Podcast Summary

Podcast: SaaS Interviews with CEOs, Startups, Founders
Host: Nathan Latka
Episode: From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook
Guest: Jason Pearsall, CEO of Club Caddie
Date: December 3, 2025

Overview

This episode dives deep into the journey of Jason Pearsall and Club Caddie—a vertical SaaS company serving the golf course industry. Starting with only $450K in ARR in 2019, Club Caddie scaled to over $9M ARR in five years, blending industry insider experience and SaaS execution. Nathan and Jason explore the company’s growth playbook, the pivotal acquisition by Constellation Software Inc. (CSI), funding struggles, channel strategies, and future projects.

Key Discussion Points & Insights

Origins: From Golf Course Owner to SaaS Founder

• Jason’s background: Grew up in golf—father was a club GM, worked summers in the industry.
• Inspiration: After running his own golf course, Jason saw the need for comprehensive, modern SaaS to manage such complex businesses.
  • “Started building a SaaS solution in 2015 that became Club Caddie and is Club Caddie today.” [01:16 – 01:46]

Platform Offerings & Pricing

• Club Caddie is a full ERP system for golf courses, including:
  • POS, inventory, employee management, tee time reservations, membership management, websites, mobile apps, etc.
  • Price varies with customer complexity, but ARPU hovers around $15,000/year.
  • “Golf courses vary, right. Some… may have four restaurants… and some … might have nine holes and a snack bar and one counter.” [01:56 – 02:40]

Customer Acquisition & Network Effects

• Early customers came from Jason’s network of golf course operators and general managers—building for industry pain points.
  • “A couple of general managers that were early users… eventually became the early employees.” [03:47 – 04:33]

Competitive Angle & Product Vision

• Club Caddie aimed to be the first mature full-club cloud solution, unlike older, server-based or immature cloud competitors.
  • “We need to build the first mature cloud solution that services a full club... we carved out our niche.” [04:47 – 05:41]

Growth to 600 Customers & $9M ARR

• Currently serving 600+ golf courses, adding ~25/month, mostly US-based.
• High ARPU driven by deep, industry-specific features.
  • “I can tell you… who the golf professional is, what software they’re using, when their contract’s up…” [16:31 – 17:32]

Bootstrapping, Funding, and the CSI Acquisition

• Self- and friends/family-funded from 2015–2019, raised $600K seed.
• Was preparing for a $2.5M Series A (and had $2.2M committed) when CSI, the largest vertical SaaS acquirer globally, entered with an acquisition offer.
  • “CSI is the largest acquirer of vertical market software companies in the world. They own 2,000 other brands...” [10:44 – 11:10]
• The deal: modest cash up front (enough to make early investors whole), significant long-term earn-out structure due to synergy potential and Jason’s commitment to ongoing growth.
  • “I have the longest earn out in CSI history… well into 2000s I’ll be getting my ROI.” [12:24 – 13:24]

Motives for Selling to CSI

• Jason was exhausted by fundraising and operational juggling.
  • “I wasn’t sleeping because I had staff to pay... I was more worried about going to beg people for checks...” [14:59 – 15:59]
• CSI provided resources, market reach, and potential for a far bigger upside through earn-outs.

Post-Acquisition: The Growth Playbook

Data-Driven, Account-Based Sales

• Small, well-mapped niche means hyper-targeted outbound and personalized lead handling.
  • “It’s all about data, and it’s all about knowing how to action the data.” [16:31 – 17:32]
• Focused efforts on high-signal accounts (contract renewals, consolidations, etc.)
• Partnering with and winning multi-course operators accelerates growth.

Channel & Tactical Execution

• Outbound: Every golf course is regularly touched by the BDR team; wide and deep point-of-contact strategy.
• Inbound/SEO/SEM:
  • Big investment in SEO and Google Ads once capital was available post-acquisition.
  • Review sites (Capterra, G2) targeted as key lead sources and AEO (Answer Engine Optimization) for chatbots/AI-powered searches.
  • “We intentionally are making investments to make sure when somebody asks ChatGPT ‘what’s the best golf management software’, they’re finding us. That’s different from SEO.” [22:16 – 22:44]

AEO & Schema Markup

• “Golf course, every product can be found by answer engines if they have a schema.” [22:53 – 23:49]
• Club Caddie’s site is carefully structured to be read by AI tools like ChatGPT, a newer but growing channel.

