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From $450K to $9M ARR in 5 Years: Club Caddie’s Vertical SaaS Playbook
12/03/2025
From $450K to $9M ARR in 5 Years: Club Caddie’s Vertical SaaS Playbook
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.
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