The Real Reason Your Cybersecurity is Broken
Most cybersecurity failures aren't technology failures. They're leadership failures. Nobody handed your executive team a job description for cyber, and that gap is exactly where incidents happen.
In this episode I break down what every C-suite role actually owns when it comes to cybersecurity: the CEO's personal SEC liability, the COO's workflow problem, the CFO who has to translate cyber risk into dollars, the CMO and CRO arguing over who owns customer data, the difference between a CIO, CTO, and CISO, the CHRO's role in making security a professional standard, and the coordination gap that quietly produces the illusion of a security program instead of the real thing.
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Watch the video version: https://youtu.be/2m5Pis8amp0
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Independent fractional CIO for owners of $5M to $50M businesses. Technology and cybersecurity strategy, with no tools to sell, no commissions, and no conflict.
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Transcript
John Barker (2025): That's why most executive teams fail at cybersecurity.
Speaker:It's not because they don't care.
Speaker:It's not because they're not smart.
Speaker:It's because nobody ever handed them a job description for it.
Speaker:So what happens, they hand it off to IT or their technical department.
Speaker:CEO goes back to running the business feeling like the problem is being handled.
Speaker:Problem is, it's not being handled.
Speaker:Cybersecurity is not an IT problem, or not an IT problem exclusively.
Speaker:It is a business problem that requires a technical solution.
Speaker:And until every executive in your organization understands their
Speaker:specific role, not IT's role, but their own role, you have a gap.
Speaker:And that gap is exactly where incidents happen.
Speaker:Today, I'm gonna give each member of your leadership team their lane, the
Speaker:CEO, the COO, the CFO, the CMO, the HR executive, and the technical leaders,
Speaker:the CIO, the CTO, the CISO, because those three titles are not the same thing,
Speaker:so let's go.
Speaker:The CEO.
Speaker:We start at the top because everything downstream reflects this.
Speaker:The CEO's job in cybersecurity is not to understand every technical control.
Speaker:It is not to read every policy document.
Speaker:It is one thing, visibly champion the culture.
Speaker:That's it.
Speaker:That is the non-negotiable because here's what I've watched happen in
Speaker:organization after organization.
Speaker:The CEO skips the annual security training.
Speaker:Maybe they're busy, maybe they get an exemption, maybe nobody has
Speaker:the nerve to tell them that they couldn't skip it, and every single
Speaker:employee in that company noticed.
Speaker:Culture does not flow up.
Speaker:It flows down.
Speaker:I've seen negative impacts of people feeding off negative emotional
Speaker:state of senior leadership.
Speaker:So if the person at the top treats security policy as optional, it becomes
Speaker:optional at every level below them.
Speaker:The CEO who clicks a phishing link because they never completed
Speaker:training is not an IT failure.
Speaker:That's a leadership failure.
Speaker:The CEO also owns the risk appetite of the organization.
Speaker:How much risk is this organization willing to accept?
Speaker:That's a business decision, not a technical one.
Speaker:It cannot be delegated to a tactician who does not understand the financial and
Speaker:reputational stakes of getting it wrong.
Speaker:The CEO signs off on the risk profile or the risk profile
Speaker:is a work of pure fiction.
Speaker:And one more thing, and I want you to hear this clearly if you have
Speaker:investors, government contracts, or any public-facing obligations.
Speaker:The SEC now requires public companies to disclose material
Speaker:cybersecurity incidents and their cybersecurity governance practices.
Speaker:Executives can face personal liability for misrepresenting their
Speaker:organization's security posture.
Speaker:This is not hypothetical.
Speaker:This is a regulatory reality that changed the stakes of CEO abdication permanently.
Speaker:Ignorance is no longer a defense, it is a liability.
Speaker:The COO, chief operations officer, owns obviously operations, and
Speaker:here's what most COOs don't realize.
Speaker:The way your business operates is your threat landscape.
Speaker:Every workflow that involves data, who touches it, how it moves, where
Speaker:it's stored, which system it passes through, that workflow is either
Speaker:reducing your exposure or expanding it, and a change in workflow can sometimes
Speaker:eliminate a risk entirely without spending a single dollar on a new tool.
