Category Archives: Jason Vandeboom

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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. 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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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.

Transcript of The Ins and Outs of Marketing Automation

Transcript of The Ins and Outs of Marketing Automation written by John Jantsch read more at Duct Tape Marketing

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John Jantsch: This episode of the Duct Tape Marketing podcast is brought to you by Gusto, modern, easy payroll benefits for small businesses across the country, and because you’re a listener, you get three months free when you run your first payroll. Find out at

John Jantsch: Hello and welcome to another episode of the Duct Tape Marketing podcast. This is John Jantsch and my guest today is Jason Vandeboom. He is the CEO and founder of the CRM and marketing automation platform known as ActiveCampaign and we’re going to talk about how CRM and how relationship building and how email marketing and marketing automation have changed for the better. Jason’s going to talk about some of the things they are doing there at ActiveCampaign. So Jason, thanks for joining me.

Jason Vandeboom: Yeah, thanks for having me. Looking forward to it.

John Jantsch: So you know, marketing automation has been with us for a while and it certainly was a real boon I think for a lot of folks that were at least attempting to kind of help drive the funnel or drive people down the funnel or whatever the term that they used for it, but it’s really not that personal or at least in the traditional way. I think a lot of people have found a lot of ways to abuse it, let’s put it that way. So what is your take on marketing automation space in general right now?

Jason Vandeboom: Yeah, I think if you look in the past, it started from a good place, saving time, maybe personalizing experiences and whatnot, but ultimately the focus has been so much on kind of the time savings, replacing humans as much as possible and that leads to experiences that are less than ideal. Also, as an industry, we always talk about personalization, we talk about highly personalized to the contact level, but then when we look at what you can build within marketing automation platforms, it’s oftentimes personalization doesn’t mean personalization by the individual. It means a grouping of people or a segment of people getting these unique experiences. So that makes them not actually that unique at all because there’s so many other contacts or customers going through that same workflow.

John Jantsch: Well, and I think there’s no question that at least… You know, you go to the conferences today and everybody’s talking about personalization, personalization, and I think that for some people it’s not gone beyond, Hey, first name, here’s my email.

Jason Vandeboom: Exactly. Yeah.

John Jantsch: And I think that that’s the nut we have to crack, isn’t it? I mean, it’s great talking about personalization, but how do we do it? I started the show off talking about customer experience automation and predictive sending. So let’s just lay that out. I mean, how does that work that’s any different than designing campaigns so to speak?

Jason Vandeboom: Sure. Yeah. And I think there’s those two focuses, it’s the bringing humans in at the right time and then functionality that can be developed and predictive sending is a good example of that where instead of thinking about messaging that’s delivered at the same time for a group of individuals, really learning from the contact level when is the best time, and not just when is the best time to open, but when is the best time for someone to be willing or open to respond to the engagement from the brand.

John Jantsch: Let me stop you right there because I just want to clarify that. So how would… Let’s say we send out, we have this list, we think they all care about the same thing or they care about the same product and we send them an email or something that explains a new offering. I mean, how would then timing be changed? Would it be changed based on the behavior, how they interacted or didn’t interact or what they did would, would actually automatically sort of put them in another timing?

Jason Vandeboom: Yeah, so a couple of different things. If you don’t know a lot about them, then we have to go to baseline ideas that have been done in the past of just like overall time zone, overall characteristics, compared to other contacts that kind of follow the same attributes and whatnot. But then as you get a better understanding of that individual, the timing should change. So predictive sending is very much about a message going out, right? But where we’re going with that as well is not just like in terms of a message, but think about predictively figuring out the optimal time for a sales rep to reach out. So really finding that blend of like automation and human touch, because timing plays such a key role with most any sales process and also post-sale process of getting someone to actually see value out of whatever you’re selling.

John Jantsch: So another thing that’s very common is we’ll have an ebook. It has a great promise, a great message, and people want to get it, but just because they downloaded that, I mean doesn’t necessarily mean… I mean they were solving a different problem. They were in a different stage of their journey or searching. I mean how do we then kind of take this thinking and say, “Okay, let’s add what we think they need in terms of content”? I mean how do we actually, so not just send different timing but maybe different content altogether? Is that part of kind of the new norm?

