This study aimed to determine the longitudinal associations between self-reported sleep duration and cardiometabolic disease (CMD) risk in corporate executives. Self-reported sleep duration and lifestyle, occupational, psychological, and anthropometrical, blood pressure and blood marker variables were obtained from 1512 employees at annual health risk assessments in South Africa between 2016 and 2019. Gender-stratified linear mixed models, adjusting for age, lifestyle, occupational and psychological covariates were used to explore these longitudinal associations. Among women, shorter sleep duration was associated with higher body mass index (BMI) covarying for age only (ß with 95% confidence intervals: −0.19 −0.36, −0.03), age and occupational factors (−0.20 −0.36, −0.03) and age and psychological factors (−0.20 −0.37, −0.03). Among men, shorter sleep was associated with both BMI and waist circumference (WC) covarying for age only (BMI: −0.15 −0.22; −0.08; WC: −0.62 −0.88; −0.37); age and lifestyle factors (BMI: −0.12 −0.21; −0.04); WC: −0.016 −0.92; −0.29, age and occupational factors (BMI: −0.20 −0.22; 0.08; WC: −0.62 −0.88; −0.36), and age and psychological factors (BMI: −0.15 −0.22; −0.07; WC: −0.59 −0.86; −0.33). Among men, shorter sleep was also longitudinally associated with higher CMD risk scores in models adjusted for age and lifestyle factors (CMD: −0.12 −0.20; −0.04) and age and psychological factors (CMD: −0.08 −0.15; −0.01). Corporate executives who report shorter sleep durations may present with poorer CMD risk profiles, independent of age, lifestyle, occupational and psychological factors. Addressing sleep health in workplace health programmes may help mitigate the development of CMD in such employees. •Sleep duration and cardiometabolic disease risk were assessed.•Short sleep duration was associated with increased cardiometabolic disease risk.•Potential confounders were included in longitudinal mixed models.•Workplaces could include sleep health to manage cardiometabolic disease.