Navigating the Challenges of Scaling

Navigating the Challenges of Scaling written by John Jantsch read more at Duct Tape Marketing

The Duct Tape Marketing Podcast with John Jantsch In this episode of the Duct Tape Marketing Podcast, I interviewed Jason, the CEO of ActiveCampaign, a leading platform for intelligent marketing automation. A lifelong entrepreneur, Jason has been named to Crain’s Chicago Business 40 Under 40 list and was named EY’s Entrepreneur of the Year Midwest. […]

Navigating the Challenges of Scaling written by John Jantsch read more at Duct Tape Marketing

The Duct Tape Marketing Podcast with John Jantsch

In this episode of the Duct Tape Marketing Podcast, I interviewed Jason, the CEO of ActiveCampaign, a leading platform for intelligent marketing automation.

A lifelong entrepreneur, Jason has been named to Crain’s Chicago Business 40 Under 40 list and was named EY’s Entrepreneur of the Year Midwest. He is a member of the Young Presidents’ Organization (YPO) and The Economic Club of Chicago. Jason also serves on the board of the Future Founders Foundation, a Chicago-based organization that empowers the next generation of business leaders and entrepreneurs. He is also a regular contributor to Fast Company and Forbes.

Having founded ActiveCampaign as a means to fund his education, Jason pursued a degree in fine arts until shifting his focus entirely to growing the company. He is a self-taught software engineer and technologist. Our conversation dives deep into the challenges that businesses face when scaling up, offering valuable insights and strategies for navigating this crucial phase of growth.

Key Takeaways

Jason emphasizes the importance of maintaining customer focus, embracing change, learning from failure, building a strong team, and staying true to your values when scaling a business. By prioritizing direct interaction with customers, fostering a culture of innovation, viewing setbacks as learning opportunities, investing in employee development, and upholding integrity and ethical conduct, businesses can navigate the challenges of growth and achieve sustainable success.

Questions I ask Jason Vandeboom:

[01:02] Is there a reason why ActiveCampaign was decided to focus specifically on small to mid-sized businesses?

[02:33] Have you been able to keep that self-taught view in the value system and culture of your company?

[03:52] How has your personal life changed since running such a demanding business?

[05:10] When it comes to failures do you have any business advice for people starting out?

[07:37] Do you have a management philosophy as a first-time manager of people and teams ?

[09:10] How do you make decisions about how to innovate?

[12:10] What are you hoping to communicate in positioning yourself as the marketing automation CRM of small teams powering big businesses?

[13:40] What role does AI play in your road map as a leader?

[14:52] Is it an oversimplification to say it’s just better lead scoring?

[15:54] Describe the Leap Year special event ActiveCampaign is organizing?

[17:57] What’s your secret to never getting bored with what you do as a CEO?

[20:16] What’s on your bucket list in the next 5-10 years, outside of work?




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This episode of The Duct Tape Marketing Podcast is brought to you by ActiveCampaign

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John (00:08): Hello and welcome to another episode of the Duct Tape Marketing Podcast. This is John Jantsch. My guest today is Jason Vandeboom. He is the founder and CEO of ActiveCampaign. Founded in 2003, ActiveCampaign helps small teams power big businesses with the must have platform for intelligent marketing automation. Today, ActiveCampaign is the market leader in intelligence driven marketing automation with customers in over 170 countries leveraging the platform to grow their business. He’s also a regular contributor to fast company in Forbes. Having founded active campaign as a means to fund his education, Jason pursued a degree in fine arts until shifting his focus entirely to growing the company and his self-taught software engineer and technologist. So Jason, welcome back to the show.

Jason (00:57): Yeah, thanks for having me. Looking forward to chatting.

John (01:00): So this is at least your third time on the show, and I think we were laughing about it off air that the company was just a couple of years old now. It’s obviously grown in many ways, so it’s really been fun to watch and really be a small, very small part of that growth. ActiveCampaign is very focused on small, mid-sized businesses, SMB market, which a lot of the bigger tech companies kind of ignore for enterprise. Is there any reason that you said no, we’re going to go after that segment and focus on it?

Jason (01:32): Yeah, I think there’s the couple of things. One, just a big believer in this idea of over-delivering on value, and if I think of how do you do that or who can you serve and do that the most, it’s a small team. It’s that individual marketer, small team of marketers looking to do more. It’s almost being that additional team member within that company. One of the most impactful things that I’ve found at least building a business is just the impact. If you can see the impact you’re having on brands throughout the world and on the teams themselves and whatnot, that’s the thing that drives not just myself personally, but selfishly that drives my team as well, right? Because doing something, you can see that immediate impact and so I think that’s part of the reason for it. And then also I think there’s just a huge opportunity and need to help that part of the market. All too often I think people look at that as hard to serve larger companies, that’s fine for them, but there’s a real need opportunity and it’s a challenge, which is exciting.

