From a childhood without electricity to co-founding a listed betting company, Oliver Shanahan’s story is a masterclass in technical grit and commercial pivots. As the Group Head of Cybersecurity and Infrastructure at BetMakers Technology Group, Oliver traces his path from wiring up early ISPs and mining ERPs to building TopBetta from a two-person LAMP stack into an ASX-listed business. 

In this episode of Tech Execs, James MacDonald sits down with Oliver as he unpacks the high-stakes realities of bookmaking, the decision to pivot from B2C to B2B through acquisitions like Dynamic Odds, Global Betting Services, and Sportech, and why they rebuilt a legacy monolith into a cloud-native, multi-tenant platform that now powers 35+ sportsbooks. We also dig into ISO 27001 in practice, due diligence on tech debt, and how to use AI without leaking your IP. A candid, deeply technical blueprint for founders and engineering leaders navigating scale, regulation, and replatforming you won’t want to miss.