As digital technology has become an integral part of urban’s daily operations; the urban landscape is constantly evolving with the needs of its society. This new reality allowed Municipalities to exert a higher influence in the national and local economy. Through deliberate planning and executing initiatives, they can ignite the local financial ecosystem to growth. In line with this, the paper aims to understand the possibilities available to the Greek Municipalities to exploit the smart city benefits to foster economic development. It is essential to understand the role of different factors including the strategy during the planning and implementing phases of initiatives concerning economy and innovation in a smart city. To achieve this, a tailor-made questionnaire and advanced statistical techniques are applied. The main findings highlight the importance to plan initiatives aligned with the needs of the municipality and the business environment. The existence of a smart city strategy has a catalytic effect on the final impact of the implemented initiatives on the urban environment. A systematic analysis of the smart cities’ dynamics and the new state of the urban environment can help the local actors focus on the value creation and public service provision, fostering innovation and profitability.