About

John Crook has spent over four decades at the intersection of software and strategy—and was working in machine learning long before AI became a buzzword. From building his first neural network in C in the early 1980s to coaching CEOs through the AI upheaval of the 2020s, he brings a rare blend of technical depth and executive insight to the age of artificial intelligence.

While many discuss AI in theory, John has embedded it into high-stakes business contexts. As founder-CEO of Rule 30, he now advises organisations on how to harness AI responsibly and strategically—especially when decisions must be made under uncertainty, complexity, or regulatory pressure.

His approach to AI is grounded, pragmatic, and refreshingly free of hype—focused on strategy and delivering solutions that actually work.

From 2013 to 2024, John held senior leadership roles at Constellation Software Inc. (CSI), one of the world’s most successful software acquirers. There, he:

• Led strategic acquisitions and coached CEOs across 30+ vertical software companies, guiding them through early AI adoption, data readiness, and operational integration.
• Developed internal bootcamps and advisory tools to help niche B2B companies prepare for AI’s impact across product, pricing, and process design.
• Championed low-cost, high-impact ML use cases in businesses that lacked big budgets but had rich domain-specific data.

This rare combination of deep technical literacy and capital-allocation discipline has made John a sought-after voice in Australia’s fast-growing AI community. He regularly speaks to both technical and executive audiences, demystifying AI's trajectory and highlighting what truly matters for sustainable adoption.

Today, through Rule 30, John delivers executive AI briefings, runs “AI Evolution” workshops, and contributes to the public dialogue via podcasts, lectures, and articles.

Key Milestones on an AI-Centric Journey

• Late 1970s – B.Sc. Physics – University of Sussex, England (studied in French at Université Paris-Sud)
• Early 1980s – Wrote first neural-net program in C, igniting a lifelong AI interest
• 2016–22 – Completed Stanford & Coursera ML specialisations with Andrew Ng et al., formalising modern ML knowledge
• 1980s–2000s – Engineering leadership at British Telecom and Intel; earned patents and led advanced compiler & networking projects
• 2000s–2010s – Rose from developer to CEO at Softlink (Brisbane), focusing on library and education tech
• 2013–2024 – Senior roles at Constellation Software Inc.
• CEO: Softlink Information Centres, Edumate, Pegasus Systems
• Group leader and integration coach for 30+ acquisitions, focused on AI strategy, product fit, and data leverage
• 2024–Present – Founder/CEO of Rule 30: Bridging strategy and ML for organisations navigating the next wave of disruption

Testimonials

·      John’s session and engaging delivery has really helped our business turn abstract concepts into tangible actions.” Sebastian Vaitus, CEO Function Software, Toronto, Canada.

·      John has the rare ability to take complex information and present it in a way that is comprehensible and engaging for audiences of any kind, I can’t wait to hear him speak again! Craig Ford, CEO Function Fox, Vancouver, Canada.

·      John can keep an audience enthused and leaves them wanting more of the education he provided. He takes the complicated subject and simplifies it for all to understand. Syam Menon, Director - Integrations at Volaris Group, London.

·      The session was terrific, a real tour of Intelligence on Artificial Intelligence. Michael Schrage, Massachusetts Institute of Technology | MIT Research Fellow.