Jason VandeBoom: Inflection Points on a Journey from Side Hustle to 1000 People

Jason went against a lot of traditional advice for startups: staying in your lane; not going after big companies as your first customers; treating customer support as a cost center. Those unorthodox decisions have been key to the growth of ActiveCampaign.

Podcast

Transcript

Jason:

My background wise like, I just was very interested in building things at a young age, started with actually trying to build things physically and then I was fortunate enough to get a computer around 12 or 13, self taught kind of how to do to just like create websites, program, things like that. In high school wasn’t a huge fan of formal education, but was growing up in a small town talked them into letting me out half days for a work study program where I got to work at dial up internet company.

Basically just walked in with consulting work on a CD ROM said please give me a job, like please don’t pay me anything just like let me work here so I can get out of school and really allowed me to work with more and more businesses and I’ve just been kind of obsessed with this idea of like how do you create something of value to help people save time and help especially small businesses it’s a passion of mine. How do you help them grow.

Mark:

Right, so a little bit about active campaign that it was started off as a way of you funding your way through college. 

I suppose it just got a little bit out of control.

Jason:

Yeah, and so I started, they really wanted to focus on something continued to craft something because I was doing consulting work prior, I just moved to Chicago to go to fine art school. I’ve always had kind of a passion for the arts as well. And so I really just decided to create something that was a software company. Now I didn’t think about it in the way of like, I’ve got this ultimate plan on taking, taking on some market or anything I was just trying to get initially at the beginning $35 at a time. 

So when I first launched active campaign it was really just on a directory, at the time because it’s all the way back in like 2003, and someone bought a copy of it. I was able to, like, just receive the money and then I had to figure out like how to actually deliver it, and so I feel like I’ve been on this journey of just trying to figure things out ever since. Through so many different transformations and being fortunate to build grow the team and whatnot, but always just like always learning, and so like that’s been, that’s been an exciting part, and luckily like being at Fine Art School allowed me to have that flexibility of focusing on the business while going to school.

Mark:

So, you’re learning and you’re making it up as you go along. Would love to just test our zoom here and put your hand up if you’ve been making things up as you go along by using level reactions.

You can wave. If you’re making it up as you go along, 

Kirk’s not making it up as he goes along!

Nothing like a cheap, cheap shot for complete agreement. 

Jason:

I think it’s a good thing for people to, like, all too often I think people feel like they have to have it like figure it out, or even worse, there’s a right way of doing things. And the one thing I’ve learned is every time I like look at market, look at peers. It just like either takes me off course or just makes me feel bad about like what we are or are not doing, right, and then that that takes fun away from the journey, and given it’s like such a interesting journey of ups and downs of of either running or being part of a growing company. That’d be a real shame; they get rid of any of the any of the toy. Right. 

Mark:

Yeah. So, we’re gonna talk about kind of pivotal moments maybe and you obviously started this as a side project and it was a bootstrap thing for quite a while there, Most people would say there were probably two big pivotal moments between starting that thing as a project and getting to the size you are now and one is “I’m a company.” And then sort of later on because you bootstraps, pretty much. Certainly over over 10 years, then you have actually started to really grow and really accelerate and think you announced that big funding round last week. So yeah oldest dang that’s another, another big, big moment so tell us a little bit about that and how do you, how you kind of thought about that first bit from I’m just doing this thing. 

Jason:

Yeah, and I, I, so I look back at it and like I never thought of capital back then in the way of like I would be able to even get any. And I’m actually somewhat appreciative of that fact is it’s given us more optionality over time. But I think like, despite not raising capital, I had to find ways to like make it through difficult times. In like 2008, for instance, like we had no capital through that time. We’re working with small businesses and whatnot and the whole business sort of got into a critical state.

And just finding ways of leaning on some of our roots of like consulting, through different periods of time being fine with that. Also like finding ways of just like getting capital through other means, like, I remember when we got like an SBA loan, like nobody’s putting out like an amazing press release typically for that or like a cash advance on like your MRR line or something, but I feel like as a crew people should celebrate that stuff more because basically it’s what’s the difference, like there’s differences but like bringing capital into the business in a non diluted fashion.

