A lack of effective marketing strategies to stay profitable in the digital age is a concern for small and medium-sized business leaders because it can lead to early business failure, lost revenue, and reduced long-term sustainability. Grounded in relationship management theory and Kotter’s (1996) 8-step change model, this qualitative pragmatic inquiry was conducted to explore effective marketing strategies business leaders use to remain profitable and sustainable beyond 5 years in the digital age. Participants were six business leaders located in the Southeastern United States who had successfully sustained their companies for over 5 years and were directly responsible for marketing strategies. Data were collected through semistructured interviews and thematically analyzed using Braun and Clarke’s thematic analysis process. Six major themes emerged: (a) agile digital adaptation, (b) data-driven decision-making, (c) authentic customer relationships, (d) integration of emerging technology and artificial intelligence for efficiency, (e) organic growth approaches, and (f) leadership for testing and learning. The primary recommendation for marketing professionals, entrepreneurs, and organizational leaders is to foster inclusive, adaptive cultures that encourage innovation and continuous learning to sustain profitability in the digital age. The implications for positive social change include marketing professionals and business leaders implementing ethical and authentic marketing practices to strengthen community ties, promote inclusivity, and empower consumers and employees. By leading with transparency and prioritizing relationship-building, strategic digital marketing leaders can drive economic success while creating more equitable, socially responsible business cultures.