SaaS Interviews with CEOs, Startups, Founders

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

12 snips

Dec 3, 2025

Jason Pearsall, Founder and CEO of Club Caddie, scaled his vertical SaaS ERP for golf courses from $450K to $9M ARR in just five years. He shares his journey of building a tailored product to solve real operational issues and highlights the power of data-driven strategies like SEO and AEO for market penetration. The discussion dives into the intricacies of structuring his acquisition by Constellation Software, emphasizing the value of long-term earnouts. Plus, he reveals insights on effective targeting and nurturing relationships in a niche market.

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ANECDOTE

Built Software From Operator Frustration

Jason built Club Caddy after buying and operating a golf course and discovering no suitable SaaS for a full club.
He launched the product in 2015 and used his operator network to get the first customers and early employees.

ANECDOTE

Sold Early To Strategic Buyer With Long Earnout

Jason raised a $600K seed and then nearly closed a $2.5M Series A before Constellation approached him.
He sold to Constellation in 2020 with a small cash component and a long earnout, remaining incentivized through the 2030s.

ADVICE

Weigh Fatigue Against Fundraising

Consider founder fatigue and opportunity cost when debating raising more VC rounds versus selling.
Sometimes trade immediate fundraising pain for a partner that funds product, operations, and growth.

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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.