (ROI).

The  CEO of Squalify explains why the future of cybersecurity leadership depends less on explaining threats and more on quantifying business impact. He puts up a case for enterprises requiring a common language that is comprehensible by both security teams and executives instead of relying on technical dashboard data.

Leveraging AI Vulnerability Detection: The Strategic Advantage of Mythos

Artificial intelligence (AI) has made it more complex from every corner. AI-driven cyber attacks are on the rise. On the other side, AI is being deployed by defenders to protect their platforms as well as to optimise the speed and effectiveness of AI tools and integrate it into their workflows. Ultimately, AI has, for better or worse, blurred the line between cybersecurity, governance and business continuity. 

To put into perspective, Dua asked Pichardo about Anthropic's Mythos model’s incredible vulnerabilities-spotting capabilities. He said that Mythos is causing a lot of dialogue in the industry right now, but the vulnerability-discovering capabilities had existed for years, and those tools went unnoticed. 

While industry individuals may be concerned about attackers taking advantage of AI tools like Mythos, enterprises should be able to access the same technology to identify and fix those weaknesses before attackers exploit them. However, geopolitical tensions and other economic disparities have made it hard for enterprises to access.

The key idea is that defenders have an advantage because they know their own systems. He says, “The hacker doesn't have the knowledge, or the source code from your enterprise. You already have it, so enterprises need to get there with Mythos before the hacker comes to you with Mythos.”

The issue he spotlights is that American companies have been given access to Mythos, but the US government has restricted access outside of the nation. 

“At the end it should it should it should get into the right hands because it's probably already in the wrong hands,” the CEO states.

The conversation around Anthropic’s Mythos model depicts a shift in the enterprise tech and cybersecurity industry. While much of the discussion has focused on how attackers might exploit increasingly capable AI, Pichardo sees the greater opportunity for defenders.

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For boardrooms, the new question they must pose is whether enterprises are optimising AI quickly, efficiently, and, most of all, safely to minimise risks before adversaries get to it. The recent cyberattack by a rogue OpenAI AI model on Hugging Face was an eye-opener for all. In a worst-case scenario, imagine if the hackers’ AI agents began penetrating secure enterprise tech platforms at a rate that’s hard to fend off their strikes.

AI has moved from being a technical capability to a strategic investment decision one that should be measured in business impact rather than technology adoption.

“If you can demonstrate that the likelihood of experiencing a disruption because of AI is higher in numbers, that will change the minds of any boardroom. This applies to any industry, from public sector and banking, financial, manufacturing, defence, energy,” notes Pichardo. 

He added that at Squalify’s mother company, Munich Re, the world's largest cyber reinsurer ensures that AI’s impact on cyber risk is visible not only from a technical perspective but a business perspective as well. 

"It goes beyond tech or IT; it's processes, governance, business operations.”

Ultimately, enterprises need to quantify cyber risk so they are better able to defend against the AI-driven threat landscape at any given time. 

Takeaways

  • Cyber risk quantification is becoming a boardroom necessity
  • AI is increasing attack velocity, not just sophistication
  • Defensive AI can create a competitive advantage
  • Cyber and AI risk are converging into enterprise risk
  • Board AI literacy is becoming a strategic capability

Chapters

00:00 Understanding Cyber Risk in Business

02:42 The Differences in Cyber Risk Management: US vs Europe

05:42 The Evolution of Risk Management with AI

08:46 Quantifying Cyber Risk: The Role of Squalify

11:34 Real-World Applications: Onboarding Clients at Squalify

14:53 The Importance of Financial Metrics in Cybersecurity

17:38 AI's Impact on Cybersecurity and Business Operations

20:20 The Future of AI in Cyber Risk Management

23:32 Key Takeaways for CISOs and Board Members

Watch the full episode of The Security Strategist Podcast to hear Asdrúbal Pichardo discuss cyber risk quantification, AI governance, boardroom communication and what enterprise leaders should prioritise next.

Shubhangi Dua
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Podcast Host, Producer & B2B Tech Journalist, EM360Tech