Lots of legacy enterprise product suites are being re-platformed to become updated SaaS offerings and offer richer, responsive, device agnostic experiences. While the benefits of such initiatives are many for the business and their customers, it also comes wrought with many major challenges in strategy, technology, time to market and managing change and disruption for the existing customer base. This talk will present a case study and 10 learnings from a 4-year long re-platforming journey of UKG Ready, a HCM product suite. As we follow the journey, we will also learn from UX strategy and contributions at each stage.