SaaS Interviews with CEOs, Startups, Founders
From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
03 Dec 2025
Chapter 1: How did Club Caddie scale from $450K to $9M ARR?
Back in 2020, what were you at in terms of revenue? Our revenue was only $450,000 in 2019. Going from half a million in revenue to $9 million in revenue in five years is pretty darn impressive.
Ended up selling Club Caddy to Constellation in 2020. CSI is the largest acquirer of vertical market software companies in the world. On average, we look for about an average of 15,000 ARPU per unit.
Fast forward to today, how many customers are paying you today to use the software? 600 and growing by about 25 every month. $15,000 plus ARPU or ACB target, you just told me, times the 600 customers you just shared, that would put you at about a $9 million in ARR today. Would it have been the top like one or two growth channels for you? You know, we've just gotten better at it.
All right, folks, I'm here today with Jason Pearsall. He's the founder and CEO of Club Caddy, a leading golf course management and software company. He's a lifelong entrepreneur and golf course owner operator. He blends this technology, data, and real-world golf operations to help the facilities grow their revenue, improve efficiency, and deliver exceptional golfer experiences across the country.
Chapter 2: What was the strategy behind building a vertical SaaS ERP for golf courses?
Jason, you ready to take us to the top?
Yeah, Nathan, thanks for having me.
The margin profile on running a golf course versus the software for the golf course are very different. They can be. Yeah. I mean, yes. For you, which came first as we get some of your backstory here? Were you an owner operator first or did you build the software then buy a golf course?
Yeah, that's an interesting backstory. So my father was a country club general manager. I worked at a golf course my entire life. After college, I got involved in early stage startup. We had an exit and I bought a golf course. Then in operating our golf course, recognized that
There wasn't a SaaS solution that was designed to handle a club like we had purchased and started building a SaaS solution in 2015 that became Club Caddy and is Club Caddy today.
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Chapter 3: How did Jason Pearsall raise $600K before the acquisition?
That's great. Okay, so before we get the full backstory, I don't want to bury the lead. Can you tell us sort of what's the average price point customers are paying you today and what are they paying? What's the software delivered to them?
Yeah, so it's an entire ERP system for golf courses, which would include, obviously, things like point of sale and inventory and employee management, but also tee time reservations and membership management and their mobile apps and websites and web apps and everything associated with everything it takes to run and manage a golf course. So that's what we build. Golf courses vary, right?
Some golf courses may have... four restaurants and two bars and six different properties. And some golf courses might have nine holes in a snack bar and one counter. And so the profile on a golf course could range somewhere between a couple thousand dollars and tens of thousands of dollars a year in SAS, depending on the scope of the services that they use.
Okay. Okay. Would you say if I was going to force you to go into like an average, would you say your typical customers like in that $4,000 to $6,000 per year price range?
They're higher than that.
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Chapter 4: What role did data-driven outbound and SEO play in growth?
And so on average, we look for about an average of 15,000 ARPU per unit, yeah.
Per year. And which of these, I've got your screen, your website shared right now. I have your products all listed here. Which one's your bestseller?
Well, you can't just use one without the other, right? And so each of these products exist into a single app. And so it's one app with all of these that we just turn on in the back end for them to work together. And so if you're going to book a golf outing at a golf course, that's going to include food and beverage elements, scheduling out rooms so that, you know, that room's not double booked.
It's going to include accounting GL codes that have to be hit. And so The complexity of a golf course is that it's many small businesses and one that all have to operate and communicate together under a single customer profile.
And take me back to the year you launched the business and how you got your first couple of customers. Obviously you were your first customer, but besides you, how'd you get your second and third?
Yeah.
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Chapter 5: How did Jason structure the deal with Constellation Software?
When you build vertical market software, it helps when you are already connected to that industry, right? So I owned a golf course. I had other golf course owners and operators who were within my network and, you know, we bounce and trade ideas and I would talk to them about their pain points and their, you know, their difficulties and,
I ended up a couple of general managers that were early users of my software eventually became the early employees of Club Caddy. And so, you know, it started off through conversations and really understanding what the pain points were that other golf courses that we wanted to service were going through.
And then once we had a pretty good understanding of our own pain points and also having validation and learning other ones that other golf courses were going through, it gave us, you know, endless opportunity to build product to solve it.
