Freddy Massimi, Fraud Analytics Analyst at Live Oak Bank and certified human trafficking investigator, shares how AI-generated document fraud is changing financial crime, and why fraud teams need to look beyond the transaction.
I sat down with Freddy Massimi at Fraud Fight Club Round 3, where he was representing Live Oak Bank as a Fraud Analytics Analyst. He also collaborates with The Knoble — a global nonprofit network of financial crime professionals fighting human trafficking, scams, and exploitation — and DeliverFund, a counterterrorism-methodology-driven organization that equips law enforcement to take down human traffickers.
His career path, from third-shift debit card fraud to human trafficking investigations to AI-generated document detection, maps the full arc of where financial crime and human harm intersect.
He's also an Inscribe customer, and his passion for fighting fraud was palpable at the conference.
Massimi started in fraud in 2012 on the third shift at BB&T, handling debit card fraud calls. The transaction volume was high; what held his attention was the pattern beneath it. That pattern eventually led him to human trafficking — specifically, to the financial signals that precede or accompany exploitation: transaction flows through hotels, airlines, Airbnbs, and VRBOs that, when analyzed, indicate activity that law enforcement hasn't yet reached.
He pursued certification as a human trafficking investigator to establish standing as a subject matter expert in a field that was still taking shape. The certification has since become more widely recognized as financial institutions have increased their focus on the intersection of financial crime and exploitation.
At Live Oak Bank, Massimi uses Inscribe to flag AI-generated documents (pay stubs, driver's licenses, bank statements) that would otherwise clear manual review. The barrier to entry for document fraud has dropped significantly: convincing forgeries are available for as little as $10. "Fraudsters are always five steps ahead," he said. "Inscribe does a really good job of catching what humans miss."
The case that reframed how he thinks about the job came from his time as a vulnerable adult investigator at Truist. A pig butchering scam victim called in. She told him: "If you didn't call me today, I was going to commit suicide." He contacted law enforcement immediately. Officers found her alone and in serious distress. "No matter what role you play," he said, "trust your gut and treat that customer like your grandparent."
I’m looking forward to having Freddy back for a longer conversation on a future episode of Good Question. There’s a lot more ground to cover.
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Brianna Valleskey is the Head of Marketing at Inscribe AI. A former journalist and longtime B2B marketing leader, Brianna is the creator and host of Good Question, where she brings together experts at the intersection of fraud, fintech, and AI. She’s passionate about making technical topics accessible and inspiring the next generation of risk leaders, and was named 2022 Experimental Marketer of the Year and one of the 2023 Top 50 Woman in Content.
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