The Game Show: CISO Jeopardy! | How Many CISOs Does an Organization Really Need?

An artistic collaboration between Human Cognition and Artificial Intelligence | By Sean & TAPE3

Join us for an immersive fictional game show story that delves into the critical factors and decisions driving the number of CISOs an organization might need in today's complex cybersecurity landscape.

Let TAPE3 read this edition of the newsletter to you 🎧 🤖 ⇩


Setting the Stage: The CISO Conundrum

In an era marked by rapid technological advancements and evolving cybersecurity threats, one question frequently reverberates through the hallways of corporations, startups, and the minds of security professionals alike: How many Chief Information Security Officers (CISOs) does an organization need?

It's a question that doesn't have a one-size-fits-all answer. Factors like the size of the organization, the complexity of its business operations, the industry (or industries) it operates in, the types of data it handles, and its geographic footprint can all significantly influence this crucial decision. The question grows even more complex when you consider the changes in business development and service delivery models, accelerating pace of technological change, shifting regulatory landscapes, and emerging cybersecurity threats.

Understanding the right number and type of CISOs an organization needs is akin to solving a complex puzzle, one that can have dire consequences if not assembled correctly. Too few, and you risk leaving your organization vulnerable to a myriad of cybersecurity threats. Too many, and you might suffer from redundancy, inefficiency, and a drained budget.

To add a layer of complexity, the calculus isn't static. As organizations evolve, so too does the security landscape and the associated risks and regulations. In such a dynamic environment, how can decision-makers navigate this intricate web?

To explore this vital question, we've created a unique, entertaining, yet educational experience that pits industry experts against each other in a contest that simulates real-world scenarios.

Welcome to a special edition of Jeopardy! focused entirely on deciphering the CISO conundrum.

Whether you're a seasoned information security professional, an executive, or someone curious about the world of cybersecurity leadership, the following "CISO Jeopardy!" story aims to engage, educate, and prompt you to think deeply about how many CISOs your organization really needs—both today and in the future.

Now, let the games begin!


The Game Show: CISO Jeopardy!

[Opening theme music—the camera pans to the show's host, Alexa]

Alexa: "Welcome to a special edition of CISO Jeopardy! that tackles one of the most pressing issues in the world of business and technology today: How many Chief Information Security Officers does a company need? I'm your host, Alexa, and I’m delighted to introduce our contestants, all experts in the field of Information Security!"

[The camera pans to the contestants: Sarah, an experienced CISO; Chris, an IT consultant; and Jordan, a cybersecurity analyst]

Alexa: "Let's meet our contestants!"

[Sarah, Chris, and Jordan introduce themselves and share brief backgrounds]


Round 1: Small Business Woes

Alexa: "First Answer: This small business operates solely within the United States, has a lean IT team of five people, and manages a single e-commerce website. They handle moderate amounts of consumer data and, while experiencing target phishing campaigns on a regular basis, they have yet to experience a major cyber incident."

Sarah: "Why does this small business need only one CISO?"

Chris: "Why can this small business rely on their board for their CISO function?"

Jordan: "Why can this small business get away with zero CISOs and rely on external consultancy instead?"

Alexa: "Correct, Jordan! Given their small size, limited complexity, and moderate risk, this company could feasibly rely on external consultancy for now."


Round 2: The Power of Scale

Alexa: "Second Answer: This enterprise operates in 15 countries, manages a multitude of business units ranging from healthcare to finance, and handles sensitive data across all domains. They're currently dealing with new privacy regulations in multiple jurisdictions."

Sarah: "Why does this enterprise need multiple specialized CISOs?"

Jordan: "Why does this enterprise need to consider hiring temporary CISOs for each business unit?"

Chris: "Why does this enterprise need one CISO with a team of cybersecurity experts?"

Alexa: "Correct, Sarah! Given the international operations, diverse business units, and multi-jurisdictional regulations, having multiple specialized CISOs would be beneficial. Jordan's response is valid as well, but could leave cross-business-unit risk exposed."


Round 3: The Future is Now

Alexa: "Third Answer: This tech company operates mostly in the cloud and is heavily investing in IoT and AI technologies. They anticipate a significant growth spurt in the next five years."

Chris: "Why does this tech company need one CISO right now, but possibly more as they grow?"

Sarah: "Why does this tech company need to plan for multiple CISOs, specializing in AI, IoT, and Cloud Security?"

Jordan: "Why does this tech company need a single visionary CISO who can adapt and grow with them?"

Alexa: "Chris, you're correct! Given their current needs and future growth, having one CISO now, but being prepared to scale up by adding more specialized CISOs later, is likely the best approach."


Round 4: The Regulatory Maze

Alexa: "Fourth Answer: This financial institution is solely based in the U.S but has recently been hit with multiple cybersecurity incidents and faces strict compliance measures from federal agencies."

Jordan: "Why does this financial institution need a part-time CISO and supplement with external consultants?"

Sarah: "Why does this financial institution need one CISO to focus on federal compliance and another on incident response?"

Chris: "Why does this financial institution need one dedicated CISO for now, and reassess later?"

Alexa: "Sarah, you're correct again! Given the recent incidents and stringent compliance requirements, CISOs dedicated to the two core challenges they face would enhance their cybersecurity posture."


Final Round: A Balanced Approach

Alexa: "Fifth and Final Answer: This growing startup deals with consumer data but is extremely budget-conscious. They have an existing IT team but lack specialized security expertise."

Sarah: "Why does this startup need a Virtual CISO?"

Chris: "Why does this startup need to divide CISO responsibilities among the IT team?"

Jordan: "Why does this startup need a full-time CISO right away?"

Alexa: "Sarah, you're on fire! A Virtual CISO would offer them the expertise they need while fitting their budget constraints."


Think and Win

Alexa: "That wraps up our special edition of CISO Jeopardy! With 3 correct answers, Sarah takes the top spot today. We hope that this has not only been entertaining but has also given our audience, especially IT and information security professionals, much to ponder about the future needs of CISO roles in their organizations."

[Cameras pan out—Closing theme music]


While CISO Jeopardy! is fictional, the questions it raises are real and pressing for anyone in the field of Information Security. As the landscape evolves in terms of technological challenges and business complexity, so too will the requirements for effective cybersecurity leadership.

It’s not just about asking if you need a CISO, but how many and what kind you'll need to navigate the future securely. Keep in mind that sometimes the answer may very well be zero.


What's your perspective on this story? Want to share it with Sean on a podcast? Let him know!


This article represents the results of an interactive collaboration between Human Cognition and Artificial Intelligence.

Sincerely, Sean Martin and TAPE3

Enjoy, think, share with others, and subscribe to "The Future of Cybersecurity" Newsletter.

Want to comment on this topic, you can connect with Sean and the community in this LinkedIn post: https://www.linkedin.com/pulse/game-show-ciso-jeopardy-sean-martin


Sean Martin is the host of the Redefining CyberSecurity Podcast, part of the ITSPmagazine Podcast Network—which he co-founded with his good friend Marco Ciappelli—where you may just find some of these topics being discussed.

Or, visit Sean’s personal website.