From $450K to $9M ARR in 5 Years: Club Caddie’s Vertical SaaS Playbook
Release Date: 12/03/2025
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info_outlineGolf 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:
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Built a vertical SaaS ERP for golf courses after buying and operating his own club
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Scaled Club Caddie from $450K to $9M ARR in 5 years with ~600 customers and ~$15K ACV
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Raised just $600K before being acquired by Constellation Software (CSI)
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Structured a long-term earnout instead of a flashy headline multiple
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Used data-led outbound, review sites (Capterra, G2), SEO, and AEO (answer engine optimization) to win in a niche
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Built a target list of every golf course, including who runs it, what software they use, and when contracts expire
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Turned multi-course operator deals into 50–100 account wins from a single sale
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Organized his BDR + AE team to touch every account on a consistent cadence
What you’ll learn:
Founder story & capital strategy
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How Jason went from golf course operator to SaaS founder
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Why he raised only $600K seed and then chose CSI over closing a full Series A
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How he thought about risk, fatigue, and opportunity cost when deciding to sell
Revenue, pricing & margins
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How Club Caddie reached $9M+ in ARR with 600+ customers
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Why they target $15,000+ ACV / ARPO per golf course
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How complex, multi-venue golf facilities drive higher contract values
GTM, outbound and channel mix
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Why vertical SaaS is a data game when your entire ICP is ~15,000 accounts
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How his team touches every golf course every quarter, across multiple contacts
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The role of Google Ads, review platforms, trade shows, and word of mouth
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How they use multi-course operator consolidation as a growth multiplier
SEO & “Answer Engine Optimization” (AEO)
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Why traditional SEO became a priority post-acquisition
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How they implemented schema.org and structured data to win AEO
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How to intentionally show up when buyers ask ChatGPT and other answer engines for “best golf management software”
Acquisition & long-term upside
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Why Constellation Software was the right home for Club Caddie
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How a small cash component + long earnout can still be a huge win
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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.