From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook

SaaS Interviews with CEOs, Startups, Founders

Nathan Latka

Entrepreneurship, Business

4.6 • 683 Ratings

🗓️ 3 December 2025

⏱️ 28 minutes

🔗️ Recording | iTunes | RSS

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Summary

Golf course SaaS founder Jason Pearsall shares how Club Caddie scaled from $450K to $9M ARR in 5 years, sold to Constellation Software (CSI), and keeps growing with 600+ golf courses paying ~$15K ACV. If you're building vertical B2B SaaS, this is a masterclass in niche focus, capital efficiency, and smart deal-making.

Jason breaks down why he built an end-to-end ERP for golf courses, how he used data-driven outbound, review sites, SEO and "answer engine optimization" (AEO) to win market share, and what really happened during his CSI acquisition and long-term earnout. We cover pricing, ACV targets, GTM channels, fundraising vs. selling, and how to design a growth engine when your entire ICP is just 15,000 accounts.

In this episode, Club Caddie founder & CEO Jason Pearsall breaks down how he:

Built a vertical SaaS ERP for golf courses after buying and operating his own club
Scaled Club Caddie from $450K to $9M ARR in 5 years with ~600 customers and ~$15K ACV
Raised just $600K before being acquired by Constellation Software (CSI)
Structured a long-term earnout instead of a flashy headline multiple
Used data-led outbound, review sites (Capterra, G2), SEO, and AEO (answer engine optimization) to win in a niche
Built a target list of every golf course, including who runs it, what software they use, and when contracts expire
Turned multi-course operator deals into 50–100 account wins from a single sale
Organized his BDR + AE team to touch every account on a consistent cadence

What you'll learn:

Founder story & capital strategy

How Jason went from golf course operator to SaaS founder
Why he raised only $600K seed and then chose CSI over closing a full Series A
How he thought about risk, fatigue, and opportunity cost when deciding to sell

Revenue, pricing & margins

How Club Caddie reached $9M+ in ARR with 600+ customers
Why they target $15,000+ ACV / ARPO per golf course
How complex, multi-venue golf facilities drive higher contract values

GTM, outbound and channel mix

Why vertical SaaS is a data game when your entire ICP is ~15,000 accounts
How his team touches every golf course every quarter, across multiple contacts
The role of Google Ads, review platforms, trade shows, and word of mouth
How they use multi-course operator consolidation as a growth multiplier

SEO & "Answer Engine Optimization" (AEO)

Why traditional SEO became a priority post-acquisition
How they implemented schema.org and structured data to win AEO
How to intentionally show up when buyers ask ChatGPT and other answer engines for "best golf management software"

Acquisition & long-term upside

Why Constellation Software was the right home for Club Caddie
How a small cash component + long earnout can still be a huge win
What Jason wishes he knew earlier about enjoying the journey, not just the outcome

If you're a B2B SaaS founder, investor, or operator building in a niche vertical, this episode gives you concrete tactics for pricing, GTM, data strategy, AEO, and selling your company without killing long-term upside.

Transcript

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0:00.0	Back in 2020, what were you at in terms of revenue?
0:02.6	Our revenue was only 450,000 in 2019.
0:05.8	Going from half million of revenue to nine million in five years, it was pretty darn impressive.
0:09.6	Ended up selling Club Caddy II Constellation in 2020.
0:12.6	CSI is the largest acquire of vertical market software companies in the world.
0:17.2	On average, we look for about an average of 15,000 ARPU per unit.
0:20.8	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 an ARR today. Would it have been the top like one or two growth channels for you?
0:37.7	You know, we've just gotten better as. All right, folks, I'm here today with Jason Pearsall.
0:41.1	He's the founder and CEO of Club Caddy, a leading golf course management and software company.
0:46.1	He's a lifelong entrepreneur and golf course owner-operator. He blends this technology, data,
0:50.7	and real-world golf operations to help the facilities grow their revenue, improve efficiency,
0:55.4	and deliver exceptional golfer experiences across the country. Jason, you're ready to take us to the
0:59.5	top? Yeah, Nathan, thanks for having me. The margin profile on running a golf course versus the
1:04.1	software for the golf course are very different. They can be. Yeah, I mean, yes. For you,
1:10.1	which came first as we get some of your backstory here.
1:12.4	Were you an owner-operator first or did you build the software, then buy a golf course?
1:16.4	Yeah, that's an interesting backstory. So my father was a country club general manager. I worked at a
1:21.4	golf course my entire life. After college, got involved in early stage startup. had an exit and i bought a golf course
1:29.0	then in operating our golf course recognized that there wasn't a SaaS solution that was designed
1:36.2	to handle a club you know like we had purchased uh and started started building a SaaS solution in
1:41.7	2015 that became club caddy and it's ClubCady today.
1:46.6	That's great. Okay, so before we get the full backstory, I don't want to bury the lead.
	...

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