Speaker:Here's a concrete example of what I mean.
Speaker:I work with a group of employees who are generating significant email, so
Speaker:they were exposed to a lot of phishing.
Speaker:There was accidental data sharing, a lot of the usual stuff.
Speaker:The instinct was to train them and add a filter, maybe even buy another platform.
Speaker:That's what the IT team recommended.
Speaker:But when we looked at the actual workflow, we realized those
Speaker:employees had no legitimate business reason to send or receive external
Speaker:emails from the company at all.
Speaker:So we turned it off.
Speaker:We whitelisted the only addresses that were operationally necessary.
Speaker:The risk wasn't managed, it was eliminated.
Speaker:No ongoing costs, no ongoing exposure.
Speaker:That was not an IT decision.
Speaker:That is a business decision and required someone who understood the operation well
Speaker:enough to redesign it and approve it.
Speaker:I'll take credit for redesigning.
Speaker:The COO's job is to ask that question first before the
Speaker:purchase order goes through.
Speaker:Does this workflow need to exist the way it currently exists?
Speaker:If the COO isn't in that conversation alongside the security team, you're
Speaker:patching holes in a boat instead of just redesigning the boat.
Speaker:CFO, the chief financial officer Most small and midsize organizations
Speaker:don't have a senior technical leader.
Speaker:They have tacticians, someone excellent at executing, keeping the lights on, managing
Speaker:infrastructure, maintaining the systems.
Speaker:What they often can't do is translate technical risk into financial impact.
Speaker:This is where the CFO has to show up.
Speaker:The CFO's role is to understand, at a business level, what a cyber
Speaker:incident actually costs, not the ransom number, but the real cost.
Speaker:Downtime multiplied by daily revenue, lost contracts, legal liability,
Speaker:regulatory fines, reputational damage that doesn't appear on a balance sheet
Speaker:but absolutely shows up in the pipeline.
Speaker:When the CFO owns those numbers, they can have a real conversation
Speaker:with the technical team about appropriate investment levels.
Speaker:They can help a tactician who doesn't know how to make the business case
Speaker:actually make a business case.
Speaker:They can evaluate a proposed security budget against real
Speaker:risk the way they would evaluate any other business investment.
Speaker:Without that, what you get is a CFO treating cybersecurity as strictly
Speaker:a cost center that needs to be minimized as much as possible.
Speaker:And I can't tell you how many times I've watched that become the most
Speaker:expensive decision a company ever made.
Speaker:So let me tell you a story involving a CFO.
Speaker:I was advising an organization that had hundreds of millions of dollars in assets.
Speaker:They were a small company, but the value of what they were sitting
Speaker:on was incredibly significant.
Speaker:The data storage was completely decentralized, when I first got involved.
Speaker:There was no centralized access control, and technically,
Speaker:the fix wasn't complicated.
Speaker:The harder part, which is usually always the harder part, was changing
Speaker:that behavior of staff who had built their entire workflow around
Speaker:the old way of doing things.
Speaker:Probably heard the saying, "We've always done it that way."
Speaker:Hate that.
Speaker:So we got there.
Speaker:One person at a time, we moved the organization to a centralized,
Speaker:protected structure, except for the CFO.
Speaker:We had discovered the CFO had been using his personal email for the
Speaker:bulk of his business communications, not occasionally, routinely.
Speaker:Financial documents, vendor contracts, strategy, all of it throwing, flowing
Speaker:through his own personal account.
Speaker:And because of that, his adult children, who helped him with his computer at
Speaker:home, had access to anything that had ever passed through that account.
Speaker:I want to be precise about what that means.
Speaker:This wasn't a hypothetical risk This was an active, uncontrolled access
Speaker:point to very sensitive business assets.
Speaker:People outside the organization with no vetting, no accountability, and no
Speaker:awareness of what they were touching.
Speaker:This wasn't malicious.
Speaker:This is somebody who had worked at the same organization for forty years.
Speaker:His workflow was his workflow.
Speaker:Change at that point felt…
Speaker:It didn't feel like we were upgrading anything.
