Cassandra Hudson Of EngageSmart: 5 Things I Wish Someone Told Me Before I Became a C-Suite Executive
Don’t get too caught up in your successes or your failures. Stay focused on what you are trying to achieve, learn along the way and try and have fun in the process.
As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company” I had the pleasure of interviewing Cassandra Hudson.
Cassandra joined EngageSmart in 2020 and serves as the company’s CFO. She most recently served as the Chief Accounting Officer and VP of Finance for Carbonite, Inc., which was sold to OpenText in December 2019, where she had direct responsibility for all aspects of the corporate finance function including FP&A, accounting, revenue operations, internal audit, tax and treasury. She is a results-driven corporate finance executive with deep experience in building, leading and advising companies through rapid growth, capital markets transactions, international expansion and M&A activity. Cassandra lives in Lakeville, MA with her husband and two children and enjoys running in her free time.
Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
I’ve known what kind of career I wanted to have since I was in eighth grade — that’s when I started researching business schools. I knew it was my calling. I took an accounting class in high school, but I thought accountants were boring and didn’t think it would fit my personality, so I continued researching other business majors. I went to Bentley College and the trend of exploration within the realm of a business career continued. I jumped majors multiple times: I was a marketing major, I was an economics major. And then I finally settled on finance and accounting, because it came naturally to me, and many of my professors were encouraging me to pursue a public accounting career. After college I joined a regional public accounting firm in Boston where I worked for about two years. I left because I wanted to get my MBA and shift to a broader business role. For most of my career, the roles that I’ve had — outside of my first public accounting role — have been very broad. That said, building a foundation in public accounting has been very beneficial to the rest of my career so I’m very thankful for being pushed in that direction. I’ve always been more of a generalist, less of a specialist. I’m not sure many people can relate to always knowing what you wanted to do, in a broader sense at least, but I was lucky, this is what comes naturally to me and it’s also what I love.
Can you share the most interesting story that happened to you since you started your career?
My last company was on the going-public track, and obviously an IPO is an involved process where things can go wrong every step of the way. But for us, we kind of sailed through the process; I was surprised the entire time by how smooth it was. And then when we went on the road to sell the IPO to public company investors, the stock market was volatile to say the least — this was the US debt crisis in 2011. There were 85 companies on the road trying to go public, and only two got out. The final day of our roadshow, we had several meetings and our board decided to call off the IPO. It was the culmination of years of work, and at the very last minute it was like, “forget it.” So I went home completely defeated, and then I got a phone call at eight o’clock at night that the board had changed their mind, we’re going public. And so I basically took the company public from my couch. But I was so glad to have gotten there.
Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?
One of my guiding principles is: Not my circus, not my monkeys. It basically means you can’t do everything, and sometimes it’s wise to hang back and let experts control their “monkeys” while you focus on what you know. For example, there was a leadership meeting earlier this week, and the topic was something that I didn’t really feel like I was an expert in. It just wasn’t my area. So I just listened to what everyone had to say. I think it’s kind of important to play your position, to act when you can and listen when you can’t. You can drive yourself crazy by trying to worry about everyone else and what they’re doing. You know, I think it’s really important to stay very focused on what you’re doing and trying to achieve and trust that the rest of your team is doing the same.
Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?
Not necessarily a particular book that’s influenced my leadership style, but I think I’ve been pretty influenced by people that I’ve worked with in my career, and people that I look up to. There are a couple other CFOs I’ve considered mentors that have made a huge impact on the direction of my career. And there are people today that I still call for advice. I think mentorship is interesting. It’s not always an intentional thing. If you were to ask these people, they wouldn’t know that I consider them my mentors. It’s just something that happens naturally, but that’s had a big impact on me personally.
What do you think makes your company stand out? Can you share a story?
Our culture is unique. It’s a servant-leadership, where customers and employees are at the top of the organization and management is at the bottom. It was something new for me when I joined last year, certainly. But I’ve come to really value it. And you feel it day-to-day in how we operate. I think that gives us an edge.
Also, we’ve been very balanced in terms of revenue growth and profitability, which is also pretty unique. Not a lot of companies out there have this level of discipline from a financial perspective.
The road to success is hard and requires tremendous dedication. This question is obviously a big one, but what advice would you give to a young person who aspires to follow in your footsteps and emulate your success?
You’re gonna fail a hundred times — if not a thousand. And those are the moments that you should be thankful for. Failure is where you learn and grow. And I know it sounds terribly cliche, but all that matters is that you keep going. There have been so many times in my career when things haven’t gone the way I wanted, but in hindsight all of those things were absolutely for the best. And all that matters is that you work as hard as you can and do the best you can every day.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
I actually tend not to listen to advice. I’m a very independent thinker, so if I’m going to follow someone’s advice, I really have to believe it and trust it at my core. For instance, I haven’t received much negative pushback about the fact that I’m a working mom. Quite the contrary — I’ve had nothing but opportunity. But early on in my career, after I started having kids, I did have a boss that indicated that I should slow down and focus on either my family or on my career, that I couldn’t handle both. And stuff like that shakes your confidence, right? You might hear that and start to believe it. Someone else, maybe someone with more experience is giving their opinion and it can feel like “Well, what do I know? I’m a new mom in a really challenging career.” Well, I didn’t listen to my boss’s advice, and I’m really glad I didn’t, because it did all work out. It was certainly chaos for years, when I was trying to figure out how to be a mom and have a really important job. But this is what I’m meant to do. I wouldn’t have it any other way.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
- I’m relentless. I’m able to persevere during challenging and stressful situations, and I can handle difficult people. This doesn’t mean I don’t get frustrated in the moment, it just means I will never give up — even when I probably should. I think the key is that I can stay focused in a difficult situation and then wake up the next day and think of an entirely new way to attack it. That ability to develop a fresh perspective has served me well a hundred times over. You’re always going to encounter frustrations and road bumps and things that make you feel like you should give up — and almost 100% of the time you’re gonna be glad you saw those moments through.
