Workplace health programs (WHPs) have been shown to improve employee health behaviours and outcomes, increase productivity, and decrease work-related costs over time. Nonetheless, organizational characteristics, including size, prevent certain workplaces from implementing these programs. Past research has examined the differences between small and large organizations. However, these studies have typically used a cut-off better suited to large countries such as the USA. Generalizing such studies to countries that differ based on population size, scale of economies, and health systems is problematic. We investigated differences in WHP knowledge, attitudes, and practices between organizations with under 20 employees, 20−99 employees, and more than 100 employees. In 2017−2018, a random sample of employers from 528 workplaces in Alberta, Canada, were contacted for participation in a cross-sectional survey. Latent Class Analysis (LCA) was used to identify underlying response pattern and to group clusters of similar responses to categorical variables focused on WHP knowledge, attitudes, practices and likelihood of action. Compared to large organizations, organizations with fewer than 20 employees were more likely to be members of the Medium−Low Knowledge of WHP latent class (p = 0.01), the Low Practices for WHP latent class (p < 0.001), and more likely to be members of Low Likelihood of Action in place latent class (p = 0.033). While the majority of workplaces, regardless of size, recognized the importance and benefits of workplace health, capacity challenges limited small employers’ ability to plan and implement WHP programs. The differences in capacity to implement WHP in small organizations are masked in the absence of a meaningful cut-off that reflects the legal and demographic reality of the region of study.