Speaker:It felt more like we were accusing him of doing something wrong, even though
Speaker:he helped with the approval process.
Speaker:So but we made significant progress.
Speaker:I believe we improved the situation dramatically, but I'm gonna
Speaker:be honest, I don't know that we ever fully closed that gap.
Speaker:And that story is not a technology story, it's a leadership story.
Speaker:Because if the CFO's role had been clearly defined from the start, there
Speaker:had been standards in place that they were measured against, there was no
Speaker:policy sitting in a handbook, but let's just say that conversations happened
Speaker:differently, the, that accountability would occur before certain behaviors
Speaker:become a habit and certain behaviors that would become a bad habit.
Speaker:CMO or the CRO, so you got your chief marketing officer and your chief revenue
Speaker:officer, and they sit on something most of them don't even think of as a security
Speaker:problem, most likely, customer data.
Speaker:Every lead, every client profile, every purchase history, every
Speaker:behavioral data point that your marketing team collects, this is a
Speaker:data asset and someone has to own it.
Speaker:And let me give you a distinction real quick on, on data.
Speaker:The CMO and the CRO, your chief marketing officer and chief revenue
Speaker:officer, are the data owners.
Speaker:The IT team, or whoever is protecting it, the data, is just the custodian.
Speaker:Ownership means accountability.
Speaker:The CMO decides what data is collected, why, how long it's
Speaker:retained, and who has access to it.
Speaker:The technical team implements the controls, but they can't define what the
Speaker:data means to the business or what the exposure looks like if it's compromised.
Speaker:When a breach involves customer records, it's not IT that faces that client.
Speaker:It is the relationship owners, your sales team, your marketing
Speaker:team, your account management team.
Speaker:Those leaders need to understand what they're holding, why they're
Speaker:held accountable for it, because when something goes wrong, the customer
Speaker:is calling them, not your internal help desk or your MSP provider
Speaker:CIO, the CTO, and the CISO.
Speaker:these three titles get used interchangeably in smaller organizations
Speaker:or even rolled up into a singular position, but as you grow, you'll
Speaker:find out that they are not the same.
Speaker:The CIO, or the chief information officer, is usually focused on information
Speaker:systems that support business operations.
Speaker:How does the data flow?
Speaker:How systems align with the business goals.
Speaker:Lot more operationally oriented.
Speaker:The CTO, your chief technology officer, is a lot more focused on technology
Speaker:as a product or a competitive capability, how technology can
Speaker:drive growth and market positioning, and they can be more externally
Speaker:focused or also be very involved with developing, you know, systems
Speaker:with inside your business to handle those from a technology perspective.
Speaker:And then your CISO, your chief information security officer, is
Speaker:specifically responsible for protecting the organization's information assets.
Speaker:You've got your risk management, your incident response, security strategy.
Speaker:The entire job is telling you the truth about your exposure.
Speaker:Now, for most small and mid-sized businesses, a
Speaker:full-time CISO is not the answer.
Speaker:The title isn't the point.
Speaker:The function is the point.
Speaker:You need a voice in the room whose only job is to represent risk honestly without
Speaker:being structurally conflicted with peoples responsible for keeping operations
Speaker:moving or hitting revenue targets.
Speaker:What that looks like in practice depends on the size and complexity of your
Speaker:organization, but the question to ask is simple: Who in your organization
Speaker:can tell the CEO something is a serious risk without it threatening their
Speaker:own operational priorities or budget?
Speaker:If you can't answer that, the function doesn't exist.
Speaker:chief human resources officer.
Speaker:the last role most organizations will put on this list is the senior HR executive.
Speaker:Honestly, it may also be overlooked here's the current reality in most companies.
Speaker:Your IT department writes an acceptable use policy for technology
Speaker:equipment in the business.
Speaker:Legal reviews it, HR puts it in the employee handbook.
Speaker:Employees sign the employee handbook during the onboarding process,
Speaker:and then it just disappears.
Speaker:Honestly, honestly ask yourself, how often has an employee revisited the
Speaker:company handbook after starting the job?
Speaker:Hmm, anybody?
