Today, we dive into the hard-won lessons of digital transformation with Tovi Heilbronn, former digital lead at Harry Rosen and Principal Consultant at Uncork Solutions. From fragile monoliths and business-IT friction to a MACH-powered rebuild that reshaped the customer experience, Tovi shares how his team turned a retail crisis into a strategic breakthrough. He breaks down how they secured executive buy-in, rebuilt trust across departments, and launched both a next-gen ecommerce platform and a clienteling app that brought relationship selling into the digital age. If you’re navigating legacy systems, struggling to align business and tech, or trying to scale without drowning in tech debt, this episode is a masterclass in doing it right the first time and maintaining it for the long haul. Tovi also shares why the real value of transformation starts before a single line of code is written, and how upstream strategy can make or break your velocity.