Welcome to Episode 207! Jason VandeBoom is the Founder and CEO of ActiveCampaign, a sales and marketing automation platform that enables small businesses around the world to meaningfully connect and engage with their customers. Jason founded the company in 2003 and under Jason’s leadership, ActiveCampaign has flourished from a successful but small company and then in 2013, they transitioned to SaaS. Since, they have grown to more than $50 million in ARR in less than five years, while still maintaining profitability and its culture. They have also only raised a single $20m PE round to accelerate their growth, making them a market leader in terms of funds raised/ARR generated.

In Today’s Episode We Discuss:

* How Jason made his way into the world of SaaS and came to found ActiveCampaign.

* Why is Jason so bullish that “SMB first, works?” What are the inherent benefits from starting at SMB? How does it affect product feedback? How does it affect how you build and scale your team? How does one start to layer in market and enterprise over time? Why does it give you additional leverage?

* What does Jason think is the right way to scale your sales team? Why does one not need funding to scale sales teams? When does Jason believe is the right time to hire your first VP of Sales? What were the biggest mistakes that Jason made in the scaling of his sales team? Why should you hire 3 reps to start at one time?

* How does Jason view the current fundraising environment? Why does Jason believe that “no one cares if you get funding?” Why does Jason believe there is a fear around needing fast growth? Who is to blame for this? How should founders in the messy middle feel when seeing large fundraises in the media?

* Why does Jason believe that all leaders need to be consuming all feedback? How does Jason consume feedback on a daily basis? What metrics and elements does he look for in this assessment? How has Jason’s role changed over the 16-year CEO-ship? Does it get easier over time in Jason’s mind? What has been the biggest challenge?

Jason’s 60 Second SaaStr:

* What does Jason know now that he wishes he had known at the beginning?

* No man’s land of SaaS pricing, exist or a myth?

* Multi-year deals, all they are cracked up to be or overrated?

You can also take your SaaStr to go:

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Listen on Spotify.

If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
Harry Stebbings
Jason VandeBoom


Harry Stebbings: Hello and welcome back to the official SaaStr podcast with me, Harry Stebbings. I would love to see you on Instagram, @HStebbings1996, with two Bs, where you can suggest both guests and questions for future episodes, and it would be fantastic to see you there.

But to our episode today. And I have to say, I’m really very proud of this one. Today we’re featuring an incredible entrepreneur in the form of Jason VandeBoom, founder and CEO at ActiveCampaign, a sales and marketing automation platform that enables small business around the world to meaningfully connect and engage with their customers.

Jason founded the company in 2003, and under his leadership, ActiveCampaign has flourished from a successful but small business. And then, in 2013, they transitioned to the world of SaaS. Since, they’ve grown to more than $50 million in ARR in less than five years, while still maintaining both profitability and its culture.

And they’ve also only raised a single $20 million private equity round to accelerate that growth, making them really, I guess, a market leader in terms of funds raised to ARR generated.

I do also have to say a huge thank you to Jason Lemkin for the intro to Jason, today, and so appreciate that. However, you’ve heard quite enough of my terrible English accent, and so I’m absolutely thrilled to welcome Jason VandeBoom, founder and CEO at ActiveCampaign.

Jason, it is absolutely fantastic to have you on the show. As I said, so excited for this one. So, thank you so much for joining me today, Jason.

Jason VandeBoom: Yeah, appreciate you having me.

Harry Stebbings: Not at all. But I’d love to kick off with a little on you. So tell me, how did you make your way into the world of SaaS, and come to found the beast that is today ActiveCampaign?

Jason VandeBoom: It’s actually kind of a long story in the making. If anyone’s not familiar with ActiveCampaign, we basically exist to help small businesses grow. So it’s basically a new take on marketing automation, where it’s about being the right stack of tools and orchestrating the customer experience.

But to get to that idea, to get that thesis to the market, took me 16 years, so far. So, I started the company back in ’03, and started with on-prem software, selling to SMBs. So I took two extremely difficult things, combined them together, and did that over a decade.

13 years into it, I go from myself to about 20 people. So not exactly like that fast, explosive growth a lot of people talk about, but a solid business. But then, from that point to now, we’re now over 350 people, adding about a couple hundred people in the last year alone.