Subdomain/Backlink Strategy

• Many customer instances live on unique subdomains, helping with regional performance and backlink profiles.
  • “A little bit of both… practical and intentional [for backlinks].” [18:51 – 19:15]

Paid Marketing

• Mostly Google PPC; review-site promotions; some Facebook, but Google is primary.
• Trade shows, referral/advocacy programs, and account-based marketing round out the playbook.
  • “To grow a SaaS company… you need to have dozens of channels, and … only a couple… are going to be successful…” [19:27 – 19:50]

Inorganic Growth/M&A

• As part of CSI, always considering acquisitions for synergy and expansion.

Media & Secondary Projects: The Warren Valley Restoration

• In 2022, Jason leased and restored Warren Valley, a Donald Ross golf course, documenting it via Golf Follies—a media channel on Instagram.
• The story drove unexpected customer acquisition for the course:
  • “Every single day we had golfers coming in asking about the Instagram page…” [26:17 – 26:46]
  • Quantified as “thousands of dollars a week” in new business, with minimal effort and high engagement.

Notable Quotes & Memorable Moments

• On Early Market Fit:
  “When you build vertical market software, it helps when you are already connected to that industry.” [03:47]

• On Growth Data:
  “When you have likely the best technology for the customer in the vertical, you know, you kind of get out of your own way and just let the technology work.” [17:32]

• On the CSI Earn-out:
  “I have the longest earn out in CSI history…” [13:00]

• On Why Sell Instead of Keep Fundraising:
  “I was tired… more worried about going to beg people for checks… I wanted… to work with golf course operators and solve their problems. That wasn’t what I was doing at all.” [14:59 – 15:59]

• On Vertical SaaS Channels:
  “The best thing… is put yourself in your buyer’s shoes. How is your buyer going to shop?” [20:31 – 21:45]

• On AEO:
  “We intentionally are making investments to make sure when somebody asks ChatGPT ‘what’s the best golf management software’, they’re finding us. That’s different from SEO.” [22:16 – 22:44]

• On the Golf Follies Project:
  “It’s been the most fun marketing campaign I’ve ever done.” [26:46 – 27:05]

Timeline & Timestamps for Critical Segments

| Segment | Key Details & Quotes | Timestamp | |---------------------------------------|------------------------------------------------|--------------| | Growing revenue from $450k to $9M | “Going from half a million… to 9 million…” | 00:05 | | Building the first full-club management SaaS | “We need to build the first mature cloud solution…” | 04:47–05:41 | | Acquisition by CSI | Acquisition rationale & earn-out structure | 10:44–13:24 | | Growth tactics & channels | ABM, outbound, SEO, AEO, paid, M&A | 16:31–24:44 | | Schema/AEO for AI-powered referrals | “You do know it does give you the answers…” | 22:44–23:49 | | Golf Follies story/media as lead gen | “Golfers coming in asking about the Instagram…”| 26:17–27:05 |

Takeaways for SaaS Founders & Vertical Players

• Leverage insider knowledge and industry networks to find product-market fit.
• In vertical SaaS, narrow targeting and personalized outreach scale better than broad campaigns.
• Compounding growth often hinges on winning large, multi-account customers.
• Capital and patient channel investments (like SEO) are easier post-acquisition or as you scale—but initial results often require grit and personal connections.
• Digital tactics like AEO and schema are emerging opportunities, especially as AI-powered “answer engines” gain adoption.
• Media and story-telling—even for a B2B SaaS—can have direct, quantifiable impact on customer acquisition.

In Jason’s words:
“Enjoy the journey. The days are easier now, but they’re not as fulfilling and they’re not as fun.” [27:14]

Host: Nathan Latka
Guest: Jason Pearsall, Club Caddie
Episode Date: December 3, 2025