In recent years, no other sector has seen as much disruption (and innovation) as Retail. Stiff competition from online retailers, smart shoppers who window shop and price match, shrinking foot traffic, high number of temporary staff in stores and warehouses leading to unsatisfactory customer service, security incidents and more has led to reduced customer retention and forced many retailers to cut down on their store count. The Retail chains that are doing well are specialty chains that cater to specific customer needs, or engaging with the customer effectively across multitude of channels. Most retailers are concentrating on Keep The Lights On (KTLO) operation and focusing on reducing their IT spend. However this is counterproductive as customer demand more, not less from the retailers. In response, most retailers want to digitize their operation (Digital Retail) and cut down on technical debt, however are unsure what the Digitization means in their business context and how to prioritize the digitization in a cost effective fashion.