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Founder Interview

How Club Caddie Grew from $450K to $9M ARR with 600 Customers (Interview with CEO Jason Pearsall)

Interview Date
December 4, 2025
Interviewee
Jason PearsallFounder and CEO
Watch
Watch the full interview on YouTube

Company Metrics at Interview Time

ARR

$9,000,000

Customers

600

Avg Contract Value

$15,000

New Customers per Month

25

Revenue at Acquisition (2019)

$450,000

Historical Snapshot

These numbers were reported by Jason Pearsall during the interview recorded in December 2025 and are a historical snapshot, not current figures. See Club Caddie’s current numbers.

Key Takeaways

  • 01Club Caddie reached $9,000,000 in ARR as of December 2025
  • 02The company serves 600 paying golf course customers and adds roughly 25 new customers per month during the off season
  • 03Average contract value is $15,000 per customer per year
  • 04Revenue grew from $450,000 in 2019 to $9,000,000, a 20x increase in approximately five years
  • 05Club Caddie raised only $600,000 in seed funding before being acquired by Constellation Software in 2020
  • 06Jason Pearsall holds the longest earnout in Constellation Software history, extending well into the 2030s
  • 07The company targets an ICP of 7,000 to 8,000 golf courses in North America out of roughly 15,000 total
  • 08Brown Golf (now Great Life Golf) was the first major multi-course operator customer, signing on in 2019
  • 09Top growth channels include review sites such as Capterra and G2, account-based marketing, trade shows, Google Ads, and acquisitions
  • 10A Golf Follies Instagram channel launched in October 2025 drove daily golfer visits to Warren Valley golf course within 45 days

Company Metrics at Time of Interview

MetricValueSource
ARR (2025)$9,000,000Founder interview, Dec 2025
Revenue (2019)$450,000Founder interview, Dec 2025
Customers (2025)600Founder interview, Dec 2025
New Customers per Month (off season)25Founder interview, Dec 2025
Average Contract Value$15,000Founder interview, Dec 2025
Seed Funding Raised$600,000Founder interview, Dec 2025
Series A Target$2,500,000Founder interview, Dec 2025
Series A Committed Before Acquisition$2,200,000Founder interview, Dec 2025
Year Founded2015Founder interview, Dec 2025
Acquisition Year2020Founder interview, Dec 2025
Golf Courses in North America (market size, cited in talk)15,000 (industry stat, cited in talk)Founder interview, Dec 2025
ICP Golf Courses in North America (cited in talk)7,000 to 8,000 (industry stat, cited in talk)Founder interview, Dec 2025
Founder Age41Founder interview, Dec 2025
Instagram-Driven Golfers per Day (Warren Valley)4 to 8Founder interview, Dec 2025
Estimated Revenue per Foursome (Warren Valley)$250Founder interview, Dec 2025

Growth Breakdown

Revenue

Club Caddie grew from $450,000 in revenue in 2019 to $9,000,000 in ARR by December 2025, representing roughly a 20x increase in five years. The average contract value of $15,000 per golf course per year drives the bulk of that figure across 600 paying customers.

Customers

The company had 600 paying golf course customers as of December 2025 and was adding approximately 25 new customers per month during the winter off season. Growth is seasonally concentrated because golf courses only switch software during their off season.

Team and Operations

Club Caddie operates a full BDR team that touches every golf course in its target list every quarter, reaching multiple contacts within each facility. The team manages both inbound and outbound channels and uses HubSpot to track lead source and origin.

Funding and Ownership

The company raised $600,000 in a seed round from 2015 to 2019, then was acquired by Constellation Software in 2020 before closing a planned $2,500,000 Series A. The deal was structured with a small upfront cash component and a long-term earnout that Jason Pearsall described as extending well into the 2030s.

Growth Strategy

Account-Based Marketing and Direct Outreach

Club Caddie maintains a database of every golf course in North America, including the software each course uses and when contracts expire. BDRs contact every golf course every quarter, reaching multiple contacts within each facility to go wide and deep in the organization.

Review Sites and Paid Search

The company invests in placement on Capterra and G2 to capture buyers actively researching golf management software. Google pay-per-click advertising on high-intent, ICP-specific keywords complements the review site presence.

Trade Shows and Live Events

Club Caddie attends golf industry trade shows and physically visits golf courses on a regular cadence to build relationships with operators who prefer in-person communication.