Like, it’s actually it’s funny how like one side of it is so celebrated, where, why are we not celebrating like you know, credit card limits and things like it’s all like, you know the capitals returned at a certain point, right.

let’s let our customers lead our growth journey

So I think it’s the always thinking like, I didn’t really have a lot of ability to to find capital really created in the DNA of the company, just this, let’s let’s grow, but like, let’s let our customers lead our growth journey. So we’ve been fortunate to be able to get more momentum and whatnot but like, you know 13 years into the business, I went from like one to about 15 people.

And, you know, some people would look at that and say like, okay, it’s. So I think that was amazing business like we’re growing, we’re profitable, like it’s the problem is, if you look at competitors, if you look at market or something, those are not always the businesses being celebrated when they should be celebrated more. 

Because oftentimes, like in my opinion like half the time like half of those businesses are even more valuable than some of the ones, propped up right. And so it’s this, it’s kind of led to this place of where it may be, it sounds funny for me to talk about that now because we’ve, we’ve raised like $360 million. But it’s this no matter what we would raise I don’t think we could really remove some of those fundamentals from the DNA as a business, it’s just like in rooted in what we do where it’s, it’s just, we’ll move at the pace of our customers and kind of find the best of both worlds for what works for us at any given time

Mark:

So was there a point where you ever thought. It’s all too much bad just gonna give up, was there something in 2008, in that time or were there other other points?

Jason:

It’s just a lot of work right and it’s either, you know you have your different different areas where it becomes difficult it’s either, you know, customers or finding revenue. 2008 was the time where it just felt like, like, well, we make it through that, from a just a capital standpoint and just be able to pay people I stopped paying myself for over a year we just started tapping into everything we had and we had a team of eight people, and we just had to adapt but I’d say beyond that it’s, it’s just a journey of, you know, I think it’s normal to have feelings like that along the way.

Because it’s such a, up and down in terms of change and what I’ve really found is like the more you try to control the chaos of growth. You’re either going to highly frustrate yourself quite, quite, quite likely, but also the more control like like the more calm you try to bring the harder you can make it on yourself, because some of the some of the chaos is caused due to your customers it’s caused to do that like you’re gaining some momentum and whatnot. and every time I’ve tried to like stifle that maybe I’ll feel good for like a month or so but then all of a sudden it’s, it’s, it’s worse spot is similar in a way to, as you scale I think a lot of people try to remove the pieces that are maybe less, less fun.

Or maybe a little bit more painful and I know I’ve done that. So like we have a we have a lot of customers because we serve small businesses enough. And it’s hard to like look at all of the feedback or the churn reasons or something like that. It’s human nature to want to, you know, maybe have someone put together a report maybe glance at that once a month or something like that. But every time like I like, like, get a step away from from customer feedback or especially like, like why are people finding success or why are they leaving. I feel like I know my business last so like it’s API, more comfortable during the day because I’m just choosing to read happy things, but it makes me understand my business lessened probably grow less as an individual as well.

Mark:

Interesting. So, we will talk about what happens when you kind of go through that growth bet, and what you’re going to do with this new, new round of funding, but overall, I like this concept of optionality something that, in fact another Chicago based entrepreneur called Jason talks about – Basecamp – A lot. There’s a very big difference between doing something as a side project, and then even running this bootstrapped company, and then being responsible and running a company of 850 people now. Was it, was there ever a point when you thought, I’m not the right person. I’m not good enough or were there points where you felt you had to change and talk a little bit about today what what changes you’ve made, presumably it hasn’t been?

Jason:

So yeah, now it’s a good question and it’s interesting because if I think of like the time where you don’t call it more side project are starting, like there was still such a level of passion, and and work there, right. So I think that is something that remains more of a constant than not. I think sometimes people think of it as like, you start, you kind of like passive slow and then all of a sudden you like pick up speed. 

In reality, like being part of that business or starting the business I think it feels like you’re just moving at a fast rate, the whole time. Now, I’d say, like, every step of the journey has been like okay, like you see something far out, maybe it’s like team size, revenue, or whatnot and surely if I get there, like, I don’t know what I’m doing, like, how am I the right, you know person so I think there’s a lot of self doubt there.

