Navigating the Challenges of Scaling

0:07Hello and welcome to another episode of the Duct Tapeaket marketing podcast. This is John Jantz, and 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 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.

0:52He's a self-taught software engineer and technologist. So, Jason, welcome back to the show. Yeah, thanks for having me. Looking forward to chatting. So, this is at least your third time on the show. And I think we were laughing about it off air that, you know, the company was just a couple of years old. And 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, you know, 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 enterprises. Is there any reason that you said, no, we're going to go that.

1:30We're going to go after that segment and focus on it. Yeah, I think there's a couple of things. One, just a big believer in this idea of like, over delivering on value, right? 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 a it's that individual marketer, small team of marketers looking to do more. It's almost being that additional like team member within that company. one of the one of the most impactful things that I've found at least like building a business is just the impact like 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 you're 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 looking at that as hard to serve larger companies.

2:26That's fine for them, but there's a real need opportunity and it's a challenge, which is exciting. Yeah. So, you know, 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. You know, that kind of scrappy mentality, have you been able to keep that in the culture and the values? 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.

3:06And so I think the key for me is like, 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 gonna get farther and farther away myself, right? How to replicate that across, you know, 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, right? And you can take these stories, you can bring customers to meet the team. Like it's like the purpose behind what you do is something I think people don't always focus enough on.

3:44And that purpose can be very motivating. It It can be kind of a rallying cry. It can help drive what you're looking to do as a business itself. Personally, how has your life changed? You started, you didn't have kids when you started this company. You're now the CEO of a, you know, really a leader in a very large industry. What's it done to, I don't know, work-life balance? I hate that term, but what's that done to like, how have you maintained sanity? Let's put it that way. Yeah, I think like it's changed, right? And I think the only, like just the, just constant change. I think that's what makes it exciting.

4:19Like 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 of a boring operating model in my mind, right? And so I think it's just, it's building team, but it's building team and I'm close to that customer experience, close to the customer and ultimately having to focus on different things over time, but like it's the, 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. Like that's where I put a lot of my time and energy, which is very different than like earlier on where it would be like actually writing code or doing something like very.

5:02So a lot of times when people look at companies that have really been very successful, or at certainly outwardly appear that to them. We don't have all the like behind the scenes, you know, are there any kind of personal or business like failures where you went, well, hopefully we learned something from that, but that was a disaster, right? Anything along the way that I think it's actually helpful for people to hear that when they're growing a business. No, I think there's like a, like it's just a countless running list of maybe not, I want to call them all disasters, but of these learning moments.

5:37But I think it's, to your point, like, 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 an entire company, try to surface, obviously, like the wins and like the positives and stuff like that. But also like try to surface and celebrate, like we tried this thing, we all rally behind it, total failure. Cool. we realize that success in itself and that's moving, that's really hard to like 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.

6:14And so failure is not even thought of as like, we, you know, didn't do something right business wise, but it's like people take that on as like their personal connection. We spend so much time working. We spend so much time in this work atmosphere, right so it makes sense but i think it's this you have to like both as an individual but then try to get others to like identify a failure call it out in not a terrible way but just like if we can call it out quickly that success to just build this idea of iteration and that's something that's always been i've been obsessed with is like how do you just continually iterate and find these like little moments of progression when i think of failure moments that stand out it's like when we get too locked into an idea.

6:57Like 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 like, just we blinded to the reality of different data points, different things that are showing us maybe it's not the right move or like the customers and customers are not responding to 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.

7:30And that's when it becomes that's when it moves from failure is like kind of a good thing. Realize it to like you just wasted a bunch of time. A lot of startup founders have to actually learn to be managers. Sometimes never managed people and certainly never managed managers of people. I mean, is there any kind of like one people management philosophy that you swear by? 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 reality.

8:10what I found is like, it's quite the opposite, both when it comes from founder to founder, but then also like different functional roles. Like there is a people that have gone through different experiences of learning, you know, going from not managing anyone to manager or 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 like an annual cycle or something like that.

8:53I've had a fellow Chicagoan on the show, Jason Freed, founder of Basecamp. And, you know, one of their philosophies was, you know, you don't build features in just because people ask for them. But I'm sure you feel pressure all the time, right? People are wanting just make it do this little thing or do that little thing. How do you make decisions about how to innovate? It has to be guided. Like, so customer feedback is so important. Partner feedback is so important. it helps guide the like themes of where you should focus. But if you do it exactly how someone is describing it, it's probably been done before.

9:31You're going to lack innovation by the very fact of like, it's trying to replicate something. Right. So to try to get to that root cause of like, what is actually trying to be solved? How can we do it a little bit differently? And then also to your point, like, 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 have been a million dollar plus type of contract type of deal. It was just like, we're just going to take a quarter or two of our roadmap, right? So like get certain things.

10:03And it was this real testing moment of like the team was like, 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 like 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. And that situation, we actually chose to not pursue and not go forward with that opportunity.

10:41probably looking back at it the right call in the moment painful sad kind of happy we made the right call so it's my pleasure to welcome a new sponsor to the podcast our friends at active campaign active campaign helps small teams power big businesses with the must-have platform for intelligent marketing automation we've been using active campaign for years here at duct tape marketing to power our subscription forms, email newsletters, and sales funnel drip campaigns. ActiveCampaign is that rare platform that's affordable, easy to use, and capable of handling even the most complex marketing automation needs.

