Financial organizations have realised the need to take a relook at their software, to offer the best to their customers. From Know Your Customer to Know Your Bank and now to Know Your Software (KYS), financial organizations have been continuously trying to evolve to enhance the user experience. In the KYS process, organisations have taken a call to retire some of the softwares and apps and adapted newer ones into the system. Any transformation should be phased out. Resilience, agility and cloud readiness of the applications remain critical elements. Replacing or tweaking the existing software and keeping the cost under control is the first step. It is also crucial to understand how can or what are the applications that can be used to measure the readiness, risks attached, which all software should migrate to the cloud etc. The advantage of having all applications on the same dashboard enhances the decision makers to assess the usability. Also the traceability and adaptability play a significant role while choosing the software along with the time taken for migration and scalability. Testing is also as important as any other feature that will look into scalability, security and stability. Testing the system’s down-time and security mitigations are structural issues. Adoption of any new software is like changing the wheels when the train is running. And organizations should be ready for change in the first six months of its launch. In the current era, the financial organisations are competing with the user experience of e-commerce players. Catch Babu Nair of Banking Frontiers in a detailed conversation with Sunil Jain of HDFC Life, KRC Murthy of Kotak Mahindra Bank, Nilkanth Iyer of CAST Software, Sanjeev Kumar of Pine Labs and Mahesh Patel of AGS Transact Tech.