It’s amplified because we look at the market, right, and that like what I was mentioned earlier it’s like human nature to look at like, oh so and so, like, is there they’re doing this I can’t even like deal with a team 1/10 of the size or something like that, like, how am I going to get there. And for good and bad like for the first 8-10 years of the business. I really didn’t go out and talk to a lot of people, meaning I didn’t go to events I just focused on building like I was, I was just focusing on just like programming working with our customers and whatnot. And I would probably tweak that a bit. But there’s, but by limiting yourself a little bit to like What is everyone else doing it almost like takes a little bit of that pressure off and allows you to either way like it’s probably more beneficial to go out there and talk to folks and whatnot. But like you need to trust your own instinct, a bit more. 

And so, countless times I’ve started to self doubt, like my own instinct on like how to how to build a company, how to work with our customers, things like that. And in those moments I look and see what are other people doing maybe I just follow that. And I think it’s that, if you’re, you know, if you’re starting to have even a couple customers if you’re starting to grow a team like there’s, there’s probably something like that you could give yourself a little bit more credit for along the way and it sounds so simple but like, even today, I’m having to constantly go back to that. And I think it brings a little bit more of a uniqueness and a little bit more freedom in the way of like how you’re thinking about operating And then that goes back to, hopefully it’s, it’s gonna be challenging. But hopefully, have some fun with that because if you start to lose that, then I think it goes into a pretty bad space. 

Mark:

So you do things differently and that’s something that you did I almost kind of attribute to some of that success, where do you get advice, if a lot of the advice that’s out there is the sort of Orthodox, this is what you do, this is what you do. Here’s the seven sexy secrets to SaaS success playbook, you know, blah blah blah. Where do you find those, where do you find those opinions those views?

Jason:

I’ve always been drawn to, like, if there’s a norm, like try to figure out like, Is there something you can do that’s, that’s a bit of maybe not a complete opposite but a play off of it or a bit of an opposite. For us, I mean like there’s there’s a ton of amazing businesses, helping us with these now but really staying entrepreneur and small business first has been a piece of that for us, instead of like we’ve had opportunities along the way to sort of just shift up market from a capital standpoint, from, like, people viewing or Ted like all your SaaS metrics like make some sense but like I think there is a greater opportunity going after something that’s more difficult.

I also just personally really enjoy finding things where it’s where it’s just questioned and challenged, meaning like, if we are not doing something that our customers aren’t like asking like why are you doing this, which seems counter to caring about your customers, it means we’re not pushing on innovation or having enough like some crazy ideas out there.

One good example of this was it would be before the pandemic, we started doing these study halls throughout the world and so we did hundreds of these events, call it like 25-50 people typically per event we’d be flying our team focusing on cities that were not your typical cities and going all over the world, and it was really focused less on like use Active Campaign buy Active Campaign, it’s more like, let’s look at your business. Think about your experience like how can you build it. Use Active Campaign if you want use something else otherwise. 

And so our customers actually liked it right like it was a, it was like free in person training like we like people were bonds and those groups and whatnot. Now my team was like, What are we doing, like, we’re spending all this money to send this team to a place to talk to 20 people in person, like this can’t be right, and one small example, but like it’s it’s doing things that cause those questions whether it be from your customers or from your team, that’ll always push the boundaries and maybe some of them are going to be, like, totally wrong. Right. Yeah, but in this case we’re able to actually look at the data and see just of the people at the event, due to their growth and retention, with the platform over time, it paid for it.

And then there was this rippling effect of advocacy in these like small regions that were not major cities, and you look at that and you think like that’s really expensive to do, but it’s, it’s actually cheaper than like pay per click or a lot of like the traditional marketing means of finding customers, and far more defensible, because if you can get someone into that like they truly like you they feel a bond with a business and whatnot. That’s like a type of growth, that, that your competitors won’t typically be able to buy because they have to go through all that effort to really build out programming and build that authentic advocacy overtime.

Mark:

So you know what this sounds like to me because I’m fairly kind of obsessive about bos and the bos speakers, but there’s a, there’s a talk from a while back that there’s there’s some echoes off of that. Gail Goodman. 

Jason:

Yeah, yeah, yeah, long slow SaaS ramp was a perfectly put.

But yeah, and there’s charges of early getting into communities at that like micro level and what not, truly powerful.