Harry Stebbings: Can I ask, what was the … I mean, that’s an extraordinary journey that, as you said, 13 years to 20 people, and now 350 within the last three.

Jason VandeBoom: Yeah.

Harry Stebbings: What was the catalyst to that growth?

Jason VandeBoom: It’s a combination of making that decision to go from on-prem software to SaaS. And then starting to find our fit within a new take on marketing automation. I mean, it wasn’t some giant funding event, it wasn’t some giant explosion of new customers coming in, necessarily, from some paid advertising or something like that. It was just truly genuine value we were providing, and that just started to spread.

Harry Stebbings: Another question I do just have to ask, and sorry, off-schedule. I meet a lot of founders who maybe don’t experience the explosive growth of maybe your Slacks of the world. What advice would you have to them, who are enduring building a solid, sustainable business, but they see the funding rounds, they see the huge ARR numbers. What advice would you have for them?

Jason VandeBoom: Like, they should actually be truly excited about the fact that they’re building a sustainable business. Nobody gives enough credit to people that are doing that. Even in those years where we were only 20-some people, that was actually a really solid business.

And I’d argue probably worth more than some of these businesses that will just take a bunch of capital, and then if that one or two outcomes don’t occur, even getting to like an exit of 50 or 100, or something like that, is really hard. So, I think there’s this envy and this fear, of needing to have this fast growth, that can be somewhat toxic.

Harry Stebbings: For sure, I completely agree. And can I ask: 16 years ago, the venture ecosystem wasn’t what it is today, but it was still there and prominent. Why did you not decide to raise, like more traditional SaaS companies maybe have and did do, in that time?

Jason VandeBoom: One, I don’t think I would have probably been able to raise very easily. Two, I just don’t think it’s something that you should strive for at all. Most things that you have to do early on, as you start building out your sales team, as you start hiring a couple people here and there, you can find a way to pay for that.

So, like, if you create this concept that you need funding to do that, or funding is some form of validation, then that’s just a flawed concept in my mind. There’s plenty of forms of validation you can find outside of funding.

Harry Stebbings: So, for those that say, “I need funding to build out my sales team and to hire my first VP of sales,” what would you say?

Jason VandeBoom: You’re the first VP of sales, so figure it out. You need to be close to that, early on. And then, once you have it half figured out, I’d say try to hire three reps at least, to start. Now, that seems like, “Do you need funding for three people?”

Probably not. You could, possibly, but there’s also ways you can, one, either just generate some revenue. Or figure out how to pay for it in the short term. And if you are building that sustainable business, you have plenty of options beyond just venture funding. So you have a bunch of different options, and ways to make money.

Will it be slightly slower? Perhaps, but if you can keep more of your company, that means you control your destiny more. So, the biggest risk I see for early-stage founders would be to give up too much early on, and that will affect things over time, in a way that you may not like.

Whereas, if you actually get sustainable growth to a certain point, opportunities will come to you. And that’s when you should take funding, is when the opportunities come to you, not when you need them. Because then, you sort of control the situation, and most likely you actually have control of the destiny of the company over time, that means.

Harry Stebbings: Absolutely. I think that leverage is priceless. But so much to touch on that. I do want to break the show up today into a couple of different elements, starting on the market that we’re going after. Then moving to the product itself that we have. And then finishing on, you the founder and the people that make the product. Does that sound good?

Jason VandeBoom: Sounds great.

Harry Stebbings: Okay, so if we start from the top, we have the market. And the common question all founders ask me is on market entry. “Do I go SMB? Or start at enterprise?”

When we chatted before, you said to me, “SMB first works.” So, grabbing the bull by the horns, what leads your thinking here, and why does SMB first work so well, in your mind?

Jason VandeBoom: First off, I love SMBs. I was one, for well over a decade. I still consider us a small business, to an extent. I mean, we’ve worked with tens of thousands of them. So, like, the whole idea of pushing to go enterprise early on sort of bothers me. For some businesses, that works really well, but– For a couple of reasons, why I like SMBs and why I think it’s a good entry point, and to even stay there, would be: it’s easier to start with an idea, a higher volume of points of feedback, and possibly most importantly, you can design for what you’re looking to actually do and achieve.