Jason Vandeboom: Yeah. No, I think that’s something that has been talked about for years and years and years and it’s ultimately fallen into the idea of just like then use split testing or something like that. Split tests down emails is nothing new. Split testing within an automation workflow is something we’ve had for quite some time and some others have started to grow their own versions of that, but ultimately that still is trying to figure out like one solution that’s going to work well for everyone or for a group or for a segment of contacts, when in reality what we should be thinking about is within that content of the message, whether it be an email, whether it be on another channel, determining based on that individual contact what type of content would work best and not necessarily trying to find the number one winner across a variety of options.

Jason Vandeboom: So doing that for messaging is very much… that’s kind of where we’re spending a bunch of time right now and then also taking the concepts and fundamentals of like split testing actual workflows, but doing that in a way where it’s not split testing to some singular end result, but actually finding the right paths and the right content by the individual contact.

John Jantsch: And so the implication, if we’re going to use the word automation here, is that I’m not just sitting here with a giant spreadsheet of all my split tests and plugging in data and then redirecting or remessaging. The idea here is that there’s an automation aspect of that.

Jason Vandeboom: Exactly, yeah, and that there’s an intelligence built in where to try to create those, like right now it’s very static experiences that you have to try to create to create these personalized workflows. Instead of having to build out thousands, tens of thousands, of workflows to try to get that granularity and personalization, that trust can be enabled within a platform to help you get there faster.

John Jantsch: For those that aren’t familiar with the backend or workings of ActiveCampaign, they use something they call automations where you can kind of drag and drop, do this, then do that, if they do this do that. So how, with that really, really brief explanation, how has now… how has the artificial intelligence that’s being built in here and the decision making process, how does that change that kind of drag and drop approach?

Jason Vandeboom: Yeah, so the approach is still there. It just provides… That’s the general theme of a direction. Meaning a good way of thinking about automations is just thinking about a flow chart. You have a start with your flowchart, that’s typically the trigger. Something happens to create the automation and then you have a sequence of events like you said, and then the only time you have actually different experiences would be if you have like if and else, so like if an action occurs then do something, otherwise go down a different path. And that’s how you create that like tree looking situation within a flowchart.

Jason Vandeboom: So taking that but making the actual paths vary by the contact and the independent timing between those actions, whether it be sending a message or when’s the optimal time to get sales or customer success involved, and then also within the content. So you’re personalizing the paths, you’re personalizing the actual content, you’re personalizing the timing, creating a really going from a static experience that everyone sort of hits all those check boxes at the same time with the same content to something that is far more dynamic and individual to the individual contact.

John Jantsch: And so then is the software platform merely making recommendations to me as the user that hey, we’re seeing this or this format of content is getting all the play. You ought to move this direction or is it just automatically making those alterations for me?

Jason Vandeboom: Yeah, so we believe that nobody would really trust it out of the box if it was just like we’re going to make all the decisions for you. So instead of that, you still know your business more than anyone else at the end of the day. So you probably know your customer propel, you know what will probably work one way or the other. So allowing you to kind of set that up and then choose as you gain more and more confidence with the platform what you want to allow the platform to play around with, so whether it be the timing aspect or if you want to… you like the idea of personalized content, you don’t necessarily want to split test it and you want it to actually be a little bit more dynamic by the contact, allowing you to sort of enable these different pieces as you gain more and more trust.

Jason Vandeboom: Now we’re also working on ways where we can make suggestions. Things that maybe are not thought of today or maybe you have automations that are currently running and we’re seeing something with the data that just, you know, maybe you haven’t analyzed quite yet or just something that may not make sense outside of what the data actually tells and to surface some of those as recommendations, but still then allowing that business owner or that marketer to choose to opt in on some of those things. Eventually the idea is it should not… like a true platform that’s focused on CX automation shouldn’t feel like a tool. It should feel more like a business partner, it should feel like it’s actually adding value, enabling you to do more.

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John Jantsch: So one of the things that I think a lot of business owners struggle with obviously is you hear about a platform like this and you think, “Oh this is great. This is going to do all the work for me.” But in reality, if we don’t set our businesses or our lead capture processes up on the front end right, I mean it’s probably not going to collect anything that you could do anything with. So what are some best practices for say, routing and segmenting and capturing somebody… enough data about somebody so that we can kind of understand what bucket to put them in even?

Jason Vandeboom: Yeah. So a couple things. I would say one err on capturing more data than you may even think you need right now. By having that capture and having that capture historically allows you to actually be able to do something in the future. The other thing I would spend a lot of time, not so much thinking about tactically how you’re going to cause a conversion or how you’re going to cause certain actions to take place, but what are those key pieces? What are those key conversions that you care about?

