Experience is the Multiplier: Why Cyber Leadership Still Matters in a Tool-Driven World

In today’s cybersecurity market, the rise of vCISO platforms and automation tools has made security leadership more accessible than ever. Dashboards, policy templates, and compliance frameworks promise faster implementation and broader reach, especially for startups, SMBs, and organizations with lean IT budgets.

However, a growing misconception is taking hold: that cybersecurity tools are a substitute for effective cybersecurity leadership.

They’re not.

You can’t automate judgment. And you can’t replace lived experience with scorecards.

The virtual CISO model is a smart evolution. It provides flexible, fractional leadership without requiring a full-time executive hire. And SaaS GRC platforms enable faster onboarding, structured delivery, and more transparent reporting.

But there's a hidden danger in treating these tools as the solution rather than as support.

As CSO Online bluntly puts it, “CISOs are not just technologists—they’re psychologists, educators, and diplomats.” https://www.csoonline.com/article/3846288/7-misconceptions-about-the-ciso-role.html        

Even a polished report means little without the strategic interpretation that prioritizes actions and communicates risk at the executive level.

Security leadership isn’t about checking a box. It’s about understanding when that box isn’t enough.

True CISO experience brings:

Risk Prioritization Under Pressure

• Tools may tell you what’s wrong. Only experience teaches you what actually matters.

Board-Level Communication

• Harvard Business Review notes, “The board should ensure that management aligns cyber risk management with business needs… and continuously monitors performance.” https://hbr.org/2023/06/4-areas-of-cyber-risk-that-boards-need-to-address

Contextual Policy Governance

• NIST’s SP 800-53 Rev. 5 emphasizes, “Controls are flexible and customizable… implemented as part of an organization-wide process to manage risk.” https://csrc.nist.gov/publications/detail/sp/800-53/rev-5/final

Operational Confidence During Crisis

• Real-world CISOs have guided breach response, managed multi-jurisdictional audits, and briefed boards in high-pressure situations. That wisdom can’t be downloaded.

As Robert Putrus, through ISACA, wrote, “Since the CISO position is being promoted to report higher in the organization chart, a greater emphasis is being placed on the CISO role and the expected skill level of those filling the role.” https://www.isaca.org/resources/news-and-trends/isaca-now-blog/2019/defining-the-role-of-the-ciso

None of this is a dismissal of tools. In fact, many leading vCISO programs, including my own, leverage platforms to enhance structure, visibility, and repeatability.

In my advisory roles with firms like Goliath Cyber Security Group and Rye Strategic Partners, I’ve seen firsthand how platforms like Maro (https://seekmaro.com), Cynet, and Cyrisma can be leveraged effectively when paired with strategic leadership and deep context. These partnerships succeed because experience guides the platform, not the other way around.

Tools help you move faster. Experience helps you move correctly.

The notion that CISOs are merely technical operators is outdated and detrimental. In reality, the modern CISO is a hybrid: part strategist, part translator, part crisis leader.

Sean Cleary says, “What Makes a Modern CISO? Today’s CISO needs to possess a wide array of skills—strategic vision, cross-functional leadership, and the ability to manage complexity—to successfully guide their organization through an increasingly uncertain landscape.” https://www.rivierapartners.com/decoding-the-modern-ciso-role-from-defender-to-strategic-partner        

vCISO programs are here to stay. That’s a good thing. But let’s be clear:

If your cybersecurity leadership can’t brief your board, prioritize risk under pressure, or influence the broader business, not just IT, then you don’t have a security strategy. You have a checklist.

In a 2024 follow-up, Forbes reinforced this point: “CISOs are evolving from tech experts to strategic leaders, central to corporate governance and risk management.” https://www.forbes.com/sites/rhettpower/2024/09/01/how-cisos-are-evolving-from-tech-experts-to-strategic-leaders/

The best tools in the world are only as effective as the judgment behind them. And in cybersecurity, judgment is earned, not automated.

Because when things go wrong, the dashboard won’t be in the room.

The leader will.