The development of marketing has gone from traditional to digital and then AI-powered marketing. The clothing retailer uses AI to reach out to its customers and personalize the shopping experience. As a result of the increasing use of AI-driven marketing, this study also sheds light on privacy aspects, customers place higher demands on marketers to protect the customer’s personal privacy. The Study aims to explore how digital marketing supported by AI, can convert potential customers into actual customers. The study also aims to explore how marketers can address customer privacy concerns related to the collection of personal data. In order to conduct this study a qualitative method with semi-structured interviews has been applied. Interviews have been conducted with marketing specialists, strategists, and managers within ten different marketing agencies. The study has concluded that customer conversion can be enabled by using AI-powered digital marketing tools to provide the customer personalized shopping experience. AI increases accuracy and precision in marketing, the customer can continuously take advantage of offers that are relevant, which in turn increases the chance of a conversion. When it comes to privacy concerns, the marketers describe that it can be reduced with the help of trust building efforts. A policy that explains what AI is and why it is used creates transparency between company and customer. Marketers also believe that the customer should be rewarded with benefits because the customer shares personal information.