Rethinking Risk Assessment in Cybersecurity

Cybersecurity risks have become more complex and unpredictable than ever, yet many companies struggle to quantify these threats in terms that truly matter. How can CFOs and CISOs effectively communicate about risk, make smart security investments, and navigate the emerging challenges posed by AI? In this episode, CJ interviews Andy Ellis, a renowned cybersecurity leader, former CISO of Akamai, investor, director, advisor, leadership coach, and author of the book 1% Leadership. Andy unpacks why most companies measure risk the wrong way and breaks down his "Pyramid of Pain” framework for categorizing it. He discusses the dynamics between CFOs and CISOs in purchasing security tools, demystifies security budgeting and vendor negotiations, dives into the evolving role of AI in security operations, and explains why the CISO and CIO roles are on a collision course. Andy also reveals insider stories from the frontlines of major breaches, shares a compelling risk analogy inspired by vampires and zombies, and clears up once and for all why the demise of the Death Star was not a failure of risk management.

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LINKS:

Andy Ellis on LinkedIn: https://www.linkedin.com/in/csoandy

Andy Ellis on X: (@CSOAndy) https://x.com/csoandy

Website:

https://www.csoandy.com

1% Leadership: https://www.amazon.com/1-Leadership-Master-Improvements-Leaders/dp/0306830817

How to CISO:

https://www.howtociso.com

Duha One:

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

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TIMESTAMPS:

(00:00) Preview and Intro

(02:49) Sponsor – Rillet | Pulley | Brex

(07:23) Defining Risk: Technical & Human-Friendly Perspectives

(09:20) Actuarial Risk Versus Human-Driven Risk

(15:33) Why the Demise of the Death Star Wasn’t a Failure of Risk Management

(16:58) Sponsor – Aleph | RightRev | Navan

(21:22) How the Death Star Metaphor Relates to Real-World Security Breaches

(23:20) Why Risk Should Not Be Quantified in Dollar Terms

(25:15) The Pyramid of Pain: Risk Severity and Surprise Levels

(30:21) How CFOs and CISOs Should Partner on Security Purchases

(34:03) Are Security Budgets Over or Under-Spent?

(36:22) Balancing Budget for Security Tools and People

(39:48) Tips for FP&As on Brokering the Security Budget With Your CISO

(44:10) Factoring AI Uncertainty in a Three-Year Security Roadmap

(46:38) AI Washing in Security Products and Realistic Impact

(48:55) The Limitations of Security Operations

(50:53) The Future of CIO and CISO Roles and Organizational Reporting

(54:55) Why IT Shouldn’t Report to the CFO

(57:18) Israeli Unit 8200 and Cybersecurity Innovation

(59:50) Startups Versus Public Companies: Differing Risk Models

(1:02:52) Wrap

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#Cybersecurity #RiskManagement #CISO #SecurityOperations #SecurityFinance

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