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

SaaS Interviews with CEOs, Startups, Founders

Release Date: 12/03/2025

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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.