John (02:33): Yeah. So I mentioned in the intro that you have customers in over 170 countries today, but you essentially were bootstrapped in the very beginning. It sounded like self-taught, which means you were making it up as you were probably going that kind of scrappy mentality. Have you been able to keep that in the culture and the values?

Jason (02:54): I think it’s challenging as you scale, because as you scale, all of a sudden it becomes more about, success can be sometimes function role, you start to get further and further away from the actual customer. And so I think the key for me is how do we keep everyone as close to the customer as possible? If I’m not talking to a customer, if I’m not directly interfacing with the customer in a given week, I’m just going to get farther and farther away myself. How to replicate that across lots of people, across lots of departments, lots of teams, certainly a challenge, but I think it’s easier when you’re focused on so many interesting brands that we work with. And you can take these stories, you can bring customers to meet the team. It’s like the purpose behind what you do is something I think people don’t always focus enough on. And that purpose can be very motivating. It can be kind of a rallying cry. It can help drive what you’re looking to do as a business itself

John (03:52): Personally, how has your life changed? You didn’t have kids when you started this company, you’re now the CEO of really a leader in a very large industry. What’s that done to, I don’t know, work-life balance? I hate that term, but what’s that done to? How have you maintained sanity? Let’s put it that way.

Jason (04:10): Yeah, I think it’s changed, right? And I think the only just embracing just constant change. I think that’s what makes it exciting. If there was a moment where I thought I had it all figured out, if there’s a moment where there’s not something new to try to solve for, then it’s kind a boring operating model in my mind. And so I think it’s building team, but it’s building team and keeping them close to that customer experience, close to the customer and ultimately having to focus on different things over time. But it’s not up to any single individual, but having the right people, building the right team, having the focus to the customer, to the problem that’s being solved, that’s where I put a lot of my time and energy, which is very different than earlier on where it would be actually writing code or doing something.

John (05:03): So a lot of times when people look at companies that have really been very successful or at least certainly outwardly appear that to them, we don’t have all the behind the scenes. Are there any kind of personal or business failures where you went, well, hopefully we learned something from that, but that was a disaster? Anything along the way that I think it’s actually helpful for people to hear that when they’re growing a business?

Jason (05:28): No, I think there’s, it’s just a countless running list of maybe not, I don’t want to call ’em all disasters, but of these learning moments. But I think to your point, I think it’s the most helpful thing to embrace that. And then so one thing I like to do is I like to surface If we’re doing a company update, if I do weekly emails to the entire company, try to surface obviously the wins and the positives and stuff like that, but also try to surface and celebrate. We tried this thing, we all rally behind it, total failure. Cool. We realize that success in itself and keep moving. That’s really hard to get people to be able to embrace it though, because oftentimes through our work there’s a very personal attachment to a lot of the work. And so failure is not even thought of as we didn’t do something right business wise, but it’s like people take that on as their personal connection.

(06:23): We spend so much time working, we spend so much time in this work atmosphere, so it makes sense, but I think it’s this, you have to both as an individual, but then try to get others to identify failure, call it out in not a terrible way, but just if we can call it out quickly, that’s success. To just build this idea of iteration. And that’s something that’s always been obsessed with is just how do you just continually iterate and find these little moments of progression. When I think of failure moments that stand out, it’s like when we get too locked into an idea, we want to do something, maybe it’s a marketing type of campaign, maybe it’s a certain type of product offering and we’re like, we’re going to do this, and we just get locked in. We get blinded to the reality of we different data points, different things that are showing us maybe it’s not the right move or the customers are not responding to it, partners utilizing people that have a different view into your business. If you don’t listen there, that’s when you’re going to just start to extend that time duration of spending time on something that isn’t value add. And that’s when it moves from failure is kind of a good thing. Realize it to you just wasted a bunch of time.

John (07:38): A lot of startup founders have to actually learn to be managers sometimes have never managed people and certainly have never managed managers of people. I mean, is there any kind of one people management philosophy that you swear by

Jason (07:52): Not a singular philosophy or framework that’s out there? I think everyone is learning in their own way. One thing that I didn’t do a lot of early on was just reach out to other people thinking that they wouldn’t want to actually share or they wouldn’t share a reality. What I found is it’s quite the opposite, both when it comes from founder to founder, but then also different functional roles. There is a people that have gone through different experiences of learning going from not managing anyone, demand your managers, to your point, there’s all sorts of trials and celebration, all sorts of failure, all sorts of interesting pieces. And so to learn from others in addition to just constantly pushing yourself, I think that’s really the only way of doing it. And then the only other piece is just having that comfort level with people that you work with to be able to give really direct continual feedback versus holding in a thought to an annual cycle or something like that.

