Introduction
In this interview, we dive deep into the bootstrapped SaaS success story of Jason VandeBoom, the founder of ActiveCampaign. Starting from a need to pay for art school, Jason built a company that now generates over $100 million in annual recurring revenue. Discover his unique approach to growth, his philosophy on being customer-first, and the strategic decisions that fueled his company’s incredible journey from a small on-premise software provider to a global leader in customer experience automation.
Founder Success Story QnA
How did you get your job?
I got it out of necessity in a way. I started ActiveCampaign not for any like grand vision or anything like that. I was looking to pay for art school at the time and so I was doing consulting. I didn’t want to continue to repeat doing that; I wanted to fine-tune on something, be able to craft something over time. So I created ActiveCampaign and from there, I’ve been able to kind of continue to do what I set out to do so long ago.
Is ActiveCampaign your first business?
Yeah, in a way. And I pause a little bit because when I was 12 or 13, I started doing a bunch of programming and consulting. I would find different businesses where I was growing up and throughout the country where I could just find some work. It initially started with web design, things like that, and grew into more like custom software and custom intranets. So that was my, if you caught that, that was a business. And I always thought of that as a business, but otherwise, ActiveCampaign has been the remainder of my life.
In 2003, what was the problem you were solving and how did ActiveCampaign start?
In 2003, there were fewer options for solving such a problem. We started with contact management, but we solved it with the idea of having someone download software, install it on their server, like a more old-school on-premise sort of way of doing things. We were competing with brands like Lyris at the time. And then as we had customers, we started developing software for whatever need we had. So once we had more support tickets, we built help desk software. Once we wanted to talk to those customers more in real time, we built live chat software. ActiveCampaign for the first 10 years went from one to eight products, all on-premise products, but all having a focus on the customer and automation.
When did you move to the SaaS model?
We were fully switched over as a company by 2016. We started thinking about that and started figuring out how to transition before that, but we spent so much time. We could have done it sooner, and with the compounding nature of SaaS, we would even be in a different state today if we did that sooner. I like to not think about that too much.
How come it took so long to come to the SaaS conclusion?
We had a solid business. We started offering some versions of SaaS prior, so we were dabbling with it. If you only ask your customers what to do, oftentimes you end up at a result that’s not best for your business or, more importantly, for themselves. Our customers were looking to save time and save money. The greatest challenge we had was they thought a recurring subscription would cost them more, but they weren’t valuing their own time. So as we were trying to work with our customers and bring them over to SaaS, it was an education and marketing experiment of helping articulate to them what their time is worth.
Have you guys raised any VC?
Yeah. So late 2016, we did a Series A of $20 million. Just more recently, we did a Series B of $100 million. So we have, but in a different way of not wanting to put ourselves into a spot where we had to, and also not wanting to put ourselves into a spot where we couldn’t pursue what we thought was best.
Would you be able to give any numbers around traction, revenue, users?
We just passed a hundred thousand paying active companies, which is pretty exciting for us. And we’re over $100 million in annual recurring revenue. So it’s a lot of hundreds going on lately for us between our Series B and all that stuff.
After 13 years of slow growth, what changed to spark this insane growth from 2016 to 2019?
It wasn’t one person. We couldn’t have done any of this without an amazing group of people. The realization by building out each of these individual tools was that we wanted to make ourselves more efficient through automation. We started doing that in every single little piece, and that created this view of, “What if we could do this across everything?” We made the decision to go from eight products to one and switch that over to software as a service. That led to this idea of focusing on contacts, customer data, automating the entire customer experience. As we started going, it really started to resonate, helping us create that growth.
Why did you decide to raise capital?
Later in 2016, we were already seeing a ton of momentum; we didn’t have to. But that was always key: I wanted, if we were to raise, to not be at a moment where we had to. I also wanted that outside pressure, even if they can’t necessarily control decisions, just to make them sad or have someone questioning ideas and questioning what we’re doing. I thought there would be value there. Looking back, could we have done everything without raising? Yeah. But at the same time, they’ve added a ton of value, and I wouldn’t take any of it back.
Can you delve deeper on customer-first versus product-first?
