The history of automation is the history of humans being freed up to do something more valuable.
Should you be scared of AI?
I am not going to tell you to be scared of AI because “it’s coming for your job”! No, I actually think AI is going to birth a hyper-productive economy where most people are going to be asked to do much more. (that’s a perspective of abundance) We’re living in a fear stage right now because the transition hasn’t happened and there are still many unknowns. But I’ll save those thoughts for another time…
Right now, what is striking to me is the level of sophistication coming from the AI powered social engineering camp. These are the bad guys across the globe that prey on people making mistakes in their every day job to hijack their technology. Ya, the old ransomware gangs.
Their playbook is the same, but it’s super powered using AI as a research and execution tool.
You have been taking the corporate sponsored Security Awareness Training, you’ve been passing the tests and you might be able to quickly spot a fraudulent email by now. (at least you’re suspicious)

Well, things are about to get a lot more difficult.
The new AI powered scams are fixing the grammar issue. They are analyzing the company and the employees, so they sound exactly like Steve from accounting. The AI can also allow scammers to build a huge database of personas and deploy sophisticated attacks that mimic each company’s style.
Here’s how they might deploy AI to phish large databases of companies.

If you dare to interact with an email, you might be chatting with an AI bot. Even more, that AI bot is going to know who works in your IT department and from social media scraping, they are also going to know more than enough to sound convincing.
This is a huge win for scammers, because they can now have quality and quantity. Prior to AI, scammers would need to target specific customers to sound convincing. It involved a lot of time and resources. Now they can still blast out campaigns but also raise the quality of those campaigns to a “targeted” level.
Real AI Scams
Deepfake Video Fraud Targeting Corporate Finance Teams (Global firm with U.S. ties, 2024)
A company employee joined a video call with what appeared to be real executives.
The entire meeting—including multiple participants—was AI-generated deepfake video.
The employee transferred $25 million based on instructions from the fake leadership.
WPP - CEO Deepfake Targeting (2024)
Fraudsters impersonated the CEO using:
AI voice cloning
Fake WhatsApp account
Deepfake video in a virtual meeting
The goal was to trick executives into financial transactions
AI-Powered Business Email Compromise (BEC) Surge in U.S. Companies (2025–2026)
Nearly 60% of U.S. companies reported increased fraud losses tied to AI (deepfakes, phishing, impersonation).
Attackers use:
AI-written emails mimicking executives
Voice cloning to “confirm” requests
These scams often target:
Wire transfers
Payroll changes
Vendor payment updates
What’s the answer?
Unless we can get better methods and technology around communication authentication, you’re going to need to train your employees in a different way. CIO’s can’t expect to push employees to simply train harder, it’s going to take more operational maturity to actually address the heightened sophistication.

Gif by cbs on Giphy
We’re at a place where AI has fundamentally changed social engineering. Attackers can now convincingly impersonate executives using voice, video, and perfectly written communications. If your job isn’t hard enough, you now have to avoid landmines that are perfectly camouflaged.
We must reduce or eliminate trust from communication channels and anchor it in verified processes.
This is how you begin to shift that trust:
No single individual can authorize a high-risk transaction.
All sensitive requests are independently verified.
Employees who challenge, instead of comply.
A compromise in one-channel doesn’t lead to misappropriations.
There’s no stopping the AI train, so we cannot just continue to train harder and think we can win. We have to operate differently and shift trust to the process layer of our operations.
One of your top defenses to AI born threat, might just be a really well run company.
Until next week,
—Jared
Text Me: 314.806.3912
How To Support Me

Let me send this directly to your inbox every week, subscribers also receive special events and downloads that I don’t publish anywhere else. I enjoy your feedback and respond to every email.
Your inbox is full. Slack is piling up. Client messages need a response yesterday. Typing thoughtful replies to all of it takes hours you don't have.
Wispr Flow turns your voice into clean, professional text you can send the moment you stop talking. Speak like you would to a colleague — tangents and all — and get polished output. Emails, Slack, LinkedIn, WhatsApp, whatever's open.
89% of messages sent with zero edits. Used by teams at OpenAI, Vercel, and Clay. Works on Mac, Windows, and iPhone.



