The rise of the so called Insurtechs, leveraging digital technologies to offer superior and personalized offerings, has shaken the insurance industry leading to a new age of innovation and business models. In addition, the importance of a digital customer experience is increasing as the number of sales completed online are rising. Customers expect wide availability of personalized options and offerings tailored to their specific risk scenarios. Traditional insurers should react fast to face the threat of new players and remain competitive in this fast-paced market environment. A customer-centric approach to digitalization is required to meet demanding requests from customers while targeting benefits including financial flexibility, lower Total Cost of Ownership (TCO), speed to market, and availability of information anywhere and at any time. Concurrently, the rise of cloud computing technologies spark interests in traditional players that have an opportunity to tackle these challenges by transforming their IT infrastructure to generate value for clients while substantially improving the enterprise’s operations. The aim of this document is to inspire the management to perceive the need for innovation and structural change and provide them with the tools and key recommendations to tackle the challenge. Besides, the literature is lacking contents weighting the cloud computing advantages in the insurance industry and exploring the business model’s innovations necessary to welcome the use of the cloud. Hence, the additional goal of this research, is to address this gap and explore the barriers hindering cloud adoption in the financial services industry together with the mitigation strategies expected to reduce such risk factors.