Meaning you’re not designing for a known need within enterprise. That’ll hardly revolutionize a market or something like that, typically. That’s just solving for a known need.

So, if you have an idea, and that’s a little bit beyond that, starting with the SMB will allow you to do that because you don’t have a single company that’s going to just push you into a direction of their own choosing.

The other thing I’d say is, everyone always say, like, “Don’t design for an outcome,” like an acquisition, IPO, et cetera. I say, “Don’t design for enterprise.” Meaning, go SMB first, allow midmarket enterprise to buy from you, and it gives you a unique advantage in which you can sort of apply pressure to the enterprise space in a way that the space hasn’t seen, or hasn’t requested.

So, if you start with enterprise first, you’re hardly going to shift the way of thinking there. You’re just going to create something that’s known, and likely something that’s similar to something in the space.

Harry Stebbings: No, I couldn’t agree with you more there. And two kind of concerns, or questions that come to my mind, really lie around the ACVs that are inherent within SMB. I have to admit, I’ve been prone to it myself, along with other VCs, that immediately say to founders, “Ugh, with those ACVs, it’s going to take 20,000, 30,000 customers to scale to X number of revenue.”

How do you respond to the common VC statement of, “Ugh, such small ACVs, the difficulty with the go to market, and …” How do you respond to that?

Jason VandeBoom: Well, bluntly, I’d probably just say, “Who cares?” But that’s just … I’ve seen the power of that compounding. And also, if you’re providing that much value and whatnot, midmarket enterprise will start buying from you. That’s always the situation I’d want to be in first, before trying to sell to them. Meaning that, they’re seeing enough value to come down and buy, and you’re not forcing something on them.

Even early on, like when it was just myself and I was in art school and whatnot, I had businesses like IBM, Pixar, Texas Instruments, all buying licenses. I was not going after the enterprise. And half the time, you start within enterprise in a department, or some small organization within it, right?

So, it’s just not obsessing about that. They will come to you. And we’ve seen this with so many other companies that have been SMB first. I think mostly, this push from enterprise is just like, it’s every playbook, it’s every thought. It always goes down to that, “ACVs are terrible.”

Yeah, on a blended basis, your ACV may be low. But you will start finding ways to get some larger AVCs in there, as well.

Harry Stebbings: No, I love that: let midmarket come to you. The other kind of common statement is that the mortality rate of SMBs is so high that your churn is inevitably just going to be so much higher. Is that something that you’ve seen? And how would you respond to that statement from most VCs?

Jason VandeBoom: Yeah, it’s higher, but also there’s more of them. It’s also a market that everyone uses and then leaves.

So let’s say you actually figure out retention. You figure out a way to have 100% plus revenue retention, like we have, with being focused on SMB. That’s a fantastic place to be within, right? Because that means it’s harder.

But if you can figure that out, and if you can provide enough value, and provide enough organic way of customers adopting your platform, you have a unique advantage. And you can use all of that, you can use that momentum. And if your true care is chipping away at midmarket or enterprise, you can use all of that to both fund and create the sort of momentum towards taking on that space.

Harry Stebbings: And speaking of the momentum, you mentioned that the early, big logos that you did have. I do have to ask, you mentioned obviously being the first sales rep yourself, being the founder. What was that incentive to scale out the sales team? Often, people will say “It’s at a million ARR, you’ve got to build out the sales team.”

What was your thoughts around the right time to build out the sales team yourself, and maybe step away from the front-frontline process yourself, as founder?

Jason VandeBoom: That’s a great question. I waited too long, admittedly. So, a couple of things: one, I’ve always been somewhat allergic to sales. So, I wasn’t actually taking my own advice, and actually being the sales leader, to start. We didn’t even have a sales team, for the first decade or so, I’d say.

And with that being said, I found the idea of adding salespeople and stuff … So, the reason I was allergic to it was, I thought that I was the customer, right? And I’m not. So, I was providing the service to our customers, and getting that going sooner, and experimenting more would have been great.

Now, my thought on VP of sales, yeah, a lot of people think about it in terms of revenue, or in terms of customers, or something like that. My take is, I would probably try to run the sales team, and this is kind of what I did, with a sales manager.

