VIP Impersonation: When Leadership Becomes the Target
(Part 3 of our Impersonation Playbook blog series)
If brand impersonation steals your company’s identity, VIP impersonation steals its leader’s voice.
Attackers know authority is persuasive. When the “CEO” sends an urgent request or “the CFO” asks for a wire transfer, employees respond fast, often faster than they verify. What looks like efficiency is actually vulnerability.
VIP impersonation turns trust inside out, using the people who define a company’s credibility as the bait.
From Con to Compromise
Impersonating authority isn’t a new trick, but AI has made it nearly foolproof. Before email, con artists would call pretending to be a manager or banker. Early phishing scams followed the same pattern: urgency, authority, and just enough detail to sound plausible.
By the 2000s, these scams evolved into what we call Business Email Compromise (BEC), or fake executive requests for funds, invoices, or sensitive data. Fast-forward to today, and attackers can mimic tone, grammar, and even voice using generative AI tools. The message doesn’t just look real, it feels real.
And the results speak for themselves: BEC remains one of the most financially damaging cybercrimes worldwide, costing billions annually.
How Attackers Target Leaders
Attackers study leadership patterns with the precision of marketers. They read press releases, earnings calls, and social posts to learn how executives communicate. From there, they build narratives that sound believable.
The most common tactics include:
- CEO or CFO fraud: Urgent payment or wire-transfer requests that exploit hierarchy and trust.
- HR or Legal pretexting: Fake requests for tax data, payroll information, or employee records.
- Supplier impersonation: Imitate trusted vendors asking for updated payment details.
- Deepfake communication: Synthetic voice calls or video messages that mimic executive tone and voice cadence.
Each of these bypasses technical defenses by relying on human trust, the hardest route to secure.
Investigating VIP Impersonation
When a message looks like it’s from the top, the response has to be fast and precise. The goal isn’t just to block the email. It’s to prove, with evidence, what actually happened.
Here’s how seasoned investigators approach it:
- Validate the communication chain: Compare sender domains, reply-to addresses, and message headers against known good patterns. Even minor anomalies, such as a missing character or a redirect, are signals.
- Correlate behavior, not just metadata: Does the message fit the sender’s usual tone, schedule, and workflow? Analyzing behavioral patterns helps distinguish a real executive from an imposter.
- Review financial and operational impact: Identify whether instructions were followed, funds moved, or data accessed. Even a single successful impersonation can ripple through multiple systems.
- Document the evidence trail: The strength of your investigation depends on transparency. Capture the decision path with how the message was verified, what data was referenced, and which controls stopped or missed it.
- Feed findings back into defenses: Every impersonation attempt offers intelligence. Use it to refine anomaly detection, authentication policies, and user awareness for next time.
This is where speed and structure matter most. An efficient investigation doesn’t just stop a loss, it preserves confidence across the organization.
Why Culture Is the Strongest Control
Technology helps, but culture decides outcomes. If employees feel pressured to act without questioning, impersonation tactics will keep working.
Leaders can change that dynamic by:
- Normalizing verification: Make it clear that confirming a request, even from the CEO, is expected, not insubordinate.
- Establishing clear channels: Define how high-risk instructions (like payment approvals) should be sent, verified, and logged.
- Supporting transparency: When incidents occur, share the learnings and how teams responded. This turns a mistake into a collective education opportunity.
- Reinforcing collaboration: Security, finance, and communications should operate as one unit in these cases. A single delay in escalation can cost millions, and teams that talk to each other close the window faster than those that don’t.
The Impersonation Series Comes Full Circle
Across this series, we’ve explored three sides of the same problem:
- Part 1: Why impersonation is resurging, fueled by AI.
- Part 2: How brands become the bait and what investigation looks like when your brand identity is hijacked externally.
- Part 3: How attackers use VIPs and leadership and why investigation speed and cultural readiness are your best defenses.
Across impersonation tactics, the pattern is clear: trust is the constant target.
Whether attackers imitate your logo or your voice, what they’re really trying to leverage is a recipient’s confidence in company communication, identity, and urgent decision-making.
Protecting that trust requires more than filters or takedowns. It requires systems that can investigate at machine speed and people empowered to question at human speed. That’s where the future of security lies.
