It was 2018, and shortly after payables start-up Tipalti had raised its Series C funding round, Sara Spoja recalls, she sat down with Tipalti CEO and cofounder Chen Amit. Having spent the previous 8 years as a senior operating executive for private equity firm KKR Capstone, Spoja was known for asking C-suite management tough questions, and she was no less probing when it came time to reviewing Tipalti’s Series C model. “I tore that thing apart and asked questions about every assumption,” comments Spoja, who recollects a 4-hour-long meeting with Amit, who encouraged her to grill him on every aspect of the business. During the meeting, Spoja no doubt turned over as many rocks as any of Tipalti’s Series C investors had, but Amit wasn’t looking for an investment from KKR. Indeed, he wanted an investment from Spoja—but not in dollars. Tipalti had achieved the requisite number of start-up milestones that normally precipitate the hiring of a chief financial officer, and it turned out that Spoja had quickly advanced as the tech firm’s leading candidate. “I had hit a patch at KKR where I wasn’t as excited as I might have been about what my next role was going to be,” remembers Spoja, whose seat on KKR’s operating executive talent bench had in the past propelled her into a rotating variety of portfolio company operational roles—each with an expiration date. “I decided that it was time to go and take my first real job at a company,” reports Spoja, who would join Tipalti as CFO in August of 2018. –Jack Sweeney