Speaker:Nobody is measuring employees against cybersecurity standards
Speaker:the way they are measured against sales targets or performance goals.
Speaker:Training completion rates exist, but completion of training is not
Speaker:necessarily competency, particularly if you're only doing it once a year.
Speaker:So clicking through a thirty-minute module once a year is not the same
Speaker:as demonstrating those behaviors that prevent incidents year-round.
Speaker:Accidental breaches will happen.
Speaker:Careless breaches will happen, not because employees are bad people, but
Speaker:because nobody tied the behavior to accountability in a way that employees
Speaker:actually felt it in their working lives.
Speaker:The HR executive owns performance frameworks.
Speaker:They are the person who can make security behaviors a professional standard,
Speaker:not a punishment, just an expectation, the same way you measure accuracy,
Speaker:the same way you measure attendance.
Speaker:That is an HR design problem as much as it is a security problem.
Speaker:missing piece, the quarterback.
Speaker:All right, I've given you six lanes, and I can already hear the
Speaker:questions forming in your head.
Speaker:Who makes sure all these people are actually talking to each other?
Speaker:Because right now in most organizations, nobody does.
Speaker:The CEO thinks the COO has it covered.
Speaker:The COO assumes IT is handling it.
Speaker:IT is waiting on a budget approval from the CFO.
Speaker:The CFO doesn't know what number to approve because nobody translated
Speaker:the risk into financial terms, and the CMO has never been in that
Speaker:conversation once in their life.
Speaker:Everyone assumes someone else is holding the thread, and in that assumption,
Speaker:the thread disappears entirely.
Speaker:This is not a technology problem.
Speaker:This is a coordination problem, and it is the reason that organizations
Speaker:with decent tools, reasonable budgets, and well-intentioned people still
Speaker:get hit with a cyber incident because the lanes I just described exist on
Speaker:paper, but nobody is functioning as the quarterback across all of them In large
Speaker:organizations, that role is the CISO.
Speaker:In smaller organizations, that function needs to exist in some form,
Speaker:whether it's internal or external, full-time or fractional part-time,
Speaker:because without it, every one of those lanes operates in isolation.
Speaker:a security posture.
Speaker:They produce the illusion of one.
Speaker:So here's the truth.
Speaker:Every executive in your organization is already accountable for cybersecurity.
Speaker:The incident doesn't ask who was responsible before it
Speaker:decides who gets blamed after.
Speaker:What I've given you today is not a new burden.
Speaker:It's just clarity.
Speaker:And clarity is the thing that turns a vague organizational anxiety
Speaker:into a set of specific actions owned by specific people or roles.
Speaker:CEO owns the culture.
Speaker:Sign the risk appetite.
Speaker:Understand that your personal behavior sets the standard
Speaker:for every person below you.
Speaker:COO, your workflows are your threat landscape.
Speaker:Redesign before you spend.
Speaker:CFO, learn what incident actually costs.
Speaker:Then help your technical team make the case and language
Speaker:the business understands.
Speaker:CMO and CRO, you own the customer data, not IT.
Speaker:Act like it.
Speaker:CIO, CTO, CISO, know the difference and make sure whoever owns security
Speaker:in your organization isn't conflicted with potentially other priorities.
Speaker:Chief Human Resource Officer, CHRO, the handbook is not accountability.
Speaker:Build security in how people are actually measured.
Speaker:then find your quarterback.
Speaker:Because six well-defined lanes with no one coordinating across them is still a gap.
Speaker:The organizations that get this right are not the ones with the biggest
Speaker:budgets or the most sophisticated tools.
Speaker:They're the ones where every executive knows their role and someone is making
Speaker:sure those roles actually connect.
Speaker:I sat across from executives in every one of these roles.
Speaker:The ones who get breached are rarely the ones who didn't care.
Speaker:They're almost always the ones who assumed someone else had it.
Speaker:Don't be that organization.
Speaker:If this raised questions about which of these lanes is currently empty in your
Speaker:company, that's the right reaction.
Speaker:Sit with it, and if you want to go deeper on any one of these
Speaker:roles, let me know in the comments
