Background: Pharmacists in Saudi Arabia are assuming increasingly diverse and specialized roles amid rapid healthcare transformation. However, evolving expectations and expanding responsibilities may influence their job satisfaction, well-being, and career stability. This study aimed to assess job satisfaction, burnout, well-being, and career intentions among pharmacists across multiple practice sectors in Saudi Arabia. Method: A nationwide cross-sectional survey was conducted between December 2024 and January 2025 using an electronic questionnaire distributed to licensed pharmacists. The instrument assessed mental well-being, job satisfaction, burnout, workplace environment, and career mobility. Descriptive and inferential analyses were performed using SPSS version 20.0. Results: A total of 531 pharmacists completed the survey; 65% were male, and 89.3% were Saudi nationals. Sector distribution differed significantly by gender (p < 0.001): females were more represented in clinical and hospital pharmacy, while males predominated in the pharmaceutical industry–related roles. Male pharmacists reported higher work environment scores (p = 0.028) and greater sector mobility (34.2% vs. 23.7%, p = 0.012). Approximately 30.5% of participants had changed their employment sector at least once. Community pharmacists reported the highest burnout levels, whereas those in regulatory and administrative roles demonstrated the greatest job satisfaction (both p < 0.001). Participation in professional development showed strong positive associations with job satisfaction and intention to remain in the current role. Conclusions: Marked variations exist in pharmacists’ well-being, satisfaction, and career mobility across sectors in Saudi Arabia, with notable gender differences. Enhancing professional development, ensuring equitable work environments, and promoting sector-specific support strategies may help inform discussions on pharmacist engagement and retention within the evolving national healthcare system.