11:23And they make it easy to switch. They provide every new customer with one-on-one personal training and free migrations from your current marketing automation or email marketing provider. You can try ActiveCampaign for free for 14 days, and there's no credit card required. Just visit activecampaign.com slash duct tape. That's right. Duct Tape Marketing Podcast listeners who sign up via that link will also receive 15 % off an annual plan if purchased by March 31st, 2024. That's activecampaign.com slash duct tape. Now this offer is limited to new Active Campaign customers only. So what are you waiting for?

12:03Fuel your growth, boost revenue, and save precious time by upgrading to ActiveCampaign today. 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? So we've always been about like, how do you unlock more? How do you allow that individual or that team of marketers to punch up, 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.

12:40Right. And so we've always been trying to describe ourselves of like, we're SMB friendly. Like 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 like, there's a sufficient, there's also this like, there's a lot of businesses trying to figure out how do we grow in this new like situation that we're in.

13:20And 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. No, I think that's some of the initial allure or promise, whether it's true or not, we can debate of AI. And, you know, what role does AI play in your roadmap as a part of the tool, as, you know, a leading edge of the tool? You know, how do you see it? Yeah. So I think a lot of people have been focused on AI in the way of content. And I think that can be helpful. It's like a helpful tool for the marketer, but I think that's, that's a small piece of it.

14:00In 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 like 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 of starting with the root of what the marketer thinks it should be. And then focusing even more time on like, what is that next part of the journey? The marketer should be thinking about what's the next part of the journey. The marketer should be crafting.

14:32How can we start to preset some of that for them? Then give them these light bulb moments. That's already kind of like in a structural format with content and everything like that, but then they can take their own. They know the business better. They know like their customer better and craft from there. I think that like assist type of mode is where I have the most excitement. I mean, is it an oversimplification to say it's just better lead scoring? I think so, because I think lead scoring by itself is just thinking about typically like trying to group people into segments or buckets. And really the different types of paths one can create at a customer experience, the different ideas of like, what are you not already doing?

15:16maybe it's something you're not doing for repeat customers or maybe you're just like missing nurturing in different parts of the life cycle figuring out based off of where others have had success and like where things like could make sense to explore ideas like that that you are not thinking about but to your point like i think part of it also is like here's a bucket of contacts and like that just like should be marketed a different way i should be having a different customer experience but i think it can be far more of this the best way i can describe it is this like light bulb generating machine with that also gives you some of the structure as well.

15:51So 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 tell us a little about your leap day. Yeah. So we see it as like leap day provides extra time, right? It provides an extra ability for people to get more done through the use of automation. That's also building on this idea of like, 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.

16:39And 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 kind of fits like an entire day which is pretty crazy for an event but across all these different regions as well and then the exciting part about that at least that i'm personally really excited about too is like there's 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. Yeah. It's going to be pretty exciting.

17:12Yeah. So you didn't say this directly, but I mean, you're literally going to run for 24 hours, right? The whole event is going to go, you know, when people are sleeping in one part of the world and watching it in another part of the world, right? And actually longer, 29 hours, because we're going to hit all the weekdays. around all the, yeah. So it's a lot 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 a, it's going to be quite an interesting event. And there ought to be some sort of award for that.

17:46If somebody can actually do it for 29 hours, you know, you ought to have some prize for that. That sounds amazing. Really, like I said, very innovative, very clever, should get tons of attention. You, you, when we were talking again, I think off air, this part of it, you know, 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?

18:24It'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 want to 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 like 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 like on team and building aligning like all sorts of things that it's very different than a few years ago but yeah as i was describing it's like it's just continual evolution of challenges and experiences and continuing to see that impact we're having on so many brands.

19:24And that's what's exciting about the event coming up for the LeapJ event as well. It's just like this, if we're able to help anyone find more time in 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 like what they're able to do within the role, career, at the business as a whole. And that's something that they can only build on over time. Like it's never done. I think that's the, like both building a business, but then also this idea of like marketing, customer experience, what can you automate? The blend of automation, human touch.

19:58You're never done. Every time you find a little more ability to craft it, that next thing is like, all of a sudden the new light bulb pops up, right? And that's why we're trying to play that role of, here's this next idea to make more time for yourself and for your business. Awesome. All right. One last question and a personal question. Anything on your bucket list outside of work next five, 10 years? Oh, that's a good question. Nothing that you got young kids, right? You're just trying to survive. Honestly, it's like where I'm at right now with young kids. It's 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 it.

20:46And that's why I love automation as well. It's this idea of more time for those moments in life that matter the most. Sounds like since you've moved to Colorado, you've taken up mountain biking. That's what I'm guessing. A little bit of biking. Yeah. I myself have taken up mountain biking in the last five years. And when you said, you know, try not to kill yourself, that's kind of where I am at mountain biking. Awesome, Jason. Well, it was great having you stop by the Ductate 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?

21:22Yeah, 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. Awesome. Hopefully we'll run into you out there on the ski slopes or something in real life.