Business risk, not just IT risk: Framing pen testing for the executive team

For business leaders, a penetration test (pen test) provides a window into how security gaps could impact core operations, customer trust, or compliance standing. For many organisations, it’s the logical first step in building a modern security program: it delivers a clear-eyed view of risk, helping prioritise what matters most. 

We often hear from IT leaders that a pen test is “the before photo” that gives them a tangible baseline of their organisation’s security posture. So, when they invest in uplift, they can come back later to do a new pen test and show how much they’ve reduced their risk exposure. 

At its core, the goal of pen testing is to identify vulnerabilities and connect them to consequences that business leaders care about.  When done well, it surfaces risks in a way that resonates beyond the IT department, highlighting the potential business-wide consequences of system vulnerabilities, from operational disruption to reputational damage. 

That’s why pen testing remains a powerful tool for CISOs and CIOs navigating a complex cybersecurity landscape. But its true value isn’t just in the technical results. Instead, it’s in how those results are translated into language the executive team understands: risk, impact, and return on investment (ROI).  

When positioned effectively, pen testing becomes a crucial source of truth for business leaders. Its findings are a catalyst for informed decisions, smarter investments, and a stronger, more resilient business. To unlock its full value, pen testing must be framed as a whole-of-business exercise that brings executives on the journey. 

A catalyst for meaningful change

A pen test goes beyond a ‘checkbox exercise.’ Unlike static risk registers or desktop audits, it stress-tests systems in real-world conditions.  

Unlike desktop audits, for example, which assess policies and processes on paper, a pen test directly probes the organisation’s live environment, highlighting real weaknesses based on observed evidence, not theoretical risk. 

Pen testing identifies misconfigurations, access loopholes, and high-risk entry points that might otherwise remain hidden threats. But more importantly, it helps tech leaders bring clarity, in the form of practical, actionable insights, to executive conversations. 

For every CIO that’s focused on managing risk and avoiding surprises, pen testing is an evidentiary tool. It helps connect technical weaknesses to business outcomes, whether it’s the cost of downtime, the reputational blow of a data breach, or the operational chaos of ransomware. For example, it’s not uncommon for a pen test to identify that anyone with access to an organisation’s corporate network could escalate privileges and take over the whole IT environment in under two hours, if they had the right skills. Findings like this are what moves the needle at an executive level, changing the cyber risk conversation from “what if?” to “how soon can we fix this?” 

Elevating the conversation

In many boardrooms, the security conversation is evolving. It’s no longer just about tools or controls; it’s about resilience and business continuity. Ask any systems leader looking for better outcomes, and they’ll tell you that pen testing helps drive that shift. 

That sentiment is echoed by other tech leaders, who see cybersecurity through a forward-looking, regulatory lens. With legal obligations mounting – including Australia’s Cyber Security Act 2024 and its mandatory ransomware reporting – the boardroom appetite for real-world risk assessment is growing. 

That’s why pen testing is increasingly part of the board’s oversight role: It’s protecting the enterprise, not just the network.

Making the case to the board

So how can tech leaders present penetration testing in ways that resonate with the c-suite? For starters, it’s all about storytelling.  

To get it across the line, you need more than a technical briefing; you need a compelling narrative. Framing the findings as a human-led story, with clear stakes and real-world consequences, is what makes board members sit up, care, and take action. 

First, ditch the jargon. Translate technical issues into impact statements: “This flaw could allow unauthorised access to customer data, which could trigger a notifiable breach under the Privacy Act.” Or: “An attacker could shut down our ERP system, halting orders for 36 hours.” 

Second, connect pen testing to strategy. Is your business expanding into new markets? Adopting SaaS tools? Embracing hybrid work? Or undergoing an IT integration because of a merger? Each of these increases attack surface, and pen testing is how you map and mitigate it. 

For many business leaders, the ‘aha’ moment comes when they see just how quickly a tester can escalate privileges or bypass safeguards that look good on paper but fail under real-world pressure. It is the moment cyber risk becomes real. 

Because the findings come from real-world testing, not theoretical scenarios, pen test reports offer the kind of concrete evidence boards increasingly expect. They’re a valuable asset when making the case for funding, addressing regulatory requirements, or guiding strategic decisions. 

Numbers that speak – Australian statistics

• ASD responded to over 1,100 cybersecurity incidents, with ransomware comprising over 10% of these incidents, indicating a persistent threat to Australian organisations. 
• ASD notified entities more than 930 times about potential malicious activity on their networks, reflecting the ongoing efforts to mitigate cyber threats. 
• Nearly 94,000 cybercrime reports were submitted to ReportCyber, averaging one report every 6 minutes, highlighting the frequency of cyber incidents in Australia. 
• Small businesses experienced an average financial loss of $46,000 per cybercrime report, emphasising the significant impact on the SME sector. 
• Critical infrastructure networks were regularly targeted, with incidents involving compromised accounts, networks, and denial-of-service attacks. 

It’s now a ‘business conversation’

These figures highlight why penetration testing can no longer be seen as optional. In fact, it’s a strategic asset, and one that helps organisations prove, improve, and prioritise their security investments. And with the right framing, it becomes a ‘business conversation,’ not just a technical one. 

To learn how Interactive can support your organisation’s cyber maturity journey with expert-led penetration testing and cyber advisory services, speak to a member of our team today.