Billtrust CFO Mark Shifke likes to label himself an “accidental CFO”—a tag that a number of our guests have appropriated from time to time when faced with explaining a past filled with less-than-traditional career experience. However, in the case of Shifke, the term arguably has little to do with career experience, for Billtrust’s CFO spent nearly a decade on Wall Street before entering the C-suite. Instead, Shifke uses the appellation to help to reveal the pivotal role that a single phone call came to play in his finance career. Back in 2000—near the beginning of Shifke’s Wall Street career and the end of the market frenzy known as the dotcom bubble—Shifke took a phone call from a CEO founder whom he had met through a personal acquaintance. Just as the CEO didn’t hesitate to ask Shifke to invest in his struggling company, Shifke didn’t dither when it came to coming up with some figurative cash. “I made a handshake agreement with him over the phone,” explains Shifke, who notes that the investment did require some visibility into the company’s sales pipeline.   “I told him, ‘If you are successful at selling into this environment and you are able to generate revenue, then on the back of that, I will raise capital’—and I did so,” recalls Shifke, who raised a "family and friends" round of funds that allowed him to become a central angel investor in the company Green Dot Corp., a fintech start-up and pioneer of prepaid debit cards.   Fast-forward 11 years, and Shifke is no longer just a Green Dot investor but a board member, when he opts out of a managing director role at JPMorgan Chase to join Green Dot in a senior corporate development role.  “It’s one thing to invest in a business and it’s another to advise a business, but it’s quite another thing to go operate it—and I had never operated one,” comments Shifke, who would enter the CFO office at Green Dot a few years later in 2015. In the end, Shifke says, the “accidental CFO” label still fits because he originally had zero aspirations to be a CFO and now-midsize fintech firm Green Dot simply became the means to scratch his operations itch.    Says Shifke: “There was an opportunity to either enhance my position as a shareholder or materially harm it—but this tended to play out to the positive.” –Jack Sweeney  Leave rating & review   Signup for our Newsletter GET MORE: Order now The CFO Yearbook, 2021