So start with three reps at least, then build out a sales team. Once you get like eight or nine people, get a sales manager. I would manage that directly up until about 20 or so people.

Now, the reason for that: the findings from the sales process, it’s going to impact your product direction, literally everything. You want to be really close to that. And despite, maybe you’re a product person or a tech person, and you really don’t want to do that, and you think you’re not great at it. And you might not be the best at it. But you’re probably better than anyone from the outside, for that. So, early on, being so close to that is important.

And then also, if you go and hire a sales rep to create a sales team, I mean you’re expecting to get to 20, or 50, people. The person that starts as your VP of sales at one person may be able to scale up like that.

But more often than not, maybe their sweet spot is in that, like, just starting a sales team and getting in to like 25 or 50. And then you’re going to have to find someone else to help sort of take it further on.

So, being close to that critical customer touch point is really important in my mind.

Harry Stebbings: Speaking of kind of scaling that sales team, Tom Tunguz has written a lot about the required ACVs to justify an inside sales team.

Jason VandeBoom: Yeah.

Harry Stebbings: How do you think about that? Is there a number? Is that kind of one of those arbitrary SaaS posts? Or is there actually kind of some formula behind it, in your mind?

Jason VandeBoom: I get the point there. I think that in general, thinking that there’s some price point you need for a representative, as a blanket statement, is kind of BS. Meaning, just wrong.

Because, even … Let’s say you take an ACV, like I’ve had salespeople sell things down to $3, $400 ACVs. Yes, the velocity there would have to be incredible. But if you find that balance of automation and human touch in the sales process, it can be done.

You’re looking at a little bit more of a transactional sales process, maybe a little bit less heavy touching, less followups. But you can adapt a sales process to just about any ACV.

And now, what I would also suggest is, even if it looks on paper that it doesn’t make a ton of sense, you can find ways to perhaps provide more value, or perhaps sell people a little bit higher on along the way.

So, even if for a while your ACV that they’re selling is pretty low, you’re just getting started. So surely there’s ways you can try to push further, to try to boost that up if that’s important to you.

Harry Stebbings: Absolutely. Couldn’t agree more with you on that, and boosting and upsell. We spoke earlier about the sales team, and the build-out of it. I do want to blend in the element of product, itself. I’m always permanently conflicted by the balance of being product-first with building out the sales team. How did you think about this, and doing it the right way? Let’s start on that.

Jason VandeBoom: I would say you have to start with the product. Because ideally, going back to, “You’re not building something that people are specifically asking for in great detail.” Meaning like, you’re not just a consulting company. You’re building a product, you’re building a platform, that’s hopefully going to shift something in the market, right?

So, start with product. And then, like I said earlier, you are the salesperson to begin with. And it doesn’t matter if you’re terrible at it. If you can’t figure out how to sell your product, and be the salesperson, be the sales leader, you’re going to have so many other different problems along the way of scaling a business that you might as well get rid of that pain right now.

So, once you have things going, maintaining that product-first mentality is kind of hard. It’s very easy to start seeing opportunities in the way of, like, “If I just scale up my sales team and just focus on that, good things will happen.”

But I’ve seen all too often other companies doing that, and you have a good year or two of wild success, everything looks amazing. And then, all of a sudden, there’s a company that’s a little bit more product-first, and product-focused, and they’re able to disrupt you.

So, maintaining that product-first while building a sales team is tricky. I’ve actually had to hold back building our sales team at a number of points, because I don’t want that to allow to happen.

Now, that looks like you’re leaving money on the table, or it looks like … Especially in the investment community, or something, it would look just idiotic to some. But I think long-term, if you truly care about that sustainable business, and building something long-term, it’s really the only route to take.

Harry Stebbings: Can I ask, how do you think about the right communication flow between product and sales? Often, we see tension with sales promising the world to customers, and then delivering it to the engineering team, and [crosstalk 00:16:23]-

Jason VandeBoom: Yeah, yeah.

Harry Stebbings: … product displays that are unheard of. How do you think about the right communication flows?

Jason VandeBoom: I think communication in a not-so-distant future … Meaning, like, it’s okay to have some wild ideas out there, and directions we’re going in. But not the detail where you can sell to it, as much.

