Aligning with the 2023 Philippines National University Research agenda, this study examines the Basic Education System with a focus on school leadership, policy, and teacher well-being. The research evaluates the satisfaction levels of private senior high school teachers regarding leadership culture and working conditions, specifically analyzing factors such as leadership style, communication, mentoring, environment, and compensation. Employing a mixed-methods, sequential explanatory design, data were gathered from 102 survey respondents and 7 school administrator interviews. Utilizing purposive sampling, the data were analyzed through descriptive and inferential statistics, including linear regression. Results indicate a moderate level of satisfaction across both variables. For "stayers," satisfaction was driven by student relationships, professional development, and democratic leadership. For "leavers," the primary concerns were salary, job security, and management relations. The study also found that age and educational attainment significantly influenced response quality. Synthesizing these findings through the lens of motivators and hygiene factors, the study proposes a faculty development plan rooted in hygiene improvements. The conclusion posits that long-term commitment is fostered through mentorship, growth opportunities, and meaningful recognition. It is recommended that future research quantify the impact of personal attrition factors and validate these findings across diverse geographical and economic contexts.