Jason Vandeboom: Sometimes it’s obvious, like it’s actually purchasing the product or whatnot, but then with your own insight and knowledge into, going back to you know your business more than anyone else or any other platform from a different vantage point, what are those influencers you think that may assist along the way? Like what are those key points where someone starts to find value and whatnot? And that isn’t always like a quantitative sort of thinking. Oftentimes it’s much more qualitative in the way of you just think something has some sort of a weight to it. Where all the sudden they start seeing the value or they become a little bit more hooked with the product or service you’re offering.

Jason Vandeboom: When you start figuring out what those are, then you can build out more tactical execution as to how do you drive more of that behavior and how do you drive ultimately to that conversion. But if you’re not thinking about those and if you’re not thinking about the key conversion events, you’re really just going to struggle quite a bit and there’s nothing that can really help, because everything has to work to some end goal.

John Jantsch: Yeah, and I think one of the things that I’ve always struggled with frankly is I have a couple of very unique segments and some listeners are probably going to say, “Yeah, you’re not doing this well,” but they need very different messages, but it’s not always obvious who they are. I know that sounds really vague, but how hard is it in that kind of initial, hey, here’s a piece of content that you found really compelling. You wanted to give me your email address, but now I want to know who you are. And you know, common wisdom is, hey, just get the email address and don’t put any more friction up, but by taking that path, I’m also not learning how to serve them.

Jason Vandeboom: Yep.

John Jantsch: So help me out. What’s the best practice for should… Once somebody gives that and they get the content, should we immediately go to asking them to sort of self identify?

Jason Vandeboom: I think it’s a couple of things. One, I do believe in the less is more up front to get the process going. So maybe you just start with that email address. Based on that, ideally your first couple of pieces of content or first messages going out have some clear… like if it’s actual content that’s enabling something, there’s a couple of different varieties in there. So based on engagement with that, you can classify and don’t just treat it as like there’s a link click or something like that and now you know that someone has something. You can set maybe a tag or something to that contact so you have a general understanding, but then trying to find different ways, just basic like profiling of as they take more action over time to get something, either from their action or them to fill something out additionally in the future.

Jason Vandeboom: But it also goes back to just kind of testing overall, because there’s the what content are they interested in, which I think a lot of people focus on, and there’s the how do they actually like to consume the content, which I think more people need to focus on sooner than later. And that could be simple as like some people like to consume heavy content and versus like more of a CliffsNotes style and a bunch of different similar types of variations. But I think that piece focusing on both at the same time in small iterations, not trying to get it all at once, is probably the best path forward.

John Jantsch: So let’s outline just kind of a very typical use case. It’s really common these days to have an indoctrination series. So somebody is new to you, they come and they say, “Hey, I like what you’re doing here. I want to get this checklist. Get on your list, start getting stuff from you,” and then we kind of drip out, typically been written as an automation. Maybe we put two days or three days between each and we drip out what we think will be useful information in a sequence of maybe over 45 or 60 days. They should know, assuming they read it all, a lot more about us. How would that very common practice be changed in a CX automation predictive sending way?

Jason Vandeboom: Sure. So for one, instead of having a single piece of content each step of the way, ultimately having the ability to have multiple versions but not testing for a single source of truth. So as you have a better understanding of both what types of content they’re looking to consume but how they want to consume it, it can start personalizing to that behavior. Additionally, there’s different types of people for consuming the content and maybe different levels of maturity if you will or want for consumption in terms of timing.

Jason Vandeboom: So based on interaction, based on if we can start grouping things up based on attributes that are known prior, even if they’re anonymous attributes such as like the pages they visited, sources, things like that to possibly accelerate that entire process that you’re talking about, but to do both of those things at more of an individual level instead of just trying to get like the one overall, and I think that’s the theme of where things are going in the future is all too often in the past we’ve really tried to optimize for this one overall workflow or this one overall like drip set of emails that overall is the best. But we’re leaving a lot on the table by really having to just focus on the overall instead of thinking about it at a far more personalized level.

John Jantsch: So the typical sort of person that actually is very engaged, ready to solve their problem, they want to consume the content in five days instead of five weeks would get that experience because they demonstrated that behavior.