Also, it just goes to sales culture and sales team, sales leadership. That’s really where it stops in my mind. And so, we’ve been fortunate to not have to deal with too much of that. But just culturally, and with sales leadership, I think that’s been the reason why.

Harry Stebbings: We’ve spoken a lot about the building out of the sales team, and building out of the product as well. In a lot of cases today, it’s the assumed thinking that that both requires funding. We spoke before about the many options that one has.

But we also spoke before this interview, and you said to me, about optimizing timing for funding. How can I not dive on this one, Jason? What did you mean by “optimizing timing for funding?”

Jason VandeBoom: Kind of going back to like, first off, nobody really cares that you got funding, if you get it. So, don’t really celebrate it. Meaning, the concept that funding is validation, that’s a flawed concept. Your competitors maybe care, maybe a few folks in enterprise, that helps you.

But otherwise, like if you’re SMB, your customers probably are actually kind of scared if you get funding, based on the push to enterprise all the time. So, really find ways to just build things out. Going back to building out a sales team, like you can find a way to pay for three reps, if you’ve already proven out a process.

And do things that just will not scale at all, and do them all the time, and keep doing them, as you grow your business. We do so many things that anyone just looking at it on paper would be puzzled by. But we’re not designing for some short-term need, or trying to optimize some metric, or your KPI, for someone to get some outcome.

We’re doing something based on what we know the value will be over time. And just know that you know more than you probably give yourself credit to. And then, just let it happen. In an ideal situation … It’s not always possible for certain business, but let it happen naturally, and expect it’ll never happen. Meaning, “There’s probably no help on the way.” If you just live by that idea, and it’s just being up to you, you’re forced to build a sustainable business and something you control.

And not to be all doom and gloom with all of that, there is positive with that. When you do that, and if you build that sustainable business, you’re providing unique value, you’re staying really close to your customers, opportunities will come to you.

And when you have them, and they’re not needed, then act on them. If you have opportunities and they are needed, try to find a different way. And using that, if at all possible… It’s not always possible, for some businesses it wouldn’t make sense, but if you can, it’s a very advantageous place to be in.

Harry Stebbings: One other big positive that’s often cited with kind of that big funding announcement is what it does in terms of allowing you to hire the very best candidates. Would you agree with that, or is that maybe an unfair statement to make?

Jason VandeBoom: I think it’s unfortunately partially true, because it provides some form of validation. But going back to my other point, you can get validation from a number of different areas. It doesn’t have to be just that. So, we experienced that ourselves, earlier on, where nobody knew about us. Like, even in the market. So, hiring … And then, if you don’t have that validation of an investor, something like that, it’s a little harder. But, as a founder, or as leadership in a company, it’s your job to be able to sell the product, sell the company, sell the vision. So, if you’re not able to do that, you’re going to have a lot of struggles. So I actually like the idea of being put in that situation, and forced to try to sell the vision enough so that you can find a fantastic leader without having as much external validation.

Harry Stebbings: Absolutely, I completely get you. I almost view it as a crutch that you kind of, a stranglehold as a leader.

Jason VandeBoom: Exactly, yeah.

Harry Stebbings: And so you have to do it without it. Yeah, absolutely.

If we kind of merge everything that we’ve discussed together, though, we have the product, we have the people, and you said before to me that you can never have any form of distance between yourself and customer feedback. It sounds very nice. What does it look like in practice and reality, Jason?

Jason VandeBoom: It’s extremely painful in practice and reality. So, my thought, I am a huge believer in the idea of, as a leader, as a founder of a company, you need to be consuming all feedback in some fashion. And it has to be direct, and not in a summary form. Meaning, whether it be NPS or something like that, actually reading it.

So, despite having 60,000-plus customers, I read all NPS, all cancellations. It’s basically the first thing I do when I wake up and the last thing I do before I go to sleep.

Now, it’s like the worst way to start your day, for how some people would think. But you only get a true sense of where are the pain points, where are you providing value, by looking at that level of detail.

Now, it’s human nature to want to make that easier. So what do we all do? We all create a role, maybe, put someone in that. And they’re going to maybe create a fun report for you, or something. Maybe check that out every couple of weeks, or something like that.

