"Tech Titans" don't exist in retail. There are simply those who willingly embrace IT as a core part of the their business and their overall value proposition and there are those who live with outdated sensibilities about IT's role.
If your organization is spending too much time and money maintaining legacy systems, it's because you either made poor decisions in favor of short-term gains or lacked long-term vision. If your IT leader (let's not even assume you have a CIO) is trapped working for your CFO or your IT budget is based on a percentage of your sales, you deserve the spaghetti diagram that is your IT infrastructure.
