Deal structure and earnout rationale

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

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.