Inorganic Growth via Acquisitions

As part of the Constellation Software model, Club Caddie pursues acquisitions to add customers and capabilities. Winning a single multi-course operator deal can add 100 accounts at once, which Jason Pearsall cited as a significant fuel of growth.

Answer Engine Optimization and SEO

After the Constellation acquisition provided capital, Club Caddie invested in SEO and structured data schema to rank for vertical-specific keywords. The team now also targets answer engine optimization, working to appear in ChatGPT and similar AI search results when buyers ask for the best golf management software.

Best Quotes

Our revenue was only 450,000 in 2019.
600 and growing by about 25 every month.
On average, we look for about an average of 15,000 ARPU per unit, yeah.
I was tired. And what I mean by tired is not like I wanted to I didn't want to grind for the company. I wasn't sleeping because I had staff to pay. I was running around spending time with investors and not in the operations of my business.
I have the longest earnout in CSI history. You know, I don't want to get too far into the details, but I'm incentivized for the long term success of the business. And well into 2030s, we'll be getting my ROI on the sale to CSI.
When you have a very small niche, it's all about data, and it's all about knowing how to action the data. And so we're very intentional about approaching golf courses that have high signals that they're going to be making a transition.
The big one is automated engine optimization. So we intentionally are making investments to make sure when somebody asks ChetGPT what the best golf management software is, they're finding us, right?
Cannot believe it. It's been incredible. Like we thought we'd build we'd get this story out and build a pipe for it and benefit from it in spring. We rolled it out in October, the end of October, and all throughout November, every single day, we had golfers coming in asking about the Instagram page or mentioning the Instagram page.
Enjoy the journey. I always wanted the outcome, to get to where we're at, you know, now. And truthfully, like, the days are easier now, but they're not as fulfilling and they're not as fun.
There's 15,000 golf courses in North America. Seven eight thousand are within our ICP. Ultimately, three to four contacts per golf course. There's 35,000 people that we need to get in contact with them multiple times a year. With strategy, time, and resources, that's not a challenge to do.

What Happened Next

This interview captures Club Caddie at a specific moment in December 2025, when the company reported $9,000,000 in ARR and 600 customers under Constellation Software ownership. Jason Pearsall noted the company was still early in penetrating its North American ICP and had only recently entered Canada as a new market. For current revenue, customer count, and product updates, visit the Club Caddie company profile on getLatka where live data is maintained.

View Club Caddie’s current profile and metrics

Full Transcript

Revenue snapshot and teaser

Nathan Latka

00:00Back in 2020, what were you at in terms of revenue?

Jason Pearsall

00:02>> Our revenue was only 450,000 in 2019.

Nathan Latka

00:05Going from 500,000 of revenue to 9,000,000 of revenue in fiber is pretty darn impressive.

Jason Pearsall

00:09>> Ended up selling ClubCADDI 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 yet.

Nathan Latka

00:20Fast forward to today, how many customers are paying you today to use the software?

Jason Pearsall

00:24>> 600 and growing by about 25 every month.

Nathan Latka

00:27$15,000 plus ARPU or ACV target you just told me times the 600 customers you just shared, that would put you at about a $9,000,000 in ARR today. What have been the top, like, one or two growth channels for you?

Jason Pearsall

00:37>> You know, we've just gotten better at

Guest introduction: Jason Pearsall and Club Caddie

Nathan Latka

00:39Alright, 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. Jason, you ready to take us to the top?

Jason Pearsall

00:59>> Yeah, Nathan. Thanks for having me.

Nathan Latka

01:01The margin profile on running a golf course versus the software for the golf course are very different.

Jason Pearsall

01:06>> They can be. Yeah. I I mean, I yes.

Nathan Latka

01:09For you, which came first as we get some of your back story here? Were you an owner operator first, or did you build the software then buy a golf course?

Jason Pearsall

01:16>> 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, 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 started building a SaaS solution in 2015 that became Clubcaddy and is Clubcaddy

Golf course owner versus software founder backstory

Jason Pearsall

01:45>> today.

Origin story: building Club Caddie from 2015

Nathan Latka

01:46That's great. Okay. So before we get the full backstory, I don't wanna 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?

Jason Pearsall

01:56>> 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

02:26>> golf courses might have nine holes, and 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 SaaS, depending on the scope of the services that they use.

