About

Helping Business Leaders Navigate the AI Era

John doesn’t just follow AI: he has spent four decades building, deploying, and advising on it. As founder-CEO of Rule 30, he delivers executive AI briefings and workshops grounded in real implementation experience, not vendor-driven hype.

His approach is direct and pragmatic: cut through the noise, identify what actually matters for your business, and build a clear path forward.

AI Strategy at Constellation Software (2013-2024)

John held senior leadership roles at Constellation Software Inc. (CSI), one of the world’s most successful software acquirers. As CEO across Softlink Information Centres, Edumate, and Pegasus Systems (and as a mentor guiding 30+ acquisitions) he built a track record in applied AI strategy that few advisors can match:

• Coached dozens of CSI businesses on AI readiness (2019-2024): preparing niche B2B software companies for the AI disruption before it became unavoidable
• Guided CEOs through AI adoption decisions, data readiness assessments, and operational integration
• Championed low-cost, high-impact ML use cases in businesses with rich domain-specific data
• Developed bootcamps and internal advisory tools that moved teams from AI anxiety to AI action

That combination (deep technical roots, capital-allocation discipline, and a decade coaching executives through real AI transitions) is what makes John’s briefings different. He’s already seen how this plays out inside dozens of organisations.

Today, through Rule 30, John delivers executive AI briefings, runs AI Evolution workshops, and contributes to the broader dialogue via podcasts, lectures, and published insights.