In this paper, we examined differences and similarities in wellbeing, mental health, stress, resilience, and perceptions of organisational support and climate between groups of senior leaders, team leaders, and team members across New Zealand (N = 4,215). Results indicated that non-leaders (team members) reported greater stress from non-work life challenges, lower resilience, lower wellbeing, poorer mental health, and more negative perceptions of their organisational support and climate compared to team leaders and senior leaders. Team leaders and senior leaders reported greater stress from work-related challenges (work demands and poor peer support) and lower satisfaction with their work life balance. Mediation analysis found that work factors and resilience significantly mediated the relationship between leadership status (leader versus non leader) and psychological distress and flourishing. Findings support the necessity for targeted interventions for different groups within organisational hierarchies. Further, they emphasise the need for proactive and multi-level approaches to building workplace wellbeing to foster wellbeing in all employees regardless of their leadership status. We make recommendations for organisations to achieve these goals and build psychologically healthy and thriving workplaces.