Mark:

Yeah, that’s interesting. So you’re growing up I mean you’ve grown as an individual, I’d love to talk about the things that you do now versus the things that you did maybe 10 years ago as a, as a co founder, but before that, the other kind of business but this is, you’ve grown, how did the team grow, and whether points were people in the team were growing as quickly as they needed to how did you how did you deal with that?

Jason:

Yeah, good question, I’d say like fortunate to still be working with a number of people I’ve been working with for like 10 years now on the team. So I think like, there’s been opportunities also like, I like to more celebrate folks that that choose to go do something else, but like, continue to do amazing things I think all too often we think about as like you know we’re on this journey, everyone has to be on this journey and it’s like well this is starting to sound like a cult so like maybe we don’t talk like that!

Maybe it’s about, you know, even if someone’s here just for a period of time and goes off and do something does something else like that level of impact and that type of reputation market is one that I think we should strive for.

Now early on. I tried to do a lot of that myself like up until I want to say 70-80 people.

I was, I was doing payroll and stuff like that really bad idea. Not good at it, fine art background. Next was programming, it’s gonna cause some problems, right. 

And so, I think it was this, I didn’t want to let go of certain pieces in regards to our own employee experience and what not, because I really wanted that to be like, I knew that’s going to be our throttle for growth right. If people are successful at Active Campaign but starting to build that out and since then obviously focusing more on like employee experience and building out different aspects of it, because it only increasingly gets more and more difficult.

And to your other point of like how things change, like, you know 10 years ago, I could go in and fix a problem, it could be more on people so it could be more on the technical it could be wherever.

Today, it feels like I can’t fix anything. Right, like it’s, it’s like a, you almost have to think a little bit further out and just try to like, steer things.

And it’s somewhat counterintuitive but that’s really the reason why you have to stay in the details though. 

So meaning like I didn’t take a lot of data from throughout the organisation. Probably more than, like some of my team is used to and other companies. And the point isn’t to necessarily go and solve something. I’m not the smartest person at Active Campaign by any any degree in any area.

It’s more like to just be another view into across things just asking the right questions to start to get, like, thought and proving something out right or wrong, sooner than later.

I think is really important, but it’s a different skill set I think I’ve had to build up over time and it’s a, it’s not easier I don’t think either, so like it’s. Now I got to still being all the details, but I can’t actually direct anything right like it’s, it’s, it’s great

Mark:

Sounds like becoming a product manager! So it’s just it wasn’t a point when you were growing that you lost people who’d been there for a long time? Was there a particular inflection point in that growth where people started to move on and what do you think caused that, and what lessons did you take from it?

Jason:

Yeah, no I think so and if I think about it like there were certain moments, probably around that like 50 or so people, certainly around 150 was probably the most, where it just felt like you know things are changing. I think it was a point in time, understanding that, you know, it’s one I have to message folks like it’s okay that things are things will change, we’re not going to stay the same company we’re, you know, it’s, we’re going to still focus on our primary focus believing we believe in but like culturally even that well, we’ll adjust over time.

And then also, like some people love to work in small businesses. Some people love to work and like, and kind of going back to at first like I, I think I approach that with the mindset of like we have to solve it like this is like really important to me we have to solve like how does this like be amazing for everyone!

let’s help people be successful.

And then I think that kind of like evolved into my view of let’s help people be successful. And so we’ve built out like different coaching options for folks internally, really bringing the idea of coaching and trying to extend that both from like from a, from a leadership standpoint, also from a mental health standpoint throughout the entire company and whatnot, and providing more and more resources along the way. 

And the thing is, like, understanding that all of this stuff we’re doing will potentially lead like a number of people away from active campaign and that’s fine too, like they’re gonna find some passion and like they want to go and, you know, do something totally different region totally different market like we should celebrate that. 

Mark:

Interesting, so we’re gonna talk about growth, and there’s some great questions kind of coming up in, not just the chat but various back channels here as well but you bootstrapped the business you were in charge of it, presumably you wrote and most of it may have been some kind of employee option program early on but you kind of got to the point where when you started to take money presumably that got you to a point where you weren’t a majority shareholder relatively quickly?

