Back in 2008, Cassandra Hudson was interviewing for a senior accounting role at a small tech firm in Boston when the CFO casually shared some “insight” into the company’s future. “The CEO really wants to take this company public, this is probably never going to happen—we’ll likely sell in the next couple of years,” Hudson recalls the CFO remarking, before he added: “Usually, finance people don’t stay in the event that a company is sold—we just leave and go on to the next one.” At the time, Hudson says, she didn’t know what to make of the CFO’s comments, especially when they accompanied a job offer. One IPO and multiple CFOs later, the Boston tech firm was sold to developer OpenText in late 2019 for $1.4 billion. “It was a much longer journey, but we did end up there,” reports Hudson, who in 2020 stepped into her first CFO role as the culmination to a remarkably linear 15-year career path at the Boston tech firm, which itself grew from less than $10 million to more than $400 million in annual revenue during Hudson’s years on board. Today, as CFO of EngageSmart, Hudson looks back at the succession of promotions and job titles and experiences that have punctuated her climb upward to senior management and the merits of making a 15-year career investment within a single company. “The path was definitely not always certain, and there were moments when you would reassess,” comments Hudson, who remembers receiving a challenging international operations assignment from a newly hired CFO—and doubting whether her experience was a good match. “My sense at the time was ‘I don’t think that I can do this, I don’t even know if I want to do this, I think I’m done here,” explains Hudson, who adds that the CFO reassured her that she had all of what was required to complete the assignment. Today, looking back at her job interview at the Boston tech firm, it’s clear that the previous CFO perhaps was misjudging the firm’s IPO prospects, dogged future growth trajectory, and ultimate sale timing. Still, he did mention that there would come a day when it would be time to “go on to the next one.” –Jack Sweeney