John (08:54): I’ve had a fellow Chicago on the show, Jason Freed founder of Basecamp, and one of their philosophies was, you don’t build features in just because people ask for ’em, but I’m sure you feel pressure all the time. People are wanting just make it do this little thing or do that little thing. How do you make decisions about how to innovate?

Jason (09:14): It has to be guided. So customer feedback is so important. Partner feedback is so important. It helps guide the themes of where you should focus, but if you do it exactly how someone is describing it, it’s probably been done before. You’re going to lack innovation by the very fact of it’s trying to replicate something, right? So to try to get to that root cause of what is actually trying to be solved, how can we do it a little bit differently? And then also to your point, how do you not actually feel compelled to do what someone is asking? And that is not easy. We had a situation once years ago and we had a potential deal that would’ve been a million dollar plus type of contract type of deal. It was just like they’re just going to take a quarter or two of our roadmap, so get certain things and it was this real testing moment of the team was playing.

(10:09): It would be nice to have some of the stuff actually kind of like we want to do anyway, but they want to do it in such a specific way that we think it would actually be muted in value for 80% of the population. And if we’re starting to think of something is not valuable for a material portion of the customer partner base, then that’s a distraction. It could be the short-term win, but long-term, we’re probably not going to appreciate it in that situation. We actually chose to not pursue and not go forward with that opportunity. Probably looking back at it, the right call in the moment, painful, sad, kind of happy we made the right call. So promotions.

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John (12:09): Yeah, awesome. So you’ve recently leaned into positioning, obviously marketing automation, CRM still, but small teams powering big businesses. What are you hoping to really communicate through that?

Jason (12:22): So we’ve always been about how do you unlock more, how do you allow that individual or that team of marketers to be able to do more With the idea that we’re doing a lot of the feature function, we’re doing a lot of the execution of work, we’re trying to tap into the genius of the marketer and try to extend that, right? And so we’ve always been trying to describe ourselves of we’re SMB friendly, we’re helping people in mid-market companies as well. And ultimately the commonality we have across all of our customers, across all these countries in the world, it’s these teams that are doing remarkable things that are doing more than they could have done before. And so this idea of small teams building a big business that just resonates. And at a time like today, most every marketing team, every marketer I talk to, they’re being asked to do a little bit more with less. And there’s this sufficiency. There’s also this, there’s a lot of businesses trying to figure out how do we grow in this new situation that we’re in? And you put all that together and it just creates this opportunity to help unlock growth, help be that partner, that additional team member in a way to the marketer, to that marketing team.

John (13:32): I think that’s some of the initial allure or promise, whether it’s true or not, we can debate of ai. And what role does AI play in your roadmap as a part of the tool, as a leading edge of the tool? How do you see it?

Jason (13:50): Yeah, so I think a lot of people have been focused on AI in the way of content, and I think that to be helpful, it’s like a helpful tool for the marketer, but I think that’s a small piece of it that in reality what we’ve already been trying to do is how do we take these ideas marketers have build upon them to give them the next kind of light bulb moment. So when I think of our product roadmap of where we’re investing from the AI standpoint, there’s some of that in terms of content, getting content very personalized down to the individual contact, but kind starting with the root of what the marketer thinks it should be, and then focusing even more time on what is that next part of the journey the marketers should be thinking about, what’s the next part of the journey the marketers should be crafting? How can we start to preset some of that for them? So then give them these light bulb moments that’s already kind of like in a structural format with content, everything like that. But then they can take their own, they know the business better, they know their customer better and craft from there. I think that assist type of mode is where I have the most excitement.

John (14:52): I mean, is it an oversimplification to say it’s just better lead scoring?

Jason (14:57): I think so because I think lead scoring by itself is just thinking about typically trying to group people into segments or buckets and rally the different types of paths one can create at a customer experience, the different ideas of what are you not already doing? Maybe it’s something you’re not doing for repeat customers or maybe you’re just missing nurturing in different parts of the life cycle. Figuring out based off of where others have had success and where things could make sense to explore ideas like that that you are not thinking about. But to your point, I think part of it also is here’s a bucket of contacts and that just should be marketed a different way, should be having a different customer experience. But I think it can be far more of this. The best way I can describe it’s this light bulb generating machine with that also gives you some of the structure as well.

John (15:51): So 2024 has an extra day in it. February 29th leap day in leap year, you guys are doing a kind of fun event, an audacious event. Maybe I’d let you describe it, but a little about your leap day.

