We had the good fortune of connecting with Jason Pearsall and we’ve shared our conversation below.

Hi Jason, we’d love to hear about how you approach risk and risk-taking
In navigating my career, I’ve learned that too much caution can be a more significant roadblock to success than the mistakes we often try to avoid. At Club Caddie, we view each error as a stepping stone to improvement, and our ethos revolves around the belief that a project only fails when we decide to give up. This philosophy has empowered our team to approach challenges resiliently, learning from missteps rather than fearing them.

For fellow entrepreneurs, my advice is twofold: First, recognize that risk is not a threat but an inherent part of innovation and growth. Without it, you’re likely moving too cautiously to make any significant impact. Second, foster a culture within your team that sees the value in mistakes. Encourage an environment where learning from errors is accepted and celebrated as a critical component of the development process. This approach fosters resilience and fuels a passion for the relentless pursuit of excellence.

At Club Caddie, we’ve woven this philosophy into our fabric, and it’s been instrumental in our journey. We approach each project with the mindset that true failure isn’t a consequence of risk but a result of giving up too soon. Embrace the risk, learn from every setback, and let your passion be the unwavering guidepost for your journey. In the most challenging moments, we find our greatest opportunities for growth and innovation.

What should our readers know about your business?
Club Caddie’s core difference is our origin: our software is developed by those who have walked in the shoes of golf course owners and operators. This firsthand experience has instilled a profound empathy, shaping our approach to everything from workflow design to support and implementation. We’ve navigated the complexities of software migrations firsthand, experienced the daily grind of using non-intuitive systems, and faced the frustration of explaining system downtimes to unsympathetic customers. This unique perspective ensures our solutions are grounded in golf course management’s real-world needs and challenges.

The legacy systems we aim to replace are relics of a bygone era—non-cloud, server-based systems that have left golf courses and country clubs lagging in technological adoption. Our mission has been to catapult the golf industry into the modern age, leveraging automation to streamline mundane tasks and enhance customer and member experiences with features like self-check-in and on-demand services—our excitement for the future drives this commitment to innovation.

Our journey to this point has been anything but easy. Coming from a middle-class, blue-collar background, raising capital was a formidable challenge. The venture capital community, pre-COVID, viewed golf as a niche and declining market, leaving us with little external funding support. Lacking a robust network of angel investors, we were compelled to self-fund and offer equity stakes in the early stages. Moreover, our initial product offering was too narrow, necessitating several pivots and expansions to deliver value to golf courses. This process demanded time, dedication, further investment, and an unwavering commitment to our vision.

However, through perseverance, strategic resourcefulness, and an unyielding belief in our mission, Club Caddie has become a leading name in golf course management software. Our growth is a testament to what can be achieved with grit, a deep understanding of customer needs, and a vision for a future where technology enhances every aspect of golf operations.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
Since moving here in 2003, I’ve witnessed Detroit’s remarkable transformation and grown deeply connected to its resilience and vibrant culture. If I’m showing a friend around, we’ll dive into the heart of Detroit and attend a local sports game.

Golf would be a highlight of the visit. The area boasts exceptional courses, including the historic Detroit Golf Club and Oakland Hills. We’re also playing Warren Valley, a Donald Ross municipal course in Dearborn Heights that my group manages.

This visit wouldn’t just be about entertainment but a testament to Detroit’s evolution and its people’s vibrant, resilient spirit. From its sports culture to golf courses, Detroit offers a unique blend of experiences reflecting its rich history and exciting future.

Who else deserves some credit and recognition?
To me, the hallmark of an exceptional mentor is someone who invests the time to truly understand the people they’re guiding—recognizing their unique personalities, motivations, and the most effective ways to communicate and inspire them. I’ve received a lot of guidance and support throughout my journey with Club Caddie, but one individual stands out distinctively: Joe Oswald. Now the leader within the Club division at Jonas Software, I consider Joe a mentor.

The transition period when Constellation Software (CSNWF) acquired Club Caddie was a pivotal moment for us, marking our leap from a startup environment to becoming a subsidiary of a public company. It was a daunting transition, filled with frustrations and challenges. Joe’s guidance, patience, and strategic coaching were instrumental in navigating and thriving through these changes. Under Joe’s mentorship, I found more profound professional growth, our startup’s performance significantly improved, and I became a more effective leader.

Website: Clubcaddie.com

Linkedin: https://www.linkedin.com/company/clubcaddie/

Twitter: https://twitter.com/ClubCaddieCom/

Facebook: https://www.facebook.com/ClubCaddieCom/

Youtube: https://www.youtube.com/channel/UC-51-y1_S97PCAm0rv_kRuQ

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