Digital transformation has fundamentally reshaped the strategic management landscape, necessitating new frameworks, capabilities, and leadership approaches to sustain competitive advantage in an increasingly volatile, uncertain, complex, and ambiguous business environment. This research examines how organizations across diverse sectors are reimagining strategic management practices to navigate digital disruption, leverage technological innovations, and create value in interconnected ecosystems. Through a multi-phase investigation involving longitudinal case studies of 42 organizations and survey data from 518 senior executives across 12 industries, this study identifies critical success factors for digital-era strategic management. The findings reveal that organizations with ambidextrous strategic architectures—balancing exploitation of existing capabilities with exploration of digital opportunities—achieve 34.7% higher revenue growth and 28.9% greater market valuation compared to traditionally focused counterparts. The research demonstrates that data-driven strategic decision-making, when combined with intuitive leadership judgment, improves strategic choice accuracy by 41.3% and reduces time-to-decision by 52.8%. Furthermore, organizations that cultivate dynamic capabilities in digital sensing, seizing, and transforming exhibit 3.2 times greater resilience during industry disruptions and recover 2.7 times faster from competitive shocks. The study establishes that ecosystem-based strategies generate 38.4% more innovation output and access to 4.6 times larger market opportunities than traditional vertically integrated approaches. However, significant challenges persist, including legacy system integration difficulties reported by 73.2% of organizations, digital skill gaps affecting 68.4% of transformation initiatives, and cultural resistance impeding 56.9% of strategic change efforts. This paper proposes an integrated Digital Strategy Framework encompassing strategic foresight, adaptive governance, capability development, and cultural transformation to guide organizations through continuous digital evolution. The research contributes to strategic management theory by extending resource-based and dynamic capabilities views to digital contexts while providing practical guidance for leaders navigating digital transformation imperatives.