C-suite career advice: Jason VandeBoom, ActiveCampaign

What was the worst piece of business advice that you received? “Pick a niche. So much business advice basically boils down to ‘focus on one thing’ but if last year has taught us anything, it’s that change happens…”


Name: Jason VandeBoom

Company: ActiveCampaign

Job Title: Founder and CEO

Location: Chicago

Jason VandeBoom is the Founder and CEO of ActiveCampaign. Founded in 2003, ActiveCampaign accelerates every company’s growth with the only automation platform designed for ideal customer experiences. A lifelong entrepreneur, VandeBoom has been named to Crain’s Chicago Business 40 Under 40 list and was a 2019 Midwest finalist for EY’s Entrepreneur of the Year Award. He is a member of the Young Presidents’ Organization (YPO) and The Economic Club of Chicago. VandeBoom also serves on the board of the Future Founders Foundation, a Chicago-based organisation that empowers the next generation of business leaders and entrepreneurs.

What was the most valuable piece of career advice that you received? There are two pieces of advice I follow closely: 1) Stay close to the details, and 2) Don’t overthink what may or may not need to change for scaling over time. For example, I still dedicate time daily to reading customer feedback of our product. It helps me keep a pulse on our customers’ needs and challenges, so we can make the right decisions for them. I also know that a lot of entrepreneurs lose sleep over challenges of scaling their business. Instead, think of it as constant evolution. One of my team’s core values is “iterate everything, always,” which keeps that perspective of constantly changing in check. With that perspective, we don’t have to overthink changes for scale.

What was the worst piece of business advice that you received? Pick a niche. So much business advice basically boils down to ‘focus on one thing’ but if last year has taught us anything, it’s that change happens, and if you have a hyper-focused approach that leaves you no room to adapt, you might not have a business tomorrow.  If I had followed this advice I would never have made the pivot from on-premise software to SaaS. Ignoring the advice was also one of the driving factors behind our growth and enabled our team to be more innovative.

What advice would you give to someone starting their career in IT/tech? My advice would be to showcase what only you can bring to the table while being open to exploring and working in areas that may not directly line up with where you think you want to go. What do you offer that is unique and that will leave a lasting positive reflection on you. How can you wow the hiring manager or your cross-functional teammates? For example, recently, one of our customer support teammates made a rap about our capabilities because he was inspired. He shared that with our marketing team, and that’s one of our most-engaged posts on social media right now by our customers. Thinking about how we can add the wow factor is actually one of our core company values for this reason.

Did you always want to work in IT/tech? I always wanted to create things. Tech was just an avenue to do that. I became interested in computers when I was young and taught myself how to code, but I actually went to art school after high school. To fund my courses, I started ActiveCampaign. At that time, I noticed that a lot of small businesses had complex digital needs, but there weren’t solutions that met those needs at an affordable price. When ActiveCampaign focused on this market, we started growing organically, and then after we switched to a SaaS model focusing on customer experiences in 2016, we started growing rapidly.

What was your first job in IT/tech? I started consulting small businesses at a young age. It allowed me to understand different business needs like where these entrepreneurs were spending time, how the right tool or software could help, if they could automate a task to free up their time.

What are some common misconceptions about working in IT/tech? There’s a misconception that there’s one best city or a certain type of background that works best to succeed in tech, but that’s not true. Like any business, tech needs diversity to ensure it is fully representative. Not only is this the right thing to do, but it also makes sense financially. Better representation across gender, ethnicity, academic background, hometown and more leads to better ideas and innovation, and we can create solutions that solve more people’s challenges. At ActiveCampaign, one of our core values is to cultivate diversity and inclusion, and we have several employee resource groups like Women of AC, ActivelyBlack and ActivelyLatinx to foster mentorship and professional growth.

What tips would you give to someone aiming for a c-level position? I always encourage those around me to focus on gaining experience in a variety of roles. If you find yourself in a situation where things are somewhat ambiguous and growth is taking off, it is likely a scenario where things can be chaotic at times. Rather than trying to find the path of least chaos, use that as an opportunity to really engage within different parts of the business. Being willing to take on a new challenge or support a different team shows tremendous leadership. And, you’ll earn the trust of more cross-functional teammates, which will then open up more opportunities for you in high-impact areas.

What are your career ambitions and have you reached them yet? My career ambitions revolve around impact. Through ActiveCampaign, we’ve been able to help over 150,000 companies grow, and I want to keep supporting more businesses around the world to grow and improve their customer experiences. We are just getting started, and the continued growth and opportunity that exists within both new businesses and growing businesses is one I am proud to be part of.

Do you have a good work life balance in your current role? I have a work life balance that continues to evolve over time. Understanding that it is ever evolving just like any other skill or experience while working to ensure it works for family and myself. The important thing is to give it thought and allow times of reflection for what is or isn’t working. There is no singular or best “work life balance” that is universal across all individuals. Giving resources, time, and autonomy for people to adjust how they work, where they work, and ways we can assist whenever possible is key.

What, if anything, would you change about the route your career path has taken? I am happy with the route I have taken. Some would say I could have moved faster to the hyper growth portion of ActiveCampaign but all of the moments (even the parts that seem less exciting) all add up to where someone's career is at - and perhaps far more importantly - makes up who that person is.

Which would you recommend: A coding bootcamp or a computer science degree? I’ve always been self-taught so it’s hard for me to pick one over the other, but people need to choose what will work best for their learning style. Don’t just follow others.

How important are specific certifications? It depends on the person and business. A lot of what I’ve learned has been self-taught, but clearly there is value for certain certifications depending on the business need or an individual’s own ambition.

What are the three skills or abilities you look for in prospective candidates?  We look for candidates that can embody our company values. As a customer-first organisation, candidates who can demonstrate how they’ve gone above and beyond for their customer will always rank highly on the shortlist. Trust is also a key value for us and we also look for candidates who can wow us. We want every encounter that our customers have with ActiveCampaign to stand out as being memorable, positive and rewarding, so naturally if candidates can do the same in their interview, we know they have a long and prosperous future with us. 

What would put you off a candidate? Those who don’t embody our core values.  Basically, anyone who isn’t a team player or puts themselves over lifting up the entire team. We’re also really committed to building an inclusive, innovative community and only want candidates who are supportive of that ethos.

What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? Not doing their research on the company. We only want to hire people who understand what we’re trying to achieve and our goals for both us as a company and for our customers. You can’t say you're the best for the role, if you’ve failed to undertake basic research on what the company’s mission statement is all about. That’s why my advice is always to do your research, read the company blogs or press releases and if they offer a free trial of their product, sign up for it so you can really get under the hood of the company you hope to work for.

Do you think it is better to have technical or business skills – or a mix of both? A mix of both can be helpful. You should have enough of the technical skills to know your challenges and opportunities in regards to what is possible as well as what “innovation” would actually be, and enough business expertise to be strategic in the application of those skills.