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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 \u201cinsight\u201d into the company\u2019s future.

\u201cThe CEO really wants to take this company public, this is probably never going to happen\u2014we\u2019ll likely sell in the next couple of years,\u201d Hudson recalls the CFO remarking, before he added: \u201cUsually, finance people don\u2019t stay in the event that a company is sold\u2014we just leave and go on to the next one.\u201d

At the time, Hudson says, she didn\u2019t know what to make of the CFO\u2019s 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.

\u201cIt was a much longer journey, but we did end up there,\u201d 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\u2019s 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.

\u201cThe path was definitely not always certain, and there were moments when you would reassess,\u201d comments Hudson, who remembers receiving a challenging international operations assignment from a newly hired CFO\u2014and doubting whether her experience was a good match.

\u201cMy sense at the time was \u2018I don\u2019t think that I can do this, I don\u2019t even know if I want to do this, I think I\u2019m done here,\u201d 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\u2019s clear that the previous CFO perhaps was misjudging the firm\u2019s 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 \u201cgo on to the next one.\u201d\xa0\u2013Jack Sweeney\xa0