Was there early on in those initial years in the 2017-2018 timeframe, was there a lot of other competition? Or, I mean, it sounds like you used some of the competitors. There were things you didn't like, so you built your own. What were some of the things you didn't like?
Look, when we went into it, there's a lot of competition. People want to build golf software. And so when we went into it, there were mature competitors. solutions for full clubs, not just like a golf course with a point of sale and a tee sheet, but needing, you know, events and weddings and restaurants and dining reservations and all kinds of other other apps as well.
There were mature solutions that were server based.
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Chapter 6: What factors influenced the pricing strategy at Club Caddie?
There were the first wave of cloud solutions that were not yet mature in their depth. And that was our vision was we need to stand out. We've got to be different than everybody else. And so we need to build the first mature cloud solution that services a full club.
And so, you know, because there was competition, we couldn't just jump in and, you know, really distinguish ourselves just by building where our competitors were. So we carved out our niche, figured out where we thought the market was underserved and focused on that.
Interesting. And you could also say, look, the reason our own golf course is doing so well is because we use our software, right? If you want to perform well, you use our software as well. We're building learnings into the platform.
Yeah, look, I mean, it certainly helps, but I don't think that somebody's as persuaded as like, I use this at my golf course, so you should too, you'll make more money. Like, I mean, it's too easy to cook the books on like a case study, right?
So the real validation comes from, you know, golf courses, we have no relationship with having that same success and then being able to demonstrate that that is a formula we can repeat elsewhere.
So that was the first year or two. Fast forward to today, how many customers are paying you today to use the software?
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Chapter 7: How does Club Caddie utilize answer engine optimization (AEO)?
600 and growing by about 25 every month.
Oh, wow. And are those all U.S. based or is it all around the world?
To clarify, in the golf industry, you typically will only make a software transition during the winter or during your off season. So this time of year, we're growing around 25 a month. In the summer, those numbers are much smaller. And sorry, your follow up question, Nathan? Yeah, no, follow up question is, are you geographically bound to just the U.S. or is it worldwide?
We currently service Canada. It's a new market that we entered last year. So a little bit more of a limited scale. Conversion rates aren't entirely favorable for SaaS companies. And so when you have pent up demand, the most valuable dollars are coming from the U.S.
Chapter 8: What lessons did Jason learn about enjoying the entrepreneurial journey?
And so, you know, it doesn't make sense to take on Canadian clients. And we have a backlog of U.S. clients trying to get onto our platform. Eventually, you know, we'll tap our market and probably start focusing more on international. But from a maturity standpoint, we still got a long way to go before we've penetrated our ICP base.
And Jason, can I take the $15,000 plus ARP or ACB target you just told me times the 600 customers you just shared? That would put you at about a $9 million in ARR today. Is it accurate?
Yeah, pretty close. A little over that. Okay, very. You're familiar with obviously deferred revenue. And so, you know, we have more clients. Anyways, it's pretty close. Growing though.
Yeah, that's great. That's great. So now that we know 600 customers, 9 million of revenue, have you bootstrapped this from scratch or did you raise a bunch of capital?
Tried to, almost went broke doing it. Ultimately, 2015 to 2019, friends and family covered it myself. And we got to a certain level where we needed more significant investment to handle the opportunity. And so we signed a 50-course multi-course operator. Then they were called Brown Golf. Now they've merged and they've become Great Life Golf.
And we didn't have the infrastructure to, you know, go across the country and implement all of these over a week or two. And they needed custom development that exceeded, you know, then a fairly small dev team. And so had raised and gotten committed. I think it was like 300,000 short of my series A.
It started off with a $600,000 seed round that I funded a good portion of, then went to raise a $2.5 million Series A, had raised about $2.2 million. And an organization called Constellation Software out of Canada, you know, approached us about an acquisition and, you know, happy to tell that story, but ended up selling Club Caddy to Constellation in 2020.
They hired me and I worked for them today.
Oh, interesting. Okay. So I didn't, I didn't pick up on that. So we know Constellation actually like very, very well. We've interviewed many CEOs that now work for them. So you're part of obviously that larger organization. Let me go back to before they acquired you, just to be clear, that acquisition happened, you said in 2016, 2017? 2020. Oh, it was in 2020. Okay.
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