Jason Pearsall

Founder and CEO of Club Caddie, a vertical SaaS ERP for golf courses that scaled from ~$450K to ~$9M ARR and was acquired by Constellation Software with a long-term earnout.

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Dec 3, 2025 • 28min

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

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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