Aim: To ascertain empirically the level of career satisfaction and the factors affecting it to achieve a work–life balance. Materials and methods: A cross-sectional study was conducted among dental specialists in Saudi Arabia, using a 25-item online survey questionnaire through emails, social media, and direct interview technique. The questionnaire included factors that measure the job satisfaction in dentistry, like working hours per day, work–life balance, income level, environment of workplace, self-improvement, attitude, and respect from the patient and the society. Data were analyzed using SPSS. Results: Of 315 respondents, the majority were Saudis (68.6%) and males (72.7%). Most of them were satisfied with their work–life balance (63.2%). Almost half of the respondents were satisfied with their current workplace and the opportunities they were offered. Further analysis revealed that most of the respondents will not change their specialty (67.7%) and would recommend their specialty to senior dental students (74.6%). Conclusion: This study showed an acceptable level of satisfaction in almost every aspect (environmentally, psychologically, physically, financially, socially, and personally), great outcomes, and job performance. Nevertheless, some dissatisfaction was identified in the work environment which had a great effect on the overall satisfaction including the availability of materials, the continuous progression in learning and career development, salary, and top officials.