15 - Navigating Startup Acquisition, Growth, and Exits with Jason Pearsall
September 9, 2025
In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Jason Pearsall, CEO of Club Caddie Holdings, about his evolution from startup founder to a private equity-backed business leader. Jason shares his lessons from two successful exits, the pivotal shifts in his golf technology business, and the art of balancing data with instinct. Jason shares his take on the importance of defining your ideal customer profile and a focus on due diligence for sustainable growth. He also highlights why success isn’t always about chasing VC funding but finding partners aligned with long-term goals while transforming traditional industries with technology.
In this episode of 5 to 50: Financial Strategies for Growing Companies, host Jeff Rudner sits down with Jason Pearsall, CEO of Club Caddie Holdings, about his evolution from startup founder to a private equity-backed business leader. Jason shares his lessons from two successful exits, the pivotal shifts in his golf technology business, and the art of balancing data with instinct. Jason shares his perspective on the importance of defining your ideal customer profile and the value of due diligence for sustainable growth. He also highlights why success isn’t always about chasing VC funding but about finding partners aligned with long-term goals while transforming traditional industries with technology.
What you will learn:
- How to identify and pivot when your initial business model isn't meeting market needs
- The critical importance of defining your Ideal Customer Profile (ICP) before scaling
- Why tracking specific KPIs and financial metrics is essential for successful acquisitions
- How to balance founder vision with investor expectations when choosing funding partners
- Differences between managing a startup versus a private equity-backed company
- Why is integrating operational and financial systems is crucial for business scalability
- How to transform traditional businesses through technology
- The essential metrics for running a successful golf course operation
Jeff Pearsall is the CEO and co-founder of Club Caddie Holdings, a comprehensive golf course management software solution. With a background in corporate law and deep roots in the golf industry, Jeff has successfully grown and exited multiple businesses, including leading two golf course acquisitions and achieving a notable exit to Constellation Software. His journey from founding Golfler, an early golf-tech startup, to building Club Caddie into a market leader demonstrates his expertise in scaling technology companies and optimizing golf course operations.
Episode Resources:
- Jason Pearsall on LinkedIn
- Club Caddie Holdings Inc Website
- Jeff Rudner on LinkedIn
- Proseer Website
- Book a Consultation Contact Us
- Download Our eBook: Transforming Accounting Solutions
Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.
Check out our three most downloaded episodes:
Check out our three most downloaded episodes:
- Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial Growth
- The Exit Playbook: Johan Hoernell’s Secrets to Scaling and Selling