Nathan Latka

02:40Okay. Okay. Would you say if I was gonna force you, though, into, an average, would you say your typical customer's, like, in that 4 to $6,000 per year price range?

Product overview: ERP for golf courses and pricing

Jason Pearsall

02:47>> They're higher than that. So Okay. On average, we look for about an average of 15,000 ARPU per unit, yeah.

Nathan Latka

02:56Per 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 best seller?

Jason Pearsall

03:02>> 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 that room's not double booked. It's going to include

03:23>> 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.

Nathan Latka

03:35And 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 did you get your second and third?

Jason Pearsall

03:45>> Yeah. 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 we'd bounce and trade ideas, and I would talk to them about their pain points and their difficulties. I ended up a couple of general managers that were early users of my software eventually became the early employees of Club Caddy. And

04:12>> so 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 understanding of our own pain points and also having validation and learning other ones that other golf courses were going through, it gave us endless opportunity to build product to solve it.

Nathan Latka

04:34Was there early on in those initial years, in the 2017, 'twenty eight 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?

Jason Pearsall

04:46>> Yeah, 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 solutions for full clubs, not just like a golf course with a point of sale and a tee sheet, but needing events and weddings and restaurants and dining reservations and all kinds of other apps as well. There were mature solutions that were server based. There were the first wave of cloud

05:12>> 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 because there was competition, we couldn't just jump in and really distinguish ourselves just by building competitors were. So we carved out our niche, figured out where we thought the market was underserved, and

05:38>> focused on that.

Getting the first customers through industry network

Nathan Latka

05:40Interesting. And you could also say, look, the reason our own golf course is doing so is because we use our software, right? If you want to perform well, you need to use our software as well. We're building learnings into the platform.

Jason Pearsall

05:50>> Yeah. Look, 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 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.

Nathan Latka

06:12Mhmm. So that was the first year or two. Fast forward to today, how many, customers are paying you today to use the software?

Jason Pearsall

06:19>> 600 and growing by about 25 every month.

Nathan Latka

06:22Oh, wow. And are those all US based, or is it all around the world?

Jason Pearsall

06:25>> 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?

Nathan Latka

06:37Yeah, no, follow-up question was, are you geographically bound to just The US, or is it worldwide?

Jason Pearsall

06:41>> We currently service Canada. It's a new market that we entered last year. Still 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 US. And so, you know, it doesn't make sense to take on Canadian clients when we have a backlog of US clients trying to get onto our platform. Eventually, you know, we'll tap our

07:08>> 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.

Competitive landscape and carving out a niche

Nathan Latka

07:17And Jason, can I take the $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 $9,000,000 in ARR today? Is that accurate?

Jason Pearsall

07:27>> Yeah, pretty close.

07:29>> A little over that. Okay. You're familiar with obviously deferred revenue. And so, you know, we have more clients. Yeah. Anyways, it's pretty close. Growing though.

Nathan Latka

07:39Yeah. That's great. That's great. So, so now that we know 600 customers, 9,000,000 of revenue, have you bootstrapped this from scratch, did you raise a bunch of capital?

Jason Pearsall

07:48>> 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 go across the country and implement all of these over a week or two.

08:21>> And they needed custom development that exceeded 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 $2,500,000 Series A. I had raised about 2.2. And an organization called Constellation Software out of Canada approached us about an acquisition. And, you know, happy to tell that

08:52>> story, but ended up selling Club Caddy to Constellation in 2020. They hired me, and I worked for them today.

Nathan Latka

09:00Oh, 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, and I'll 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 twenty sixteen, twenty seventeen? 2020. Oh, it in 2020. Okay. You said that you almost I think I heard you right. You said

09:22you almost went bankrupt in 2015, 2016. Did you ever think about shutting the business down?

Jason Pearsall

09:26>> No. It was no, 2019. And it wasn't almost going bankrupt. It was just like I was having more go out than I could afford to go out for an extended period of time. And I knew that if we didn't either raise capital or figure out a long term solution, that eventually that would be where we were headed. But we weren't close to I shutting down the was just maybe dramatizing that we didn't I couldn't afford to

09:50>> support the business by myself or continue to bootstrap the business by myself.

Nathan Latka

09:54Okay, fair enough. But so before that, you just raised the $600,000 seed yourself and the 2,100,000 or $2,200,000 from other folks. That's all you raised before the CSI acquisition?