Jason (16:07): Yeah, so we see it as leap day provides extra time, it provides an extra ability for people to get more done through the use of automation. That’s also building on this idea of save time, let’s be able to do more with it. And that allows you to do other things in your business, other things in your personal life, whatever it may be. And so yeah, we have this very subtle idea of doing a very long online event all focused around the marketer and how to build out more for your business customer experiences and through automation. And we have an exciting array of sponsors all lined up that have all gotten together that we’re all working together on, and tremendous amount of speakers as well, providing something that not only fits an entire day, which is pretty crazy for an event, but across all these different regions as well. And the exciting part about that, at least that I’m personally really excited about too is there’s different tactics, there’s different ways, there’s different themes, there’s different macro situations throughout the world that’ll come to life as part of this as well. It’s going to be pretty exciting.

John (17:13): So you didn’t say it as directly, but I mean you’re literally going to run for 24 hours. The event is going to go when people are sleeping in one part of the world and watching it in another part of the world.

Jason (17:26): And actually longer 29 hours we’re going to hit all the days around all the, a

John (17:33): Lot

Jason (17:33): Of, I think there’ll be a couple people that are around for the whole thing. The expectation is not everyone watching it live all the entire time, but it’s going to be quite an interesting event

John (17:44): And there ought to be some sort of award for that. If somebody can actually do it for 29 hours, you got to have some prize for that. That sounds amazing. Really, like I said, very innovative, very clever. Should get tons of attention. When we were talking, again, I think off air, this part of it, you’ve been the CEO of this company for 20 plus years and you mentioned, and I thought this was really exciting to hear that you still don’t get bored. I mean, you don’t get bored with what you’re doing on a day-to-day basis. I tell people that about my work as well. What’s an average day for a CEO of a, I’m going to get the number wrong, 750 plus person organization.

Jason (18:24): It’s very much around some of the themes that we’re working on. I take a particular interest in the product side of the business. Where are we going? How does that influence, how does that work with our customers, our partners? I won’t be talking to them all the time. And then how do we really get alignment just as a company? We’re spread out across the entire world. We’re in 170 plus countries in terms of customers, we have team around the entire world. How do we get this rallying point of how are we going to actually help make more time for all of our customers? How are we going to help give more of those light bulb moments for customer experiences and then just continue to scale all aspects of the business? So a good portion of my time also is just on team and building, aligning all sorts of things that it’s very different than a few years ago, but as I was describing, it’s just continual evolution of challenges and experiences and continuing to see that impact we’re having on so many brands.

(19:24): And that’s exciting about the event coming up for the Leap Day event as well. It’s just this, if we’re able to help anyone find, make more time and their day-to-day or to be able to do more with their business, automate more with their business, that can be truly changing for someone’s, just what they’re able to do within that role career at the business as a whole. And that’s something that they can only build on over time. It’s never done. I think that’s the both building a business, but then also this idea of marketing, customer experience. What can you automate the blend of automation, human touch, you’re never done. Every time you find a little more ability to craft it, that next thing is all of a sudden the new light bulb pops up. And that’s why we’re trying to play that role of here’s this next idea of to make more time for yourself and for your business.

John (20:14): Awesome. All right, one last question in a personal question. Anything on your bucket list outside of work next five, 10 years?

Jason (20:22): That’s a good question. Nothing that

John (20:23): You got young kids, right? You’re just trying to survive.

Jason (20:26): Honestly, it’s like where I’m at right now in life with young kids. My bucket list is what they want to do in life and making sure I can make enough time to both try what they’re trying to do. Whether that be something I can totally fail at and hurt myself with or not in terms of sports and activities, but really finding, and that’s why I love automation as well. It’s this idea of how you more time for those moments in life that matter the most.

John (20:54): Sounds like since you’ve moved to Colorado, you’ve taken up mountain biking. That’s what I’m guessing.

Jason (20:58): A little bit of biking. Yeah.

John (21:01): I myself have taken up mountain biking in the last five years and when you said try not to kill yourself, that’s kind of where I am at Mountain bugging. Yeah. Awesome, Jason. Well, it was great having you stop by the Duct Tape Marketing podcast. We will have a link to the Leap Day extravaganza in the show notes. Anywhere else you want to invite people to maybe connect with you and find out more about what you’re up to.

Jason (21:22): Yeah, no, definitely check that out. I’ll be around during most all of the events. I’ll try to make it 29 hours. We’ll see. Feel free to reach out directly through that online email, anything. But appreciate having me and really enjoyed the conversation.

John (21:37): Awesome. Well hopefully we’ll run into you out there on the ski slopes or something. In real life.

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