Objective: The aim of the study was to develop tools that quantify employers’ investment in building cultures of health (COH)—inside and outside company walls. Methods: Two COH instruments were developed through literature reviews and expert consultation. The first focused on internal culture of health (COH-INT), that is, programs, policies, and attributes of the physical and social environments that support employees’ health and well-being. The second focused on external culture of health (COH-EXT), that is, programs, policies, and environmental supports that promote communities’ health. We administered these tools to 32 employers and examined instrument reliability, distribution of scores, and correlation between the two instruments. Results: Both tools demonstrated adequate reliability. COH-EXT scores changed minimally over the 3-year study timeframe. There was little correlation between the COH-INT and COH-EXT scores. Conclusions: More research is needed to further develop and validate COH-EXT instruments.