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.Read More
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 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.
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.
“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
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CFOTL: Tell us about this company … what does it do, and what are its offerings?
Hudson: EngageSmart is a software company. We simplify client and customer engagement. What this really means is that our solutions just make it easier for people to do business. 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.
One thing that’s pretty unique about EngageSmart is that we have an inverted pyramid structure. It’s very much a servant–leader type organization. Customers and their clients are at the top of our organization, and they’re at the center of all of our priorities and how we make decisions. We’re really making decisions with this end user in mind, with the goal of just making their life easier. When we encounter a difficult user experience, we think, “Why is this so hard?” That’s an EngageSmart opportunity for sure.Read More
I joined EngageSmart a little over a year ago, and obviously I was incredibly impressed by the financial profile of the business.
We’ve spent a lot of time this year in putting the right people into place. The next phase will be about evolving our processes to support a much larger organization. To me, automation is key. Providing information at a very detailed level in real time is another area in which we plan to invest and make a lot of progress in terms of our understanding of the business, KPIs, and how we get this information in the hands of the right people across the company.
Apart from this, it’s really telling the financial story of EngageSmart. Being a newly public company, I think there is a lot that people that still need to learn about us, and finance needs to help even our own employees to understand what it means to be a public company and this will be a big area of focus for me in the coming year.
EngageSmart | www.engagesmart.com | Braintree, MA