Phishing for CEOs: The Executive Email Trap That Keeps Catching You Out.

If you’re in the C-suite and think phishing is a “user problem,” we’ve got some unsettling news: you’re the user. And unfortunately, you’re the one wearing a high-vis vest and waving a giant flag that says, “Hit me here!” when it comes to cybercriminals.

According to the OAIC’s May 2025 Notifiable Data Breaches Report, phishing attacks were behind 84 reported breaches in just the second half of 2024. Each incident impacted an average of 1,220 people. These aren’t just minor inbox annoyances; they’re full-blown breaches with serious reputational, operational, and financial consequences. And when it comes to the mailboxes of senior leaders, attackers see them as the crown jewels.

Executive email accounts are a high-value target because they often contain sensitive strategy documents, privileged system access, and confidential financial communications. Once an attacker gets in, the damage doesn’t stop with a compromised inbox. It can include lateral movement, identity spoofing, and triggering fraudulent payments. In the age of AI, attackers have tools that make these scams even more believable: emails that match an executive’s tone, or deepfake voicemails authorising urgent fund transfers.

It’s worth reflecting on habits like forwarding documents to personal email, reusing passwords, or clicking dodgy links while multitasking. These are the cracks that become floodgates for compromise. No one’s immune, and phishing tactics are getting smarter and harder to spot.

Traditional email filters often fail to catch these threats. Legacy systems are built to detect spam and viruses based on known bad indicators. But modern phishing campaigns now use AI-generated messages, contextually appropriate requests, and time-delayed payloads to avoid detection. That’s why more organisations are turning to behavioural analytics that monitor patterns and flag anomalies—like a login attempt at 2am from an unexpected location.

To fight smarter phishing campaigns, you need smarter defences. AI-powered email security gateways use real-time analysis to understand sender behaviour, reputation scores, and linguistic markers. These tools detect impersonation and spoofing even when the email looks genuine.

Implementing Privileged Access Management (PAM) helps contain compromise by ensuring executive accounts don’t have always-on access. Just-in-time privileges are granted when needed and revoked afterwards, limiting lateral movement.

Phishing-resistant MFA is critical. It’s no longer enough to use SMS codes. Stronger methods like hardware tokens or certificate-based authentication offer a resilient second layer of protection.

Behaviour plays a big role too. That’s why security-conscious organisations are using microlearning and contextual nudges instead of traditional training marathons. Bite-sized, timely training builds good habits without creating fatigue.

So what can you do right now?
Review your current email security setup. Make sure you’ve deployed phishing-resistant MFA. Check that PAM limits lateral movement. And have a plan to respond quickly if a senior executive’s mailbox gets compromised. In a breach, time is everything.

Phishing is no longer a “click-here” problem; it’s a leadership issue. It affects how your organisation communicates, protects trust, and responds under pressure. If you’re still relying on outdated defences, your boardroom is at risk.

At Sustainabil.IT, we help Australian organisations build threat-informed defence strategies aligned to the real-world tactics targeting leadership teams. From AI-driven email security gateways to PAM solutions and phishing-resistant authentication, we help you protect what matters most: your people, your decisions, and your reputation.

Ready to shield your executive team from the next big phishing play? Get in touch.