At a Glance
Kayne McGladrey, Founder & Principal Cybersecurity and AI Governance AdvisorFocus Areas: AI Governance, Cybersecurity, Risk Management, Security Thinkers360 In-Depth Profile & Portfolio: Kayne McGladrey Social Media: LinkedIn Books: Cyber Risk is a Myth: A Business Approach to Integrated Risk Management Framework: GRC Maturity Model Highlighted Content: Enterprises Slowed Down and Nobody Told the Employees, When Governance Theory Meets Legal Reality. Thinkers360 Awards & Recognition: Top 50 Global Thought Leaders and Influencers on Cybersecurity 2026, Top 50 Global Thought Leaders and Influencers on Security 2026, Top 50 Global Thought Leaders and Influencers on AI Governance 2025. |
Thought Leader and Influencer Interview
Thinkers360 thought leader interviews profile prominent members of the Thinkers360 community who embody the power of ideas in their work. In this edition, we speak with Kayne McGladrey, cybersecurity leader, advisor, author, and AI governance expert.
With more than twenty years of experience in cybersecurity leadership, including two tours as a CISO in highly regulated environments, Kayne brings a business-focused perspective to cybersecurity, risk management, and AI governance. In this conversation, he shares insights on bridging the gap between security teams and business leaders, integrating cybersecurity into enterprise risk management, his new book Cyber Risk is a Myth, thought leadership, and the importance of evidence-based communication in cybersecurity.
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Thinkers360: Tell us a bit about your background and areas of expertise
KM: I’ve spent over twenty years in cybersecurity leadership, including two tours as a CISO in highly regulated environments, and I’ve advised organizations across three continents. Somewhere along the way I noticed that security teams and executives kept having the same conversation in two different languages, and everyone acted like that was normal. It’s not. It’s expensive.
I help take cybersecurity out of its technical silo and treat it like every other business risk. I’m a CISSP, a senior IEEE member, and the author of Cyber Risk is a Myth: A Business Approach to Integrated Risk Management, published by CRC Press. I also developed the GRC Maturity Model because I got tired of watching organizations grade themselves on compliance checklists and call it risk management.
Thinkers360: What are your current responsibilities and what does a typical day look like?
KM: I run an independent advisory practice serving SMBs and mid-market firms – companies with enterprise-level risk but no enterprise-level budget for a full-time CISO. A lot of my job involves translation, like turning technical risk into board-ready decisions, and occasionally turning board fantasies about security back into technical reality.
Mornings belong to client work. Afternoons drift toward writing: newsletter issues, articles, and interviews. Since 2017, I’ve spoken to the press over 300 times and counting, and people ask how I find the time. Explaining security clearly to a reporter and explaining it to a board are the same skill, so the time isn’t wasted, and I have a professional responsibility to help make cybersecurity accessible.
Thinkers360: The title of your new book, Cyber Risk is a Myth, is quite provocative. Can you tell us about the book and why you wrote it?
KM: The title is a provocation with a point. The cybersecurity industry has created an artificial distinction between “cybersecurity risk” and “business risk,” and that distinction causes bad decisions. If your manufacturing plant goes offline, it matters remarkably little to your income statement whether the cause was ransomware or a hurricane; the lost production and missed deliveries land the same way either way. The root cause matters far less than the business outcome.
I wrote the book because I kept watching brilliant people talk past each other. Often, this is where security teams speak in vulnerabilities and patches, but executives think in revenue and operational continuity. That communication gap costs real money; I’ve watched it derail budgets and delay decisions that couldn’t afford to wait.
The book draws on court cases, stock market data, and hard evidence to make a simple case: when properly understood and communicated, security risks are business risks, and they deserve the same financial framing, language, and decision processes as any other business risk. CRC Press published it, and the downloadable resources are free at kaynemcgladrey.com/myth, because security leaders shouldn’t have to re-create existing tools or figure out how to run a business integration workshop.
Thinkers360: What’s your favorite part of your current role?
KM: The moment a client’s leadership team stops nodding politely at security updates and starts arguing with each other about priorities. Risk has stopped being a compliance ritual and become a business conversation with stakes and trade-offs, which is the whole reason I do this work.
A close second is hearing from readers who took an idea from the newsletter or the book and used it to win an argument they’d been losing for years, usually with someone who outranks them. Cybersecurity as a profession spends a lot of time complaining it isn’t invited to the grown-ups’ table. My favorite part of my job is pulling up chairs.
Editor’s Note: See Kayne McGladrey’s profile to work with him directly.
KM: LinkedIn is an echo chamber dressed as a megaphone. Thinkers360 is how I get ideas in front of people who don’t already agree with me, which is valuable feedback and engagement. I contribute articles, participate in interviews like this one, and use the platform’s community of enterprise buyers and fellow analysts to see which framings travel beyond my own feeds. If an idea survives contact with people who evaluate thought leadership for a living, it’s probably sturdy.
Thinkers360: How do you like to work with brands who wish to engage you as a thought leader?
KM: Directly, and early. The worst engagements are ones where a brand arrives with the conclusion already written and asks me to fill in some blanks. I’m an advisor, not a ventriloquist’s dummy, and honestly, the dummy market is crowded anyway.
The best engagements start with a real question, like a strategy that needs stress-testing, a message that needs translating for an executive audience, a position on AI regulation or risk management that needs grounding in evidence rather than assertion. And they’re not a one-off, but rather part of a longer multi-channel campaign, because a single written piece of content isn’t going to change most buyers’ minds.
Finally, I only say things in public I can defend in front of a room full of people who might disagree with me. That last filter saves everyone a lot of trouble.
Thinkers360: What’s your main advice for upcoming thought leaders?
KM: Have a defensible position, not a content calendar. The internet does not need another LLM burping up content weekly about cybersecurity. It needs people willing to say something that could be wrong, show the evidence, and survive the disagreement.
Three practical additions. First, write like you talk, because if your thought leadership sounds like it was assembled by committee, readers can tell. Second, put your ideas somewhere durable; a book or a model with your name on it compounds, while a hot take evaporates by Thursday. Third, show your receipts. Nothing bothers me more when content doesn’t have links to sources, because it forces readers to either decide that they trust you implicitly or go validate your claims or assertions.
The last thing is patience. The book I just published grew out of positions I staked out years ago. Thought leadership is a long position. Most people day-trade it, which is why most of it is forgettable.
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