Jason:

I think there’s ways and I think we’re seeing more and more businesses like the longer they extend taking capital kind of point of optionality we’re talking about the more I don’t know if I always control, even the right word but the more control can be retained and I think it’s funny because like when I talk to people and they, they can’t raise for a long time, and then like, it’s like, oftentimes when you look back, it’s like well I’m sure glad like I was really bad at that like you know like it’s, it’s, but it’s one of those situations that maybe taking capital can actually give you some peace of mind to go forward too so it’s like, it’s an impossible, sort of sort of thing to say like, there is no right or wrong, right.

But I’d say it was 2016 late 2016 When we raised for the first time so 13 years into the business running on myself, no board, just like nice and simple, decisions can be made very happy when I was in that process, we had interest and whatnot but I did two different things that I think are important.

One: identic just paint like a super glossy picture I allowed room to show some areas that I knew might create some questions now that goes against all logical sense if you’re just purely going after valuation terms, things like that.

But I think there’s value you don’t have to like overdo it and only start negative and you probably won’t get any heavy any continued conversations, but like, being able to share some of that in a live or a video or even just an audio environment allows you to understand how do people think through it, how do they react. 

Two: I think the other point, that’s important that I always suggest people push on, is how do you bake in things that are for more beneficial to the company, or yourself as a founder or whatever it may be, than the investor.

Stuff that doesn’t even necessarily maybe isn’t even applicable for a while so maybe you bake in like super voting, like find different things and there’s like probably 20 different things you could kind of pick at that point there as well is, how does your potential investor react? Do they go like why are you asking about this, do they have trust in you or not. 

Now, this all comes from a place of like, if you’re in a spot where you don’t actually have to raise stuff like that. I think following those pieces and that’s something I’ve always just believed in doing is it really helps filter out some of the noise. At the end of the day like I don’t have any regrets about raising or the folks I’ve started to work, I can’t say it’s like for those reasons alone but like it’s helped out. 

Mark:

But you’re selling a different story at that stage that you were raising, because you were growing and profitable and been a pretty well established, you know you’re not selling a this is 100x Unicorn, but we know with a 9 in 10 chance of not returning anything you’ve got much more visibility., but there are things that you and it’s something that few people have raised. What did you look for in your investors that I beyond a load of cash? 

Jason:

Yeah, I think just the alignment and opportunity we’re going after first and foremost, which sounds obvious like you’d think anyone like human capital would but I think it’s, it can be like I didn’t want to have a situation afterwards where people are like, Why don’t you spend more to bring more customers on. It’s like no, we’ll just take the approach we’ve taken, like it’s also like for us being small business first there’s investors that like that and there’s investors that just don’t understand it. Right. And the ones that don’t understand it will just continue to, to push them up, or change the business. 

The other thing is like, like, not rocket science type of advice but like just finding like the failures.

So like with any capital we brought in, we’ve talked to companies and failures is a strong word perhaps but like companies that like is a failure in terms of the investors outlook, and talking to founder there. And also talking to the investor on the topic as well. And once again like catching that live video in person. You just start to gain a sense and at the end of the day there’s the, you know there’s there’s terms or stuff like that but you have to also be just be comfortable with people.

You’re not going to work with them every day, but like, Would you be okay with that if that was the case. That’ll never happen, but like, it speaks to the type of person that you’re going to have to deal with and operate with and like, I think that doing all of that hopefully puts you in a spot where you don’t actually manage to the board or manage your investors, where you can actually share with some transparency, feel like they’re not just going to like try to do whatever is in their interest versus like helping you along the way. So I feel like I’ve been very fortunate in finding like partners like that, especially with like our early funding and whatnot. 

So, but yeah it’s also like if you don’t have to rush it, don’t . 

So, but yeah it’s also like if you don’t have to rush it, don’t . Like it’s like kind of going back to what I was saying earlier, like if you can, if you can get a, like a MRR Cash Advance or something like that if you start to build up reoccurring revenue, Like I did that it’s basically like a, like a, it just gives you an advance of capital that you’d normally get and they just withhold some like, like I said it’s not going to be the most glamorous thing, you’re not going to get like big articles written up and whatnot but like, you’re going to get the capital, it’s not going to be diluted, like there’s there’s growing options in that area, which I think is really exciting for businesses looking for capital and so like I would look at it as, don’t raise for PR, don’t raise or any of that, like raise for the right reasons and try to find other ways to get capital, alongside or instead of

Mark:

So let’s talk about, you started taking this, you started taking capital and it’s pretty clear that you had a sense of, put some money in the center of the business, some more money comes up there, you’ve got this engine that’s engine that’s working and the capital is a route to making that happen. And that’s a different thing to building products and trying to go off and prove that prove the market, you started to grow pretty quickly at that point.