Jason Pearsall

10:02>> I only raised 600 k before the CSI acquisition. We raised a 600 ks seed round that got us to about 2019. In 2019, I started fundraising a series A and spent about fifteen months getting check commitments and almost had the round closed, then Constellation came into the picture.

Customer count, geography, and seasonality

Nathan Latka

10:21Oh, I see. Okay. Tell me that story. Because a lot of founders, when they're thinking about just their capital like, story, their capital stack, they go, man, today, right now, I'm raising capital. But what a lot of folks don't realize is if you're gonna do a data room and do all the work already, you might as well talk to buyers and equity investors and pit them against each other to get what you want as the founder.

10:39Is that what happened here? And and if not, tell us what did happen with CSI. Why'd you sell to them?

Jason Pearsall

10:43>> So CSI is the, for especially people who may not have the background, is the largest acquirer of vertical market software companies in the world. They own 2,000 other brands and labels like Clubcaddy. They're all either top or one or two in the specific vertical that they service. So hospitals, legal, hotels, yacht clubs, every vertical needs software.

11:10>> Constellation Software is the market leader in private club software globally. They have 55% market share. And they had one of those legacy solutions that I had mentioned there were mature server based solutions. There were immature, cloud based solutions. And we were the first full, club based management software that was cloud based. And so there were really good synergies for together, one plus one could equal three, because we had the next generation product, and they had the

11:38>> majority of market share. And so, you know, because the deal was structured right, we set it up so that we both won off of that opportunity of it just made more sense, and there was the possibility, at least, for more upside, you know, by selling to CSI.

Nathan Latka

11:55Mhmm. And what you know, most most of the deals CSI do does you know, the the the knock on that, if there is a knock, is founder will say they close really fast, but they're not paying premium valuations. Right? So in around that time period, you sent around 9,000,000, 10,000,000 revenue today. Back in 2020, what were you at in terms of revenue?

Jason Pearsall

12:13>> Yeah. Our revenue was only 450,000 in 2019. So

Nathan Latka

12:18Oh, wow. Okay.

Funding history and the road to Constellation Software

Jason Pearsall

12:19>> Yep.

12:24>> And CSI does a lot of deals, right? There's 2,000 companies, and some of those have worked out really well for founders, and some of those haven't worked out well for founders. And it all depends on your position, right? A company that CSI is likely to buy is a company that has gone through a growth period, started to decline, the founders are getting tired, and likely best practices for running the business for installs. There's opportunity to come

12:48>> in, run the business more efficiently, and increase earnings, and regrow that company with new energy and new investment. Our situation was a little bit different. We are the earliest stage company that Constellation's ever acquired. They only acquired us based off of the synergies between they were the market leader in golf, they needed a solution like ours, and we had it. And so, I have the longest earnout in CSI history. You know, I don't want to get

13:11>> too far into the details, but I'm incentivized for the long term success of the business. And well into 2030s, we'll be getting my ROI on the sale to CSI.

Nathan Latka

13:24That's fair enough. Okay. Are you comfortable sharing just the cash component at close? Was it like 40%, 50% of the deal price? Or what's that look

Jason Pearsall

13:31>> It was a fraction of the deal price. It was make everybody whole plus some, especially the early stage investors. And the majority of the consideration would be structured around the long term earn out of the company.

Nathan Latka

13:46Okay. So if I'm reading between the lines again, you can only say so much. So I'm trying to be respectful of what you can and can share, but you're doing about 500,000 of ARR in 2019. You've raised 600 k up to that point. CSI was a great home for you because they had old software. You were the new sexy shiny object. You had what they wanted. Smallest deal they've done, but again, you had the tech plus

14:03they wanted you. You know, they did enough upfront cash to effectively make the 600 ks already raised whole, but then incentivize you to stick around long term to grow this thing, which you have. It's grown from 500,000 to 9,000,000 of revenue over the past five years. Is all that about accurate?

Jason Pearsall

14:17>> Yeah, ultimately, they gave the investors, and a lot of the investors, the opportunity to continue to participate in the upside of the earn out, or be bought out in a nice ROI on the short term investment they had made, and the majority of the investors said, we're going along for the ride. And so they didn't have to pay a ton, but they had to commit a good chunk of revenue for a long period of time to

14:36>> get the technology.