But I’ve done that, I’ve tried to just look at it in batches, things like that. Every time I’ve done that, I’m losing something. I’m losing an understanding of the business, of the customers, of the customer pain points, opportunities, and where value is being seen. And I’m just losing the ability to run the company as efficiently as I should.

So that level of detail, maybe it’s not scalable forever. Plenty of people have told me that already. But like, I’m still okay, I’m still a happy person, and whatnot. That gives you such a unique advantage. And it becomes infectious, as well.

So like, I do this, but now other leaders have started doing that, and it’s been spreading throughout the company, where people want to be able to get all of this raw data in real time, so they can check it out. Which is an amazing cultural thing to happen.

Harry Stebbings: So, I absolutely love that. I mean, I feel sorry for you waking up to do that, but I do have to ask-

Jason VandeBoom: I love it, yeah.

Harry Stebbings: I do have to ask, though, in terms of the communication flow, you get that raw data. You get that feedback. What does that communication flow look like, into the differing segments of the organization, product, sales, marketing, from your kind of raw data ingestion?

Jason VandeBoom: Sure. So, I get a raw data feed of it. We then have people tag some of it, and then it’ll go off to different parts of the organization. And then we also have people working on all of the NPS, cancellation, churners, everything like that, in more of a … Being able to take action on it. I’ll see something, or someone else will see something, we can just kind of note it. And then other people will follow up, and see what the outcome is. And what’s fascinating here is, we’re talking about like … I’ll have discussions with our CTO and others, of an account that’s like $49 MRR. And it’s just absurd to others outside of the company that we’re all spending the time, such a small MRR. But that pain point, and that opportunity, that we’re identifying and caring about the customer experience regardless of ACV, is what creates a truly unique customer experience.

So, I think that’s how you can build something that doesn’t necessarily look right on paper all the time, but it’ll prove to be a differentiator for you.

Harry Stebbings: Jason, listen, I love that. And it’s one of the first times I’ve heard it on the show. I do have to ask, though, with kind of all that raw data, I automatically think of Ford’s statement: “If I made the product that people wanted, I would have made a faster horse.” With so much data coming in, how do you determine between the customer-driven versus customer-informed, and that kind of distinguishing?

Jason VandeBoom: That’s a good point. So, it’s a guiding indicator of just value provided, that’s it. And potential opportunities and whatnot. So, what you don’t want to do is, you don’t want to drive decisions directly from feedback. They’re basically just indicators and little lights of something. Feedback is not your roadmap. If it is, you’re going to be an irrelevant company. But it is going to expose some pain and opportunity. So, what you do with that is more up to. But you should never work directly off of it.

Harry Stebbings: I love that. “Feedback is not your roadmap.” That’s a quote that should be coined.

The final element, though, that I do have to touch on, Jason, is your role as CEO. As we mentioned earlier, an astounding 16 years. Tell me, with that in mind, how does the role of CEO change over time?

Jason VandeBoom: You go through these phases of being tired, and … No, it’s really the … So, I have an obsession of details, and how things are executed. You can’t be as in the details when there’s hundreds of people, apparently. So, influencing that obsession of details throughout the company, messaging your direction, what matters, and whatnot. That’s been the biggest thing for myself to learn along the journey.

Harry Stebbings: Often, it’s cited that it gets easier over time. Is that something that you would maybe agree with, or fundamentally disagree with?

Jason VandeBoom: I’d say some things definitely do. At the same time, whatever was easy and nice before is gone. Like, someone else is doing that, or something like that. So your problems get worse as well. I wouldn’t say it really gets easier or harder, it’s kind of the same level of difficult the entire way. So, probably hard the whole time.

Harry Stebbings: That’s reassuring to hear.

Jason VandeBoom: Yeah, it’s great.

Harry Stebbings: Over the 16 years, there must have been some pretty kind of pivotal moments. What have been some of the core inflection points in the company scaling that you saw firsthand as CEO?

Jason VandeBoom: One was that move and that decision to go from on-prem to SaaS. It wasn’t a sure thing. We were taking a profitable company that was growing and deciding to throw away all the revenue, and start from scratch at $9 a month.

The other I’d say is, when we hit around 150 people or so, not being able to actually truly know people. Like, I know a lot of people, but truly know them? Kind of where they’re trying to go, what they’re trying to do, and be able to actually communicate with them all, on that truly individual level? It just becomes impossible. That was hard for myself to get past that point.

