Phishing experts are upping their game to hunt for C-suite whales

Phishing attacks are nothing new. However, over the past few years, there’s been a sharp rise in one particular type: whaling phishing. While phishing traditionally casts a wide net, targeting any unsuspecting individual, whaling goes after the big fish: C-suite executives and senior leaders within an organization. These attacks take more time, effort, and technical expertise from the attackers, but the rewards are far greater.

Whaling attacks are typically more sophisticated, using methods such as CEO impersonations, deepfake technology, and targeted spear-phishing. Recent figures indicate that 89% of phishing emails now involve impersonation of someone familiar to the recipient. Some 16% percent of those emails involve the attacker posing as a colleague. In the case of whaling, this means targeting an executive, or someone with access to critical resources like bank accounts.

The cost of falling victim to a phishing attack can be significant. The FBI reported $52 million in losses from phishing scams in 2022 alone. Such costs are borne not only by businesses but their customers as well, not to mention the resources that need to be spent on prevention.

These types of attacks are hard to ignore, given the potential scale of the financial and reputational stakes involved. For businesses, however, they offer an opportunity to refocus efforts on protecting the most valuable targets in their organizations. In this article, we’ll explore this growing trend and offer practical advice for how organizations can bolster their defenses.

Why is whaling trending?

Phishing generally casts a wide net, with attackers relying on the sheer size of their mailing list for an unsuspecting victim to click a link. In contrast, whaling phishing is highly targeted and customized. Attackers take the time to research their victims.

This includes gathering personal details, understanding their business responsibilities, analyzing email habits, and creating highly personalized content to dupe recipients. This level of effort may seem labor-intensive, but it pays off significantly when it succeeds.

After all, whaling targets individuals with the power to approve financial transfers or access sensitive corporate data, making them prime candidates for malicious actors seeking large payoffs. Likewise, executives are potentially less likely to have undergone thorough threat detection training, and, because they’re so busy, are more likely to overlook telltale signs of a scam.

One case that highlights the growing sophistication of whaling attacks occurred in 2023 when a multinational firm in Hong Kong was defrauded for $25 million through deepfake video calls impersonating the CFO and other key corporate executives. A finance manager with access to the funds was misled to transferring this big amount of money seemingly at the behest of the bosses.

Such attacks often rely on emotional manipulation, creating urgency or exploiting business relationships to trick victims into making impulsive decisions, like authorizing wire transfers or providing confidential login details. In an enterprise setting, where not every business leader knows every executive, the dangers are all the more potent.

For attackers, the appeal of these high-value targets is clear. The more effort spent personalizing the attack, the greater the potential financial return. In many cases, the sheer scale of the damage, both financial and reputational, can have long-term consequences for the victim company.

An evolving playbook

Phishing tactics have become far more sophisticated in recent years. This is driven by the increased use of artificial intelligence (AI) and machine learning technologies. One notable evolution is the use of deepfakes, in which attackers use AI-driven filters to impersonate executives or other trusted figures in video calls.

The technology for live deepfake calls is now widely available and is often so convincing that the victim would often find no reason to question their authenticity, especially when the request appears legitimate. This technique was a key factor in the 2023 Hong Kong case, where attackers pretended to be the CFO in a deepfake video call to authorize the wire transfer.

Deepfakes are only one part of the equation, though. Whaling attackers also use spoofed email addresses, social media profiles, and even phone numbers to further mask their identities. The goal is to make the attack as convincing as possible, relying on the victim’s trust in their communications to bypass security protocols.

Attackers are also getting better at creating a sense of urgency. By crafting messages that appear to come directly from the CEO or another senior executive, they push other executives to act quickly, without second-guessing their actions. This technique is often referred to as “CEO fraud” and remains one of the most common strategies employed in whaling attacks.

This fraud exploits the hierarchical structure of businesses, whereby people are more likely to comply with an urgent request from a superior.

Protecting your organization

As the sophistication of high-level phishing increases, so too must the defenses designed to protect against it. Business leaders and security professionals should implement a multi-layered approach to safeguard sensitive data and prevent executive-targeted scams. Here are some critical steps.

Employee Training and Awareness. One of the most effective ways to defend against whaling attacks is to educate employees, especially those in finance and leadership positions, on how to spot suspicious activity. Training should cover identifying red flags, such as unfamiliar sender addresses, unexpected requests, or high-pressure tactics. Regular phishing simulation exercises can help reinforce this knowledge and keep awareness high.

Multi-Factor Authentication. Multi-factor authentication (MFA) is one of the simplest yet most effective tools to thwart attackers, especially when it comes to protecting high-value accounts. Requiring multiple forms of verification (e.g., password plus biometric or token-based authentication) adds an additional layer of protection that can make it more challenging for attackers to bypass.

Email Filtering and Anti-Phishing Software. Implementing advanced email filtering systems can help detect suspicious messages before they reach an employee’s inbox. Anti-phishing software can flag email addresses that are inconsistent with the company’s domain, alerting employees to potential impersonation attempts. These systems should be fine-tuned to detect subtle signs of phishing, such as slightly misspelled domain names or unusual attachments.

Incident Response and Reporting Protocols. Having a clear protocol for reporting suspicious communications and responding to potential security breaches is crucial. This includes establishing a chain of command for verifying unexpected requests and ensuring that all employees know the steps to take if they receive a suspicious email, text or call.

Third-Party Risk Management. Attackers don’t only target an organization specifically but can also target third-party vendors who have access to company networks, so it’s essential to manage these relationships carefully. Regular security audits, strong contractual obligations, and clear data-sharing policies can help mitigate the risk posed by external parties.

Staying ahead of the curve

As whaling phishing attacks continue to rise, organizations must be proactive in strengthening their defenses. The evolving tactics used by cybercriminals demand a multi-layered, comprehensive approach that goes beyond traditional security measures. Protecting C-suite executives and other high-value targets is no longer optional, but rather a critical part of safeguarding an organization’s financial stability, data, and reputation.

By focusing on continuous training, implementing advanced technological solutions, and developing robust incident response plans, businesses can minimize the risk of falling victim to these highly sophisticated attacks. Preparation is key, and staying ahead of emerging trends will give your organization a fighting chance.

Featured image credit: Kasia Derenda/Unsplash