Nathan Latka

14:38And what were you thinking in 2019? I mean, you had good momentum on the series A 2.1 in committed checks. You ultimately took a deal, which, look, I don't know what it was. But, you know, CSI rarely pays above one, two x on a deal. Maybe, obviously, if you stay for ten years, can get extra juice. But it wasn't a flashy multiple that you sold for. So why exit? Why not stay yourself and keep building?

Why Jason sold to CSI and deal structure

Jason Pearsall

14:58>> I was tired. And what I mean by tired is not like I wanted to I didn't want to grind for the company. I wasn't sleeping because I had staff to pay. I was running around spending time with investors and not in the operations of my business. And the business was doing well, and I didn't think we had good processes. And I wasn't involved in solving those problems because I was more worried about going to beg people

15:23>> for checks and playing that game. And I had played it for fifteen months. And I wanted, and I had built this business to operate and to grow the business, to work in my vertical, to work with golf course operators and solve their problems. That wasn't what I was doing at all. And so ultimately, including the VCs, the early VCs that did put in some money, participated in our Angel Round, which we're really lucky, another story to

15:46>> participate in. But anyways, like we looked at what the possibility of the earnout was, and it was, and is very significant. And ultimately, you know, the numbers made sense to us, and, you know, we just thought this was the best path.

Nathan Latka

16:04Yeah. Constellation, guys, is a publicly traded company, you can go look at their earnings calls to see the numbers, but it's incredible. I'm going off memory here, but I'm pretty sure they spit off a billion dollars of free cash flow last year. So it is a again, it's a massive, massive holding company of thousands of software companies. Jason, let's shift the focus here to the growth story post close because going from 500,000 of revenue to 9,000,000

16:23of revenue in May is pretty darn impressive in a niche. What have been the top, like, one or two growth channels for you?

Jason Pearsall

16:31>> Look, we only have two we service golf courses, and it's very clear who our buyers are. I can tell you at every golf course who runs that golf course, who the golf professional is, what software they're using, when their contract's up. And so when you have a very small niche, it's all about data, and it's all about knowing how to action the data. And so we're very intentional about approaching golf courses that have high signals that

16:55>> they're going to be making a transition. Same with multi operators. It's been another fuel of our growth, that there's been a lot of consolidation where we can win one deal and win 100 accounts, where in the past, you haven't been able to do that.

17:11>> One multi course operator represents 100 golf courses. So we've won a couple of those, and then we've just gotten better at selling. But the other element is, a big part of it is just investment in product. I mean, there's significant investment into product that's enabled us to build a superior solution. When you

17:32>> have likely the best technology for the customer in the vertical, know, you kinda get out of your own way and just let the technology work.

Nathan Latka

17:41Mhmm. Yeah. I mean, Jason, there's a lot of the really good products that are best in the market that nobody ever hears about, so they never win like you're winning. So you really have to have both. I'm gonna try and push you here to actually jump into, like, concrete tactics. Right around that acquisition date, your domain rating spiked. It looks like there was a real effort around SEO right around that acquisition date. If so, is that

18:00true? And and to what degree is SEO important for Club Caddy's growth?

Jason Pearsall

18:04>> Yeah. Look, of course, it's true. And that was just one of the elements of the SEO wasn't a priority, even when we didn't have the capital as an early stage business to invest in SEO. And we recognized that SEO investments take time to get an ROI on. And so we couldn't make decisions that were eighteen months into the future that sometimes you have to be able to make. It just, we weren't funded to do that, right?

18:27>> And so, yeah, certainly a priority. That was the case. And now the focus is AEO, but definitely a priority.

Nathan Latka

18:36And one of the things you have built into your product is it looks like when you launch the software to your customers, they're hosting it, it looks like on a sub domain, which naturally builds your backlinking strategy, which is like what we see here. Was that intentional or is that just a function of how the product works?

Jason Pearsall

18:51>> A little bit of both, honestly. So each of those could be like a different chunk of locations. They may be on a certain part of the region or country, and we'd route a server to that part of the country for faster performance. It could be a multi course operator who wants their own individual database, doesn't want their customer shared with somebody else. It could be a government or park entity that needs the same. So there's both

19:12>> factors that go into it, both practical and intentional.

Nathan Latka

19:15Mhmm. Interesting. Okay. Are there any other, like, practical tactics like this that you've used? So SEO is one. Are you doing any, for example, paid ads or anything like that?