If you only focus on product, it creates a lot of issues. In my mind, by focusing on being customer-first, you do need a product that a customer can use. It’s how can you provide more of that partner feel to a business. We’ll do things that are ways to grow that your peers may not be able to do. We offer free migration, free strategy sessions. If you only focus on the product, you almost think of your customers as a second to that. It’s just switching that order. It’s the rest of the company where it matters so much. It’s that constant drumbeat of surfacing true actual conversations with your customers instead of just getting dashboards and reports.
If you don’t do what customers say for product development, how do you know how to build a great product?
You should have some thought or conviction around what you’re trying to solve at a super high level. If you only look at directly what your customers are asking for, it’s probably going to mirror what’s on the market. On top of that, you’re looking at all your competitors and thinking that’s the direction you have to go in, which stifles your ability to innovate. It’s not that you don’t care about your customers; it’s not that you won’t solve what they’re asking for. It’s just trying to do it in a way that isn’t necessarily exactly how they prescribe it. Sometimes that’s innovation.
You’re proud of not doing typical marketing. Can you elaborate on that?
If you’re trying to solve customer experience automation, the differences that exist for a small business, a mid-market, and enterprise are different. I don’t think you actually have to move up market. We always have automation accessible all the way down to like nine dollars a month, and that’s key because every business at some point is a small business. The fact that we have a hundred thousand companies using our platform is an amazing growth vehicle. Most of our traffic, most of our growth comes in organically because we’re focused on trying to help small businesses be successful, so they become those advocates.
How did you manage going from 20 to 600 people in a few years?
It’s been a little bit of learning. Part of it goes back to controlling the growth however we could. It’s always felt like a little bit of catching up to momentum. Finding how you can stay ahead, how you can help people internally become the leaders for the next phase. When you’re growing that quickly, the next phase could be very soon. Building out support throughout, and taking that same customer-first mentality and trying to take that internally as well. There’s been times where we sort of pause or slow down and let the organization catch up.
Have you been able to have your people ready for different stages of growth or have you had to bring in trained executives?
It’s a bit of a mixture, and I think that’s probably a healthy way of doing it. I don’t think we could do it all internally because at some point, you have to hire and gain different perspectives. While we’re being small business first, I want people with a mid-market or enterprise mindset. I want people to be pushing on all different ideas from different directions at the same time. Building that culture of just questioning is something you just have to reiterate and also be okay when people do that.
Did you expect when you raised that Series A that you guys would grow this fast?
No, not to the degree we have. I don’t think I’ve ever fully expected that. You’re always kind of in the moment. At any given stage, especially then, we were so much in the building of the business it was hard to step outside of that. We were seeing momentum before raising, and that’s part of the reason why we did, so we knew we were onto something. But it’s the ability to work with all of these amazing people, that network, that’s been a big growth area for myself as well.
What’s exciting for you in the future?
We’ve been over 55% international in terms of customers for quite some time. Within the last year, we’ve started to build that out with more focus and are seeing tremendous results. That’s exciting. Also, what we’re doing in terms of how do we make automation even more powerful and faster for people. How do we make it so that no two customers with a brand share the same experience? We have a lot of innovation that we’re going to continue to bring out, and that’s a really exciting area where we can be there for a business and deliver a personalized experience that the consumer actually likes and expects.
What would be your parting words of wisdom for early-stage startup founders?
I would just trust your instincts a little bit and allow some time. The problem that exists all too often is we see playbooks, we see stories, we see outliers, and we think we have to mold to that to create traction or growth. All too often, that can lead you down the wrong path. I think it’s really trusting your instincts on that a little bit and trying to find a path that is a little bit differentiated. Maybe it takes a little bit longer, maybe it’s not going to get that news article in year one or even year ten, but if you are passionate about it, enjoy it, and have that strength to find your way through that, go for it.
Jason VandeBoom Business Stats
Jason VandeBoom’s journey with ActiveCampaign is a masterclass in sustainable, long-term bootstrapped SaaS success. The company has achieved remarkable scale by focusing deeply on customer needs and leveraging organic growth. Below are some of the key statistics that highlight the impressive state of the business today.
- Achieved over $100 million in Annual Recurring Revenue (ARR).