Jason Vandeboom: Yes. But then ultimately, you know, at the end of the day, try and get all of this to tie to like going back to those key pieces that you know that are going to be drivers for your conversions and your actual conversions as well, because at the end of the day that’s what we should all be optimizing for is those known sort of events or transformative moments where they’re actually converting.

John Jantsch: Yeah. So it’s just a matter of of how we deliver them to that event.

Jason Vandeboom: Exactly.

John Jantsch: Great. So what’s in the future then? I know we’re talking about stuff that is new and people are still wrapping their heads around, but I’m guessing that you’ve road mapped an evolution of this even.

Jason Vandeboom: Yeah, so quite a bit, and it all revolves… there’s a lot more to do with timing. When you start thinking about when humans are involved in any form of a process, the timing is so critical, whether it be a phone call or reach outs and whatnot. So really digging into that further. The content piece, we’re just sort of scratching the surface of. We’re investing quite a bit into that right now. Making a truly personalized content where we’re not just testing to a single end result, but really the best variation and trying to get predictive content across channels as well and not just stick to just email.

Jason Vandeboom: And then there’s the concept of like dynamic routing, so like we have, you know, as marketers, we create these funnels and whatnot that you’ve been describing and they’re not like normally just thought up of from nothing. They’re, to your point, it’s well thought out, been doing these for quite a while, and so allowing a marketer to create a couple of these and then dynamically placing context down them, but not necessarily testing for the single one answer, but finding the optimal one.

Jason Vandeboom: After that, it’s very much about how do we take all of these practices and provide predictions and provide ideas. So seeing all the data, so you know, all the movement doing these personalizations and whatnot, we should be able to predict more and more. So even as you start off as a marketer using the platform, you should be able to get guidance as to like, here’s something, here’s a recipe for a sequence of events that we think would improve sales by X or save Y number of hours building off how do you make more and more of these predictions and how you actually follow up with the outcome, that’s ultimately where we’re looking to go.

John Jantsch: Of course it means you have to pay attention to what’s actually going on behind the scenes doesn’t it?

Jason Vandeboom: Yeah.

John Jantsch: And I mean that sort of facetiously, but sort of not. Because it’s not a matter of setting these things up if you’re not going to analyze them and learn from them, then you know you probably won’t get nearly as much out of them.

Jason Vandeboom: Yeah.

John Jantsch: So Jason, I know people can find all they want about ActiveCampaign at but are you… this is June of 2019 so dependent upon when people are listening to this, are you doing conferences or any kind of roadshow or anything that people need to know about?

Jason Vandeboom: Yeah, sure. I’m at a couple of things in the upcoming months. I think Traction is the next conference I’ll be at. Otherwise we have, we’re doing over 200 marketing events this year throughout the world where we’re really talking about marketing strategy and whatnot and helping people grow their business. That can be found at, .com/events and then other than that, anyone wanting to reach out, I can always be reached at

John Jantsch: Awesome. Thanks Jason, and hopefully we’ll run into you next time I’m up in the Chicago area.

Jason Vandeboom: Sounds good. Thank you.

The Ins and Outs of Marketing Automation

The Ins and Outs of Marketing Automation written by John Jantsch read more at Duct Tape Marketing

Marketing Podcast with Jason Vandeboom
Podcast Transcript

Jason Vandeboom headshotToday on the Duct Tape Marketing Podcast, I visit with founder and CEO of ActiveCampaign, Jason Vandeboom.

ActiveCampaign is an SaaS solution built in the cloud that is focused on marketing automation. Managing everything from email campaigns to SMS messaging to sales and CRM is possible through the platform, and their predictive technology can help you to send highly individualized content to the right customers at the right time to generate the best results.

Vandeboom and I talk all things marketing automation and personalization on this episode.

Questions I ask Jason Vandeboom:

  • How do we really ensure personalization?
  • How do we manage customized timing and content within automation?
  • What’s the best practice for getting more information about customers after they’ve initially reached out?

What you’ll learn if you give a listen:

  • How to strike the right balance between automation and human touch.
  • Why it’s important to think about content delivery method as well as the message.
  • Why the future of marketing automation is about individualization.

Key takeaways from the episode and more about Jason Vandeboom:

Like this show? Click on over and give us a review on iTunes, please!

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Gusto is making payroll, benefits, and HR easy for modern small businesses. You no longer have to be a big company to get great technology, great benefits, and great service to take care of your team.

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