Jason Pearsall

19:23>> Yeah. Of course. Yeah. So it looks Okay. So tell

Nathan Latka

19:25tell me about how you're using paid to scale.

Jason Pearsall

19:27>> I mean, to grow a SaaS company, each of these are one channel. And you need to have dozens of channels. And at any point, only a couple of those channels are going to be successful. And you just got to continue to try new ones to add that couple to become more and more. But I mean, we go to trade shows. We call every golf course in the country. We try to touch in and physically visit every

19:45>> golf course in a certain cadence every year. We invest in AEO marketing.

Nathan Latka

19:50Who's doing that, though, Jason? Right? So, like, how big is a team today? And do you have AEs that are responsible for making x amount of phone calls to touch all those golf courses each year? How is that structured?

Jason Pearsall

19:58>> Yeah. The entire BDR team. BDRs are, I don't know, have quotas. They've got a we touch every golf course every quarter. A different contact point within that golf course, too. It's not always the one person that you reach out that makes the decisions and tells you no. So it's important to go wide and deep in the organization. And so yeah, we've got full resources within our team to manage each of these, both inbound and outbound.

Nathan Latka

20:26And on the paid side, is that mostly happening on Facebook, or where are you spending paid dollars?

Jason Pearsall

20:31>> No, primarily Google, just pay per click on Google. We also invest in review websites like Capterra and G2, and where our customers are going to find out where the best solution is. We want to be promoted there. And so

20:46>> ultimately, I think the best thing that you can do as a vertical market software company is put yourself in your buyer's shoes. How is your buyer going to shop? What are all the different ways that your buyer is going to come across software? Is it going to be mouth to mouth and basically or word-of-mouth, rather, in the golf course next door recommending something? If so, you should have a recommendation program set up and be loud and

21:07>> clear about why you want advocates and what they get out of it. That's one channel. Is it going to be a trade show? Does somebody only communicate in person? Does somebody All of these are just different buyer profiles, and we try to go after every single one and every opportunity at a golf course, especially when you only have a limited number of golf courses. Like for us, there's 15,000 golf courses in North America. Seven eight thousand

21:29>> are within our ICP. Ultimately, three to four contacts per golf course. There's 35,000 people that we need to get in contact with them multiple times a year. With strategy, time, and resources, that's not a challenge to do.

Nathan Latka

21:44Mhmm. Mhmm. That makes a lot of sense. Yeah. So to summarize here, these are the 33 growth tactics I hear most commonly when I interview CEOs, and, you we're 3,800 interviews in. So we see over and over. Just to summarize ones that you're using, it sounds like really well, as you obviously mentioned review sites down here, right, so Capterra G2. You mentioned programmatic, obviously, SEO, which we just talked about. You mentioned account based marketing. Right? You

22:04built a target list that you just described, and you also mentioned Google Google Ads right down in this this area. Anything else on this screen that you you're using working really well for you? Are you guys pursuing inorganic growth via acquisitions?

Jason Pearsall

22:15>> Always. Yeah. Mean, it's part of the CSI model. And definitely, are. And we just it's not something that I really measure because that's measured amongst our M and A team, we look for synergies across the group. The big one is automated engine optimization. So we intentionally are making investments to make sure when somebody asks ChetGPT what the best golf management software is, they're finding us, right? So that is different than SEO. Yeah.

Nathan Latka

22:43And so, I mean, tell me how you do that. A lot of people say, No one actually knows how this algorithm here actually works. But you're saying you have a general idea and it can be optimized?

Post-acquisition growth channels and tactics

Jason Pearsall

22:52>> Yeah. So, ultimately, look, I mean, you do know. It does give you the answers, right? So it tells you right there that Capterra is a huge source of it. It tells you then best country club management software. So you'll go to these sites, you'll look at where is AEO searching. But more importantly, golf course, product can be found by answer engines if they have a schema. Not sure if you're familiar with schema, but I think it

23:20>> was late '90s, beginning of web domains, there was something called schema.org. And they basically said, we need to have a common set of structured data so we understand how to interpret a website. This is what AEO looks for is schema. And so, you know, when we've invested in optimizing schema, in going out and where GPT is looking for sources, trying to be relevant and at the top of those places so that you're found in those results.

