This exploratory study aims to identify opportunities and challenges within the process of enhancement of the Digital Intensity of Portuguese enterprises in relation to their Martech strategies, including AI, Big Data, Cloud, ERP, and CRM systems’ implementation. An innovative approach to marketing digital transformation is proposed combining the Multilevel Framework for Responsible Digitalization and the Change Engagement model. Such integration is an original contribution to literature, providing a holistic and structured approach to understand and promote digital transformation through responsible and sustainable lens. The analysis considers Martech implementation as constitutive variable of the Digital Intensity Index, and focuses on the Portuguese landscape, discussing recent data retrieved from Eurostat and the national Digital Transition Report in the light of the two theoretical frameworks. A complementary perspective is added interviewing privileged informants, sampled because representing three types of key actors in the implementation processes of Marketing management and Business Intelligence, Digital Communication and Branding, Automation and CRM: enterprises’ managers, Martech service providers and marketing consultants. Our findings cross businesses’ perspectives, showing different strategic approaches to lead with digital transition and transformation and point to three pillars to enhance Digital Intensity, balancing traditional and innovative marketing strategies: digital literacy, sustainability, and stakeholders’ engagement. Main practical contributions emphasize the need for an engaged collaboration between government, business, and civil society actors, aligning their efforts to share responsibilities, co-design adoption strategies, implement actions and shape digitalization policies that ensure participation, sustainability, and fairness in the digital transformation processes and their consequences over time.