You had about a year of rapid growth and I think took some more funding and then something happened about this time last year, to the world can hardly remember – largely because I’ve tried to blot it out in my mind, what, what happened, how did you adapt?

Jason:

Yeah, No, it’s, uh, yeah we raised a couple months before the pandemic and obviously just a terrible situation for everyone in the world. And with focusing on small businesses.

I think we looked at it as like this is gonna be a time where we have to be there, more than ever before. The one thing like, so like if we ever enter like a difficult situation, whether it be 2008 the pandemic or just like we’re having a difficult situation internally, in terms of revenue growth, whatever it may be, like the only play I have is like doubling down on our own customer experience, it’s like the only thing that I can routinely go to feels like it works.

In this situation, we started looking at the data, like, every single day like analyzing by region, all that fun stuff. And then we went to our customer facing teams, as well as our product teams, and we basically said like okay, things we’re thinking about in the next 12 months, that we’re thinking about doing for our customers, maybe we’re like changing some of the services and stuff like that. Let’s get a list of all that. 

And then we started thinking Okay like of this list and there’s some pretty big changes, let’s do as much as we can in the next two weeks, and we just started doing that so on the customer facing side it was like actually changing a number of roles having teams focus in on different types of work, like, within days trying to communicate as much as possible through that. 

But I think people understood we were doing this to be there for our customers, more than ever before. And that wasn’t gonna be easy, but those same people were hearing like the stories transformations pains like businesses were going through so I think it was a time of a lot of change, all at once, but a moment where people really rally behind that, which I think is powerful and then on the product side really focused on I’ve always had this belief like building product that’s just like features, tools, probably useful to someone, but really doesn’t unlock the full capability. 

So how do we build it to be more of a partner to business versus just functionality, and in our world, it’s like recipes, giving people ideas of what to do, so that they don’t have to like map out things and just come up with ideas themselves, and a lot empowers business to get going without relying on consultants and whatnot. So we’re really trying to like help in that area like what can we do to really push that further, get more focused on transformation type of business processes and whatnot.

And just really focus on the customer, then that’s not necessarily an easy thing, but it’s always been something that during the moment I fully believe helps. And then, if you start to get outside of whatever that moment is like there’s no regret of doubling down on your own customer experience, especially through a difficult time, because then you gain even more advocacy, from those you’re able to help.

Mark:

Okay, so there’s a lot of questions:

Couple of things about the growth phase that you’ve been through that you talked about product you talked about getting closer to customers. You went from operating with how many kind of offices, but it was it was a pretty office based environment so a few offices around the world. Yeah, Chicago, Atlanta, Sydney Dublin. And then everybody was remote, but at least you had the luxury of not having to double your headcount, in a year. So what was the biggest, what was the biggest change for you, everybody being remote all of a sudden, or having to rethink the way that you approached, hiring and recruiting and onboarding?

Jason:

Yeah, I think the, I mean, it opens up opportunity to hire obviously from everywhere right, which more matches like Active Campaign in the way of like over half of our customers are international.

So, that makes sense I think coming from more of a hub/office driven model, we’ve always had all distributed as well. But, I mean we had some work to do, or used to be able to just talk in person and whatnot I think it also just showed like how, you know, Regardless how many people like how, how people will change transform and adapt pretty quickly.

And so, like, going forward, I think the real challenge is I had meaning, I don’t I don’t pretend to think I know what the future of work is I don’t think anyone really knows. I do think it’s centered around flexibility and that means something different for a lot of different people.

So like if I think of our team, you know, some people will want to be fully remote some will want to be hybrid some wanna be able to go to someplace so like it’s, we’ll still need to have these hubs for people to gather, if they want and when they want. But how do you maintain that, because I think where people have found a lot of success is going all in on a single model, which I don’t think is probably like if we’re able to get it to work across like a hybrid of approaches. That’s probably the right thing to do but we’re more in the just keep learning and trying things versus anything else.