23:46>> It's an ongoing effort. Would

Nathan Latka

23:49you say it's an advantage or disadvantage? So something like this, right, Capterra obviously is a property you do not own, right? So you can pay to play there. Some of your competitors like Lightspeed, they actually own and they're ranking as a direct source, a source of truth in the AEM, and then I don't know what Xelliss is, but how do you think about building your own and operated source of truth for an AU optimization perspective versus

24:10the pay to play models like Capterra?

Jason Pearsall

24:12>> I mean, think you have to do both. It's just like trying to rely on a single channel and hoping that it's going be effective. The most effective will be the combination of all of those. I think we also get a little bit more intentional. And so we're going to say like, search semi private golf course software, something that's where we're trying to understand ourselves. And those are the keywords that we focus on. So it's not just

24:32>> like, let's go at the top of the funnel on keywords. It's trying to be strategic of what are the keywords that my ICP is searching for, and making sure that I'm number one there and not just everywhere.

Nathan Latka

24:43Smooth And at

24:44before we wrap, just to put a cap on ChatGPT, do you have a sense of how much traffic it's driven you over the past year or past month?

Jason Pearsall

24:50>> I don't. I I know that we have now added within HubSpot is the lead source and origin source, and there's been a couple dozen this year that have come in through it. But, you know, we just started tracking it within the last six, All seven

Nathan Latka

25:04right. Well, Jason, you've also launched a new project. You're getting you're still doing software, but tell us about the new project, where you're getting your hands dirty on a new course.

Jason Pearsall

25:13>> Yeah.

25:14>> I had the opportunity to take on a long term lease of a Donald Ross golf course that was purchased by a municipality and ultimately had been abandoned is not the right word, but it was running to the ground. And so the golf course was dead. It wasn't open for a season. All the greens had died. Everything was overgrown. There was a lot of deferred maintenance that hadn't been maintained in a couple of decades. And so I

25:41>> took on a long term lease for a golf course called Warren Valley in 2022, and we did a complete restoration of the facility, tee to green, all new cart paths, all new greens, all new tee boxes, I mean, every complete bunker restoration of the original bunker, or the original Donald Ross design. And then we had documented the whole story. So about a month ago, we launched this channel called Golf Follies, and, you know, really goes through

26:10>> the whole story of that restoration.

Nathan Latka

26:12And is the media platform you're building here, are you getting leads from Instagram as it's driving customers?

Jason Pearsall

26:17>> Can't believe it. It's been incredible. Like we thought we'd build we'd get this story out and build a pipe for it and benefit from it in spring. We rolled it out in October, the end of October, and all throughout November, every single day, we had golfers coming in asking about the Instagram page or mentioning the Instagram page. So cannot believe how much success we've had with it.

Nathan Latka

26:38I mean, obviously, I'm pushing for little mini viral hooks here. But can you quantify the dollar value of golfers that Instagram has brought you from this page?

Jason Pearsall

26:46>> I mean, if every day is, let's say, four to eight golfers, and every foursome's $250 right? So you're looking at thousands of dollars a week. And this is wild. Minimal effort in forty five days of work, honestly, we've had a lot of fun doing it. So it's not a it hasn't even been it's been the most fun marketing campaign I've ever done.

Nathan Latka

27:05I love that. Alright, Jason. Let's ravel here with some rapid fire questions. Number one, how old are you?

Jason Pearsall

27:09>> I'm 41.

Nathan Latka

27:1141. Okay. Something you wish you knew back when you were 20 years old.

Jason Pearsall

27:14>> Enjoy the journey. I always wanted the outcome, to get to where we're at, you know, now. And truthfully, like, the days are easier now, but they're not as fulfilling and they're not as fun.

Nathan Latka

27:25Guys, there you have it. Launched Club Caddy back in 2015, did a seed round of $600,000 scaled about $500,000 of ARR in 2019 before selling to CSI Constellation in 2020. Wasn't a massive exit, but the long term earn out, the potential was really there. So he's still there now building. The company is now doing about $9,000,000 of revenue servicing hundreds of golf courses around the country. He's continuing to scale and now obviously is restoring one of

27:49his own golf course he's got a long term lease on and documenting it to drive property. So he's got his hands in the weeds. He's not just a software guy with no golf experience. It's in his family. Jason, thank you for taking us to the top.

Jason Pearsall

27:59>> Appreciate you, Nathan. Thank you.