- Serves more than 100,000 paying active companies globally.
- Grew the team from just 20 to 600 employees in roughly four years.
- Successfully bootstrapped the business for 13 years before taking external funding.
- Raised a total of $120 million in venture capital (Series A & B).
- Maintains a strong international presence, with over 55% of customers outside the U.S.
| Metric | Value |
|---|---|
| Annual Recurring Revenue | Over $100 Million |
| Paying Customers | 100,000+ Companies |
| Team Size | 600 Employees |
| Year Founded | 2003 |
| Total Funding | $120 Million |
Jason VandeBoom Method
The core of Jason’s method is a steadfast commitment to being customer-first rather than product-first. This philosophy guided every major decision, from the initial product development to the strategic pivot to SaaS. He focused on building a partner relationship with customers, which in turn drove innovation and sustainable growth.
- Started with on-premise software to solve immediate customer needs.
- Built multiple products (help desk, live chat) to understand the entire customer experience.
- Made the bold decision to consolidate from eight products to one unified SaaS platform.
- Prioritized customer feedback for insight, not as a direct product roadmap.
- Focused on organic growth by making customers successful and turning them into advocates.
- Maintained optionality by not relying too heavily on any single customer or investor.
Jason VandeBoom Tools
While Jason doesn’t list a specific tech stack for running the business, his primary “tool” is his company’s own platform, ActiveCampaign. Beyond the software itself, he leverages specific strategies and services to execute his customer-first vision and drive growth without heavy reliance on traditional paid marketing.
- ActiveCampaign: The central platform for customer experience automation, used to power their own business.
- Free Migration Services: A tool to lower the barrier to entry for new customers switching from competitors.
- Free Strategy Sessions: Used to understand customer needs deeply and build advocacy, even for non-paying users in the past.
- Customer Success Team: A human-powered tool to ensure customers get value and act as true partners.
- Organic SEO & Content: The primary engine for new user acquisition, focusing on providing value over advertising.
Key Notes
The interview with Jason VandeBoom reveals several counter-intuitive yet powerful insights for building a enduring business. His story challenges the conventional “move fast and break things” mantra, proving that a deliberate, customer-centric approach can lead to extraordinary outcomes. Here are the most critical takeaways from his journey.
- A customer-first culture is more impactful than a product-first one.
- Don’t just follow customer requests; innovate based on the underlying problem.
- Bootstrapping for over a decade provided the freedom to find the right path without external pressure.
- Organic growth driven by customer success is a powerful and sustainable moat.
- It’s okay to grow at your own pace; building the right foundation is crucial for long-term scale.
- Raising capital should be a strategic choice for optionality, not a necessity for survival.
Get Started in Just 5 Steps
Inspired by Jason VandeBoom’s bootstrapped SaaS success? Here’s how you can apply his core principles to start and grow your own business. This roadmap focuses on building a strong, customer-centric foundation that can scale sustainably over time.
- Start with a Real Problem: Begin by solving a genuine need for a specific group of customers, just as Jason did with contact management.
- Listen Deeply, Don’t Just Obey: Use customer feedback to understand their core challenges, but innovate your own unique solution instead of just building what they ask for.
- Build for Partnership, Not Just Transactions: Offer services like free migrations or strategy sessions to build a deeper relationship and turn customers into advocates.
- Focus on Organic Channels: Prioritize SEO, content, and customer referrals to create a sustainable growth engine that isn’t dependent on a large ad budget.
- Maintain Your Optionality: Avoid becoming too dependent on one client, one investor, or one playbook. Preserve your freedom to pivot and innovate when the right opportunity appears.
Conclusion
Jason VandeBoom’s journey from a solo founder to the CEO of a $100M ARR company is a powerful testament to the bootstrapped SaaS success model. His unwavering focus on the customer, willingness to make bold strategic pivots, and patience to grow at his own pace offer invaluable lessons for any entrepreneur. By prioritizing long-term value over short-term gains, ActiveCampaign has not only achieved incredible financial success but has also built a beloved brand and a product that truly empowers its users. His story proves that with the right mindset, you don’t need to follow the conventional playbook to build a world-class business.