Mark:

When you, when you decided on the first hubs that you were going to be opening up. What was, what was your thought process there were they, places that were existing to hire product or engineering talent or were they sales, marketing, operations, just wind back and talk us through that process of how that was gonna work and how it did. 

Jason:

Yeah, so look we’ve been fortunate that we have customers in 170 countries so we have like customers or some level of growth and just about any region we’re primarily focused on Chicago for the longest time, and we knew we’re gonna start with one new hub right. And I think the, the easy one would have been go to Dublin or something like that as the first one. 

Well, like in our typical fashion, it’s like, well, let’s just go to the one that like we have no timezone overlap at all. Start there. We’ll figure that one out and then, then we’ll go from there and we’ll see what happens. And so that’s why we started with Sydney, Australia and had had some some amazing people go over there and help start the office and whatnot. 

And then from there we kind of taken that approach elsewhere and so if I think about, you know we’re in all these countries, we got over 50% International without any intention, outside of localizing product. And I think that’s important to note because I think people think about it as this overly complex thing. All too often, where you have to have this full strategy people on the ground like in some businesses that’s, that’s maybe the case and a lot, you can get pretty far with very little intention. 

Now when we thought like okay let’s start actually localizing the sales and marketing site, like maybe that’ll be good let’s start offering in a local currency. We chose Brazil as our first place to really go all in on that, which also isn’t typical like it’d be making far more sense here somewhere within Europe or somewhere else.

But we also did that because we saw opportunity, and we knew there was going to be some challenges and all of that. But we saw by doing that, it makes other markets that we’ve now gone with more intention of a different flavor like easier as well as gives us a bit of edge in market as well because we’re chasing things that people are not necessarily all the time.

And I think that’s the, that’s kind of how we sort of guide a lot of decisions.

Mark:

Great question from our pajama watchers in Sydney, how did you cope with the timezone difference with your first overseas office being so far away so firstly I’m greatful that Tim recognizes that he is far away. And it’s not that we’re far away from him. Did it change your communication and meeting culture in head office?

Jason:

Yeah, I mean a lot of that before was in person so I think it was more going to like written and whatnot. We struggled a little bit with the timezone overlap though, because there was really no good overlap, and we really found a lot of team members, sort of working a lot of extra time to accommodate that versus us finding a way to do it. It started making us think about everyone was working almost a singular time even in Chicago so it really amplified the problem. So really getting more flexibility there.

And then I think that was the start from a lot of that of me really just trying to communicate and talk to the company, in a way that I don’t talk about it as like a Chicago headquartered company. I’m using more like we’re one global team, like we had a company update recently. And we changed the times of those all the times like this one was like at like eight o’clock in the morning or something, then we’ll do some more in the afternoon, something like, And it’s just like knowing that we’ll never have a time where it overlaps everything, but really caring about, you know, how do you talk in a way where it doesn’t feel like anyone, and this goes, whether it’s a hub or someone that’s distributed feels like they’re like a satellite, small, you know, operation off to the side and there’s like this thing going on somewhere else.

I don’t think we’re perfect there I think we’re still working on that. But I think that’s a that’s a fun challenge.

Jason VandeBoom

Jason VandeBoom is the CEO of ActiveCampaign, founded in 2003 as a means to fund his degree in fine arts. He’s a self-taught software engineer and technologist.

ActiveCampaign is a marketing automation platform designed for great customer experience. ActiveCampaign has over 145,000 customers in more than 170 countries and 850 employees with plans to hit 1,000 within the year. Jason went against a lot of traditional advice for startups: staying in your lane; not going after big companies as your first customers; treating customer support as a cost center…

Those unorthodox decisions have been key to the growth of ActiveCampaign.

More from Jason.

Next Events

BoS Europe 2025 🇬🇧

🗓️ 31 March – 1 April 2025
📍 Cambridge, UK

Grab early bird tickets until TODAY

Spend time with other smart people in a supportive community of SaaS & software entrepreneurs who want to build great products and companies.

Lock in Early Bird Pricing

BoS USA 2025 🇺🇸

🗓️ To be announced soon
📍 Raleigh, NC

Learn how great software companies are built at an extraordinary conference run since 2007 to help you build long term, profitable, sustainable businesses.

More Details