Another thing has been an interesting point of, we’ve always been kind of this underdog, this sort of unknown in the market. As we’ve scaled, as we’ve started taking market share and whatnot, that’s changing. So, just seeing that happen, it’s just been fascinating. And another example of validation that doesn’t require diluting the company.

Harry Stebbings: Can I ask, what was the hardest phase within the journey, for you as CEO? And you seem incredibly calm, logical, rational. How do you deal with the “shit hit the fan” moments?

Jason VandeBoom: I had a wonderful one in my on-prem days. So, 2008, we had the financial thing occur, right? We were only eight people at the time. We started … We made this great decision to have a couple new products. They didn’t really take off as we thought.

So, kind of mid-year 2008, I go on my honeymoon. I come back, and all of a sudden, things are not good. The business is not as sustainable. So, had to just stop paying myself for about a year. Lived off credit cards, things like that. Found a way to do things.

We did some crazy things in that time. The business was never really impacted, employees were never impacted in any way, but we were doing like … We had to even do some consulting work, and whatnot, to get through that phase.

But just taking those things head-on, finding a way, and there’s usually a way, to find a way through things. And then learning from them.

So like, part of that situation caused us to think about our revenue stability, and our growth, and that push to SaaS. It took longer than it should’ve, to make the call, to switch to SaaS from on-prem, but with every challenging thing, they’re actually blessings in a way, ’cause you’re getting something out of it. So you should try to appreciate them, after the fact, once you get through it.

Harry Stebbings: My word. I hope for your composure, one day. It’s pretty incredible to hear. But I do, Jason, want to move into my favorite element of any interview, being the quick-fire round. So, I say a short statement, you give me your immediate thoughts, in about 60 seconds. Are you strapped in?

Jason VandeBoom: Yep.

Harry Stebbings: No man’s land in SaaS pricing: does it exist, or not really?

Jason VandeBoom: I do not believe it exists. I believe that just sounds like a VP of sales that wants to run their same playbook over and over.

Harry Stebbings: Tell me, sales rep productivity: what’s good in your mind?

Jason VandeBoom: So, there’s plenty of things. In my mind, it’s really executional excellence, and caring about the details, and then everything else will trail that.

Harry Stebbings: Multi-year deals that often hailed: are they always amazing, and is there anything to watch for?

Jason VandeBoom: I may be the only person that hates annual and multi-year deals. Like, I love them from a financial standpoint, but I love the pressure of a month-to-month deal. When you have to provide value all the time, and you can’t get lazy.

Harry Stebbings: Yeah, you are on your own on that one.

Tell me, you’re deserted — this one’s a new one, but it’s going to be a good one.

Jason VandeBoom: All right.

Harry Stebbings: You’re deserted on a desert island, and you can take one thing. What would it be, and why?

Jason VandeBoom: Ah, that is a good one. Sounds cheesy, but I guess just family. Sounds like a nice vacation break.

Harry Stebbings: Tell me, let’s finish on: what do you know now that you wish you had known at the beginning?

Jason VandeBoom: The world doesn’t end when you try things. Meaning like, don’t ever impact your existing base, don’t experiment with pricing on them, don’t mess around with your existing customers. But experiment as much as possible, and don’t hold back on ideas with new business. That’s something that we’ve done time and time again, continue to do.

We hold back on things, it’s like this fear of success, almost, that causes it. Like, “If it’s successful, we’ll need X, Y, and Z.” Just try it, and deal with the consequences.

Harry Stebbings: Jason, I think you can tell from how little I stuck to the schedule, but I’ve so enjoyed today. Thank you so much for joining me, and I can’t wait for the exciting future ahead with ActiveCampaign.

Jason VandeBoom: Thanks again for having me. I really enjoyed it.

Harry Stebbings: What did I say? Such an incredible guest, and such an inspiring journey. And if you’d like to find out more from Jason, you can find him on Twitter @JVandeboom. Likewise, we’d love to see you behind the scenes here at SaaStr. You can do so on Instagram @HStebbings1996 with two Bs. It’d be fantastic to see you there.

As always, I cannot thank you enough for your support, and I cannot wait to bring you another exceptional episode next week.

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