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

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

Author: Nathan Latka December 3, 2025 Duration: 28:02
SaaS Interviews with CEOs, Startups, Founders
BusinessEntrepreneurship

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.


Ever wonder what the actual numbers look like behind a successful software company, or what crucial decision made the difference between stalling and scaling? SaaS Interviews with CEOs, Startups, Founders cuts straight to that chase. Host Nathan Latka sits down each day for a focused fifteen-minute conversation with the people building the software businesses shaping our world. These aren't abstract discussions; you'll hear founders detail their precise revenue figures, customer acquisition costs, team structures, and the sometimes messy realities of growth. The guests on this podcast represent the full spectrum of the journey, from those just launching an MVP to leaders managing companies with thousands of customers, from bootstrapped operators to those navigating venture funding. By tuning in, you get a daily dose of unvarnished data and tactical stories, stripping away the hype to understand how real SaaS businesses are built, run, and monetized. It’s a resource for entrepreneurs, operators, and anyone curious about the mechanics of modern software entrepreneurship, offering a clear window into the strategies that work and the pitfalls to avoid. Latka’s direct approach ensures every interview delivers concrete takeaways, making this podcast a unique and valuable listen for the business-minded.
Author: Language: English Episodes: 100

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