As global firms face increasing pressure to integrate environmental, social, and governance (ESG) priorities into corporate strategy, leadership has become a critical enabler of sustainable transformation. This study investigates the sustainable leadership and management practices of two global technology leaders—Apple Inc. and Microsoft Corporation—through a comparative case study approach grounded in Stakeholder Theory and Systems Thinking. Utilizing secondary data from corporate reports, ESG disclosures, and academic literature, the research analyzes how distinct leadership styles shape sustainability outcomes and long-term value creation. The findings reveal that Microsoft, under Satya Nadella’s transformational and emotionally intelligent leadership, demonstrates a more holistic and stakeholder-oriented integration of sustainability, exemplified by proactive environmental initiatives and organizational cultural change. In contrast, Apple’s leadership under Tim Cook focuses on supply chain decarbonization and ethical governance, yet faces ongoing challenges in labor practices and systemic supply chain accountability. This study contributes to the growing literature on sustainable leadership by offering comparative insights into leadership-driven ESG integration and provides actionable recommendations for business leaders striving to align profitability with sustainability in the technology sector and beyond.