He’d built up his career at places like FLEETCOR, ADP, and IBM, and had been part of selling into successful enterprise organizations. So McCrossan recognized that those logos were a clear sign that Oversight had built up serious traction in the fintech space.
That first impression at the office marked the beginning of what he calls “the role of a lifetime.” Oversight named McCrossan CEO in 2018, and he now leads a company that helps enterprises manage a growing volume of financial transactions flowing through their systems every day.
“Oversight wasn’t the first company that I vetted in terms of potentially taking a role like this, but it was the first one that I felt was just a terrific fit,” he says. “Good fortune and good timing.”
Solving Enterprise Finance Problems
Oversight has long been part of Atlanta’s technology ecosystem. The company has been building for the last 22 years, coming out of Georgia Tech’s ATDC accelerator program under the leadership of Patrick Taylor (who served as the company’s CEO from 2003 to 2018).
McCrossan, who has served as CEO since 2018, is leading Oversight as its client list has grown to include Delta, Caterpillar, GE Appliances, Carrier, International Paper, Texas A&M, and many more.
“The typical enterprise we’re working with has usually tens of thousands, if not hundreds of thousands, of expense reports or expense purchases submitted by employees,” McCrossan explains. “Attached to those expense reports are typically millions of receipts, and buried in those receipts are typically tens of millions of transactions.”
The traditional manual review process simply can’t keep up with the mass of financial information that every company creates. Oversight’s spend monitoring platform automates the entire process, applying AI to identify what’s worth examining and providing auditors with streamlined workflows to take action.
The result? CFOs gain significantly more confidence that dollars leaving the business are going to rightful purposes.
The team most recently launched its Receipt Analytics solution, what they say is a “first-to-market) fake receipt detection analysis tool. This can help companies with expense receipt auditing and “stay ahead in an evolving risk landscape” in a way not capable by OCR (optical character recognition)-based detection approaches.
The innovation emerged from Oversight’s dedicated Innovation Lab, achieving over 90% accuracy in detecting fraudulent and AI-generated receipts while reducing false positives by 80% compared to traditional OCR-based systems.
Leading In The AI Age
McCrossan told Hypepotamus that Oversight has been “AI since our foundation,” even before the term was ubiquitous in the tech world.
“We don’t index on any one particular AI method as the answer to the equation,” he explained. “We use everything from expert systems to large language models to machine learning and certainly agentic being a big piece of the forward looking picture.”
It is the rapid evolution of AI technology that does keep CEO McCrossan up at night.
“The technology evolution, particularly with continuing acceleration on the AI side, is something that we have to constantly be conscious of in terms of how we innovate and deliver rapid advances into our client base.”
But what energizes him is the team he’s built to meet that challenge.
“We’ve attracted just enormously good people to our business, folks that are unbelievably dedicated to what we’re trying to do, incredibly committed to our clients and have a passion for trying to make Oversight a better business.”
That team operates under a “work where you work best” policy, with a largely virtual workforce. That approach McCrossan credits as key to attracting and retaining top talent.
He also believes that Oversight’s biggest opportunities lie ahead.
“As much success as Oversight has had to date, I still view the majority of the growth and opportunity for the business that’s still in front of us, and that’s a good place to be,” he added. “I’m looking forward to Oversight being a significant brand and a significant technology player in the financial landscape for a very long time, and I think we’ve got a good foundation to achieve that, but we’re still just getting going.”