This study explores the determinants of job satisfaction among IT industry employees in the U.S. and South Korea, focusing on how cultural and socio-economic contexts influence employee well-being and organizational sustainability. Given the high turnover rates in the IT industry, understanding the key factors affecting job satisfaction and dissatisfaction is critical for promoting sustainable organizational practices. By comparing reviews from Glassdoor and Jobplanet, this study uncovers cultural and organizational differences that directly affect employee retention and job satisfaction, offering actionable insights for multinational IT companies seeking to align their strategies with sustainable HR practices. The research utilizes Contextualized Topic Modeling (CTM), a cutting-edge method leveraging Sentence-BERT embeddings, to analyze user-generated reviews. CTM identifies key topics such as attendance management, career development, organizational culture, welfare support, salary, and job autonomy, revealing distinct cultural influences. For example, attendance management and organizational culture positively influenced job satisfaction in U.S. companies, while welfare benefits were more significant in the U.S. than in South Korea. Salary had a positive effect in South Korea but a negative effect in the U.S. The comparative analysis also highlights the higher satisfaction levels among current employees, underscoring factors critical for long-term retention. This study contributes to the literature by leveraging user-generated content to reveal context-specific factors, including new elements such as "technological capabilities" and "location and accessibility," which are often overlooked in traditional survey-based research. The findings provide actionable insights for IT companies to refine HR practices in ways that enhance employee satisfaction, contributing to both organizational sustainability and the well-being of employees.