Odd, outrageous, and downright silly reimbursement requests

We know the job of CFO is sometimes not the most glamorous: the image of the bean counter, number cruncher, the one who says “no” to anything fun is not always fair or accurate.

So we decided to seek out something under the purview of the finance team that might have universal appeal: expense reports.

Jennifer Elder, owner and CEO of consulting and executive coaching firm The Sustainable CFO, said there’s good news about expense reports for CFOs and accountants: “It’s getting a lot easier thanks to AI and expense reporting technology.”

And yes, the sales team is still typically the department that files the highest volume of expense reports, she added.

Elder believes that most employees who try to submit unusual expense requests usually fall into two categories: those who believe they are underpaid and may be seeking shortcuts to earning more money, and senior executives convinced that they’re unstoppable.

But, Elder notes, expense reporting software companies give companies the ability to more closely scrutinize expenses in a shorter period of time. “AI can catch so much more fraud than we ever could with our traditional controls,” Elder told CFO Brew.

Matt Allen, head of receipt integrations at workplace software firm Expensify, compared the shift from handwritten or typed expense reports to automated reports as akin to trying to skip school as a kid: A generation or two ago, you might get away with it in the short term, but you’d eventually get caught. Now, you’re more likely to not get away with it at all.

“Parents get texts or emails that ‘Your kid wasn't in class 15 minutes ago,’” he noted. With expenses, “you used to be able to get away with much more because it was pieces of paper in manila envelopes and [a] stapled receipt,” Allen told CFO Brew.

He added he doesn’t necessarily think every errant expense report is someone trying to take advantage of their company. Trying to expense a costume from a company costume party might just be a matter of misunderstanding.

“Is their intent to try to sneak in an expense?” he mused. “I could totally see that being legit in somebody’s mind.” Often when called out in these circumstances, the person would probably just apologize, Allen said. “I think honestly a lot of the stuff that happens that we see is more mistakes,” not people trying to put one over on the company.

We asked CFO Brew readers to share the most bizarre expenses ever requested or approved. And you didn't disappoint.

We received dozens of replies pointing to at least one mini-trend: Some of you are out here in these streets (literally) asking your companies to reimburse you for speeding tickets. (We don’t endorse such behavior, to be clear, but one can almost see the argument.)

• Abigail T. approved an employee’s request for Miracle-Gro for their office plant.
• Mark S. said an executive at his company offered to host a team-building exercise at her home, but then submitted an expense report for a brand-new patio set and gas grill. The request was denied.
• Stacie B. declined a traffic ticket for an illegal U-turn during a conference, doggie daycare, and a “VERY expensive movie charge” on a hotel bill, but the charges were ultimately approved by a manager.
• Sarah D. was approved for paddle-boarding in Miami because the clients weren’t fond of late nights or excessive drinking.
• Victoria L. approved a CEO’s blue lobster costume, worn while he got a pie to the face after losing a bet.
• Peter G. approved a new iPhone after a monkey stole one from a member of his staff.

As for Allen’s own most unusual expense item? A last-minute tattoo of a discontinued Expensify logo on a company-sponsored trip to Quebec.

“Other people wanted them but the local tattoo ship ended up being booked all week,” Allen said. “I went on Tuesday morning to request an appointment later in the week and they said the only opening they had was now, so I took it.”

His expense was approved.—LR