- I’m not very sensitive, so I tend to not take things too personally. I understand that I’m here to do my job, and I also like to have fun with my team. But if something doesn’t go my way, even something I feel strongly about, I have a pretty good ability to say to myself, “Okay, well, I can get on board with the alternative.” I can separate myself from what I’m trying to achieve from a business perspective, and that has been essential.
- I like to have fun. I think CFOs tend to have more reserved and serious personalities, but that’s not who I am at my core, and I think people tend to be surprised by that. I tell crazy stories, I laugh. At the end of the day we’re all just people, and life is all about connections and building good relationships. I’ve been able to build amazing finance teams that stick together and love working together, because the people I work with are incredibly important to me on a personal level.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words can you explain what a C-Level executive does that is different from the responsibilities of other leaders?
I think, to me, the big difference is the role of communication. A C-suite executive is really there to set the direction, and to manage and build teams, of course. But other leaders have team-building responsibilities as well. The difference is really in the degree of communication you have to employ in the C-suite and especially as the CFO. That was a really big change for me, to really just focus on being the primary communicator for the financial function of the company with many different stakeholders including employees, our Board of Directors, investors and the analyst community.
What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?
I think there’s a misconception that people at the C-suite level don’t care about the employees or the broader organization — but that’s all we ever think about. The success of the business and the company, and the success of all the people for whom we’re responsible and whom we impact. That’s what we’re really here for, that’s what’s driving all the decisions that we’re making.
What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?
I’m still in the mistake-making phase. I’m definitely not perfect and still learning, but that’s part of this. How boring would it be if you had all the answers? I think one of the most important elements is understanding the influence of the position. My attendance at a meeting, or my speaking up at a meeting, carries more weight than it did before I was in the C-suite. It can change the direction of where we’re going. And I’m not used to that. I love sitting in a meeting and brainstorming, but I’m realizing that in those kinds of settings, I actually have to be very quiet. Even what I think of as a casual observation can change the group’s momentum, or my presence can cause a person to keep quiet because they’re worried that I, as CFO, will think their idea is too expensive. So I’m still learning this lesson that I have to hold back and allow all the different ideas to surface.
In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?
Running a company is hard, and there are a lot of complexities that people don’t understand. Things can be so much more related than people realize. One decision can impact five others. It’s actually something I love about my position: having that big picture view. I think people have a misconception that in the modern world, everything is immediate and instantaneous. But it’s a lot of work to create those simple, instantaneous modern experiences. I don’t think people realize what goes into keeping a business growing and scaling at this level. EngageSmart has experienced tremendous growth, not a lot of companies achieve growth like this. And in order to continue to grow, you hit a point where the processes you’ve been using to run the company no longer work, and you literally have to rip out the jet engine of the airplane while it’s flying to build something new over and over and over again, because the company is doubling, tripling, quadrupling in size.
Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading From the C-Suite”? Please share a story or an example for each.
- Communication is critical. It’s going to become 95% of your job, whether between your team and the wider company, or investors, or the board, or regulators, or any combination thereof. That is the whole job. That’s a big change, and it’s absolutely critical.
- Try to be humble. You may feel like you’re still a regular person, but others may not see you that way anymore. You can’t control how other people feel around you, but it can influence and impact things and change your day-to-day as a result — and you have to be okay with that. As a C-suite executive, you do have more power, and you can’t trick people into thinking you don’t, even if that’s how you want to be seen.
- Imposter syndrome is a real thing. When you make the transition to the C-suite, even the most confident among us might think “Am I good enough? Can I do this? Am I gonna mess up?” Everyone feels this way.
- Remember that despite how intimidating all the above may sound, you’re ready. The title can feel intimidating, but the job isn’t that different from what you’ve been doing your entire career, even if you’re rotating a bit more towards communicating with a wider audience. But your career has prepared you for this.
- Don’t get too caught up in your successes or your failures. Stay focused on what you are trying to achieve, learn along the way and try and have fun in the process.
In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?
I remember when I interviewed for this job, Bob talked about how unique the culture was, and how important it was. And I remember thinking — and he would be horrified by the statement — that my number one attraction to the business was the financial profile and how well-run the company was. Honestly, that was what brought me to the team. And so when he was really pushing on the culture, I was like, “Yeah, I can work with lots of different types of people, lots of different types of cultures. For me, it’s just not necessarily the most important factor in where I’m going to go.” But when I got here, I really understood what he meant. The culture here is special.
And it shows itself in the small things. When people here know you’ve had a hard day, they are likely to have some treat delivered to your house when you get home. Or when it’s a birthday, extra care is paid to what that person would enjoy. (When it was my birthday, for example, I was shocked by all the small touches put in place and how celebratory everyone was.) Bob, the CEO, focuses a lot on how he can help solve problems for and with everyone across the company. His humility and support for everyone’s autonomy goes a long way to create our exceptionally positive work environment. Everyone really goes the extra mile here.
Even having a boss who hates that you’re doing work on vacation, instead of rewarding that behavior. It’s different for me, and that’s what makes this a great place to work.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)
Personally, I think people would benefit from less social media. It concerns me that people are blindly believing everything they see and read online. I’m afraid people are losing their ability to think logically and independently, and I’m especially concerned by the impact it has on our younger generations.
How can our readers further follow you online?
Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!
