It’s very much a servant–leader type organization. One thing that’s pretty unique about EngageSmart is that we have an inverted pyramid structure. We do things like make it easier for people to make a charitable donation through electronic means, to pay bills online, to schedule an appointment, to run the entire business side of a physical or mental wellness practice as a healthcare provider. What this really means is that our solutions just make it easier for people to do business. We simplify client and customer engagement. Hudson: EngageSmart is a software company. Still, he did mention that there would come a day when it would be time to “go on to the next one.” –Jack SweeneyĬFOTL: Tell us about this company … what does it do, and what are its offerings? 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. “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. “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. 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 12-year career investment within a single company. “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 12-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. One IPO and multiple CFOs later, the Boston tech firm was sold to developer OpenText in late 2019 for $1.4 billion.